IN THE SUPREME COURT OF THE STATE OF DELAWARE

DJAVON P. HOLLAND, §

§ No. 44, 2016

Defendant Below, §

Appellant, § Court Below: Superior Court

§ of the State of Delaware

v. §

§ Cr. ID No. 1404005828A

STATE OF DELAWARE, §

§

Plaintiff Below, §

Appellee. §

§

Submitted: January 11, 2017

Decided: March 22, 2017

Before STRINE, Chief Justice; HOLLAND and SEITZ, Justices. 

Upon appeal from the Superior Court. REVERSED IN PART.

Benjamin S. Gifford IV, Esquire (Argued), The Law Office of Benjamin S. Gifford 

IV, Wilmington, Delaware, for Appellant.

Karen V. Sullivan, Esquire (Argued), Delaware Department of Justice, 

Wilmington, Delaware, for Appellee.

STRINE, Chief Justice:
This appeal addresses the legal issues raised by the second of two criminal 

trials over a single incident where Djavon Holland—the defendant—allegedly 

burst into an apartment, brandished a gun, and demanded money. A brawl 

unfolded in which Holland and the apartment‘s occupants—Vanessa Grier, 

Nemesis Moore, and Semaj Deshields—were all injured. Holland was indicted 

before the first trial for two counts of Assault First Degree along with twelve other 

related charges. After trial, Holland was acquitted on both of the Assault First 

Degree counts, but the jury was unable to reach a conclusion on the other charges.

The various issues in this appeal stem from the State‘s decision to reindict

Holland. The second indictment included both the charges on which the first jury 

hung, and, for the first time, three counts of Attempted Robbery First Degree. 

After the second trial, the jury convicted Holland of two of the three counts of 

Attempted Robbery and the majority of the other charges from the second 

indictment. On appeal, Holland makes a series of arguments assailing the new 

charges in the second indictment, and attacks the second trial as a whole on Sixth 

Amendment grounds.

Holland challenges the State‘s ability to subject him to the charges in the 

second indictment that were not in the first indictment on three grounds. First, he 

argues that the Superior Court incorrectly interpreted 11 Del. C. § 208. He 

contends the statute in fact bars his indictment for Attempted Robbery. Second, he 
2

argues that the State was estopped from proving all the elements of Attempted 

Robbery of Moore in the second trial. Finally, and most convincingly, he argues

that the new charges constituted vindictive prosecution. We reject his first two 

arguments but find favor with the third.

As to Holland‘s argument that 11 Del. C. § 208 barred the State from 

indicting him on charges not in the first indictment, the Superior Court interpreted 

§ 208(1)(a), which bars new prosecutions for offenses a defendant could have been 

convicted of in an earlier prosecution that resulted in acquittal, to bar the second 

indictment for offenses that were lesser included offenses of the counts previously 

indicted and therefore that the defendant could have been convicted of at his first 

trial. The Superior Court then applied § 208(1)(b)(1) to allow the new charges 

because Attempted Robbery is not a lesser included charge of Assault, and 

Attempted Robbery met § 208(1)(b)(1)‘s requirements that the new charge require 

proof of facts not required by Assault and was intended to prevent a substantially 

different sort of crime than Assault. The Superior Court‘s interpretation of the 

statute makes more sense than Holland‘s interpretation. Holland‘s broader 

interpretation of § 208(1)(a) would, in essence, bar any new indictment on charges 

that conceivably could have been brought in the first indictment. That 

interpretation undercuts the choices the General Assembly made in enacting § 208 

and deprives § 208(1)(b)(1) of any real use.
3

We decline to consider Holland‘s estoppel argument because he did not 

properly present it before the Superior Court and the Superior Court‘s failure to 

separately assess the case for these estoppel claims was not plainly erroneous. If 

we did take up Holland‘s argument that the State cannot prove all the elements of

Attempted Robbery because it is estopped from arguing that Holland caused 

Moore injury or that Holland possessed a firearm, because Holland was acquitted 

by the first jury of Assault in the First Degree and the related Possession of a 

Firearm During the Commission of a Felony, though, we would do so within the 

framework of 11 Del. C. § 208. Using the statute, we would find that Holland‘s 

acquittals at the first trial did not bar his indictment for Attempted Robbery 

because they fit within § 208(1)(b)(1)‘s exception and do not run afoul of § 208(2).

By contrast, we are persuaded by Holland‘s argument that the new 

indictment for Attempted Robbery constitutes vindictive prosecution. The U.S. 

Supreme Court has held that recharging a defendant with different charges after a 

first, inconclusive trial poses a ―realistic likelihood‖ of vindictiveness and due 

process ―requires that a defendant be freed of apprehension‖ of ―retaliatory 

motivation‖ on the part of prosecutors.1 Thus, when the State brings different, 

similarly weighty charges at a second trial, a defendant is entitled to a presumption 

of vindictive prosecution and does not have to prove that a prosecutor was actually 

 

1

Blackledge v. Perry, 417 U.S. 21, 25 (1974) (quoting North Carolina v. Pearce, 395 U.S. 711, 

725 (1969)).
4

improperly motivated in bringing new charges. The State may overcome that 

presumption by showing legitimate reasons why it was unable to present the new 

charges at the first trial. Before and during the first trial, the State had abundant 

evidence that Holland‘s likely motivation for entering the apartment was that he 

believed Moore was a drug dealer who he could rob of cash and drugs. Even if 

Moore testified he was not currently selling marijuana at the time Holland entered 

the apartment, as the State expected he would at the first trial, the evidence 

available to the State such as marijuana and baggies found in Moore‘s bedroom

after the melee, Moore‘s ―weed man‖ nickname, Holland‘s text messages 

suggesting he was targeting Moore‘s apartment for drugs and drug money, and, 

indeed, Moore‘s own statement after the incident that it was possible his apartment 

was targeted because of his reputation, all still would have easily supported an 

Attempted Robbery charge. Indeed, although the State contests that the issue was 

fairly raised, it conceded at oral argument that the presumption of vindictive 

prosecution would apply on these facts.

The State argues that the only reason it recharged Holland was that Moore‘s 

testimony that he was a drug dealer at the time of the incident was the critical piece 

establishing the necessary motive for Holland to rob the apartment. But, nothing in 

the State‘s original theory at the first trial suggested Holland was just wandering 

Moore‘s neighborhood randomly and just happened to pick Moore‘s apartment to 
5

enter because the number on the door inspired violent thoughts. Rather, the 

evidence in the State‘s possession all along supported the inference that Holland 

knew Moore lived there, that Holland needed cash, and targeted Moore‘s 

apartment because he believed Moore was a drug dealer who would have cash and 

drugs on hand that could be stolen. Therefore, the State fails to show a material 

change in the facts available to it to overcome the presumption of vindictive 

prosecution. Because we find that the presumption of vindictive prosecution 

applies, we reverse Holland‘s convictions for Attempted Robbery and Home 

Invasion and the associated counts of Possession of a Firearm During the 

Commission of a Felony, leaving only the convictions for charges from the first 

trial standing.

Seeking total victory, Holland seeks to escape all of the convictions he 

suffered after his second trial by contending that his waiver of his Sixth 

Amendment right to counsel was not knowing, intelligent, and voluntary. We 

disagree. His argument requires accepting both that the Superior Court always

must mechanistically go through a series of factors, which this Court has regularly 

held to be examples rather than a mandatory checklist, and also that the Superior 

Court committed reversible error when it, in part, relied on a colloquy from the 

first trial—before the same judge, less than a year earlier—when it made its 

finding in the second trial that Holland‘s waiver was knowing, intelligent, and 
6

voluntary. When, as here, the Superior Court made its decision to allow Holland to 

proceed pro se only after examining Holland on the majority of factors this Court 

has found relevant and a number of other factors tailored to Holland‘s particular 

motivation for representing himself, this Court declines to fault the Superior 

Court‘s careful decision.

I.2

On April 8, 2014, Djavon Holland burst into Vanessa Grier‘s apartment. 

Grier was at home with her two adult sons, Nemesis Moore and Semaj Deshields. 

Moore had been living with his mother in the apartment for six to nine years before 

the incident.

3

 Holland pointed a gun at Grier and, according to Grier, said ―[g]ive 

me the money.‖4 Moore heard Holland enter and came into the room Grier, 

Deshields, and Holland were in, and confronted Holland. This turned into a brawl 

in which Holland shot his gun several times, injuring Deshields and Moore before 

ultimately being subdued by Grier, Moore, and Deshields. ―Responding officers 

observed that all of the parties were injured.‖5 Although Holland was arguably an 

 

2 Unless otherwise noted, the factual background is taken from the record provided by the parties 

in this appeal.

3 App. to Appellant‘s Opening Br. at A088 (Trial Tr., Jan. 23, 2015); id. at A066 (Trial Tr., Jan. 

22, 2015) (Grier testified Moore lived with her for nine years); id. at A074 (Moore testified that 

he lived with Grier for six to seven years).

4

Id. at A501 (Trial Tr., Sept. 17, 2015). Although the State only elicited this testimony at the 

second trial, Grier refreshed her recollection using her statement to the police immediately after 

the incident, a statement that would have been available to the State before the first trial. Id. On 

appeal, Holland concedes that he demanded money. See Appellant‘s Opening Br. at 8.

5

Id. at 9.
7

armed home invader who sprung upon the occupants of Moore‘s apartment, the 

defenders would seem to have likely been deemed the victors of the brawl if it 

were an MMA title fight. Holland was found by police pinned down under a 

dinner table, bleeding and moaning6and, according to Holland, he suffered the 

greatest injuries and longest hospital stay of the combatants.7 This may help 

explain the comparatively more merciful view the first jury later took of Holland‘s 

actions.

The police found 103 grams of marijuana and baggies used for distributing 

drugs in the apartment. They learned that Moore was known to sell marijuana and 

was nicknamed the ―weed man.‖8 The police also recovered text messages from 

Holland‘s cell phone indicating he was trying to get money—at least $1,5009—as 

well as text messages from a friend of Holland‘s suggesting ―[t]omorrow might be 

better. That way, you could catch . . . the order coming . . . out.‖10 As part of their 

investigation, the police interviewed Moore, who told them he sold marijuana in 

 

6 App. to Appellant‘s Opening Br. at A155–57 (Trial Tr., Jan. 26, 2015); id. at A173–74; see also

id. at A069–70 (Trial Tr., Jan. 22, 2015), id. at A097–98 (Trial Tr., Jan. 23, 2015), id. at A137–

39.

7

Id. at A247 (Trial Tr., Jan. 27, 2015 (Afternoon Session)).

8 App. to Appellant‘s Opening Br. at A031 (Search Warrant, April 9, 2014). Moore 

acknowledged he was aware of the nickname. Id. at A086 (Trial Tr., Jan. 23, 2015).

9

Id. at A550 (Trial Tr., Sept. 18, 2015). Although the text messages do not appear to have been 

used as evidence at Holland‘s first trial, they were obtained as part of the original investigation. 

Id. at A544, A546.

10 Id. at A551.
8

the past but no longer.11 Moore also maintained in his statement that it was 

possible Holland entered the apartment because he knew Moore had been a drug 

dealer.12

On July 21, 2014, Holland was indicted for: 

 Home Invasion (predicate crime: Assault First Degree and/or 

Assault Second Degree)

 Assault First Degree as to Nemesis Moore

 Assault First Degree as to Semaj Deshields

 Assault Second Degree as to Vanessa Grier

 Aggravated Menacing as to Vanessa Grier

 Wearing a Disguise During the Commission of a Felony

 Possession of a Firearm by a Person Prohibited

 Possession of Ammunition by a Person Prohibited

 Misdemeanor Criminal Mischief

 Five counts of Possession of a Firearm During the Commission 

of a Felony

On the morning jury selection was supposed to begin, Holland requested new 

counsel because he was dissatisfied with his public defender. The Superior Court 

determined that a continuance for new counsel was not warranted because the 

request was made on the day of trial and Holland‘s lawyer was otherwise ready to 

proceed.

13

 Instead, the Superior Court asked Holland if he wanted to waive his 

right to counsel rather than continue with his public defender. The Superior Court 

outlined the framework for ensuring that defendants make the choice to waive their 

right to counsel and represent themselves knowingly, intelligently, and voluntarily, 

 

11 Id. at A084 (Trial Tr., Jan. 23, 2015); id. at A437 (Trial Tr., Sept. 16, 2015).

12 Id. at A090 (Trial Tr., Jan. 23, 2015).

13 Id. at A044 (Trial Tr., Jan. 21, 2015).
9

invoking the ―searching inquiry‖ framework from the U.S. Third Circuit Court of 

Appeals decision in United States v. Welty.

14

 That framework has been adopted by 

this Court in cases such as Briscoe v. State.

15 Using that framework, the Superior 

Court asked Holland a series of questions about his understanding of the case, 

experience with the criminal justice system, and education, among other things.

16

 

Based on that colloquy, the Superior Court confirmed that Holland could proceed 

pro se and appointed Holland‘s lawyer standby counsel. 

At trial, contrary to his earlier statement to the police that he no longer sold

marijuana, Moore testified on cross examination that at the time of the incident he 

made money by selling marijuana.

17

 The State later asserted that ―[u]p until the 

eve of trial, the State was not aware that [Moore] was a drug dealer at the time‖ of 

the incident.18 After trial, the jury acquitted Holland of Assault First Degree as to 

Moore and Deshields and the related Possession of a Firearm During the 

Commission of a Felony charges. The jury could not reach a verdict on the 

remaining charges.

After the first trial, the State presented the incident to a new grand jury and 

that grand jury indicted Holland for:

 

14 United States v. Welty, 674 F.2d 185 (3d Cir. 1982).

15 606 A.2d 103, 109 (Del. 1992).

16 See infra Section IV.B. of this Opinion.

17 App. to Appellant‘s Opening Br. at A084, A092 (Trial Tr., Jan. 23, 2015).

18 Id. at A382 (State‘s Response to Defendant‘s Motion to Dismiss, June 1, 2015).
10

 Home Invasion (predicate crime: Attempted Robbery First 

Degree)

 Attempted Robbery First Degree as to Nemesis Moore

 Attempted Robbery First Degree as to Semaj Deshields

 Attempted Robbery First Degree as to Vanessa Grier

 Assault Second Degree as to Vanessa Grier

 Wearing a Disguise During the Commission of a Felony

 Possession of a Firearm by a Person Prohibited

 Possession of Ammunition by a Person Prohibited

 Criminal Mischief

 Five counts of Possession of a Firearm During the Commission 

of a Felony

Before the second trial began, Holland wrote two letters, one to his attorney and 

one to the Superior Court, arguing that the new prosecution was ―vindictive.‖

19

 

Separately, Holland moved to dismiss the charges for Home Invasion, Attempted 

Robbery, and related Possession of a Firearm During the Commission of a Felony 

charges on the basis of the prohibition on double jeopardy and 11 Del. C. § 208. 

The Superior Court denied the motion. 

On the morning of jury selection for the second trial, Holland indicated that 

he wanted to represent himself. Holland and his attorney—Anthony Figliola—

indicated this was specifically related to Figliola‘s advice that Holland testify.

Holland believed that conducting his own defense was a preferable substitute to 

 

19 Id. at A408–09 (Pro Se Letter, Sept. 8, 2015); id. at A413 (Pro Se Letter, Sept. 14, 2015); see 

also infra Section II.C.2 of this Opinion.
11

taking the stand, based on his experience conducting his own defense in the first 

trial. The Superior Court then examined Holland about his choice.20 

The Superior Court concluded that Holland‘s waiver of his right to counsel 

had been knowing, intelligent, and voluntary and proceeded to jury selection and 

pretrial motions. Holland, through Figliola, had made a motion in limine to 

exclude evidence of injury to Deshields and Moore,21 as well as a motion to 

reargue the Superior Court‘s decision that the State could argue, without 

implicating the Double Jeopardy Clause, that Holland possessed a firearm even 

though he had been found not guilty of the Assault charges.

22 The Superior Court 

also invited Holland to ―make any argument you wish over and beyond what was 

set forth in Mr. Figliola‘s motion.‖23 Holland contested his second indictment on 

grounds the prosecutors ―lied.‖

24 The Superior Court denied Holland‘s motion for 

reargument as well as the motion in limine.

25

 

Holland proceeded to represent himself at trial. The State argued that 

Holland wanted to rob the apartment because he ―knew Nemesis Moore was a drug 

dealer and [Holland] knew [Moore] sold marijuana for a living, and [Holland]

 

20 See infra Section IV.B of this Opinion.

21 Motion in Limine to Exclude Evidence of Injury, Sept. 4, 2015, State v. Holland, Cr. I.D. No. 

1404005828A.

22 App. to Appellant‘s Opening Br. at A403 (Motion to Reargue, Sept. 4, 2015).

23 Id. at A425 (Trial Tr., Sept. 15, 2015).

24 Id. at A426.

25 Id.
12

knew that around the neighborhood [Moore‘s] name was  ̳the weed man.‘‖26 After

trial, the jury found Holland guilty of all charges except for Attempted Robbery of 

Deshields and the related Possession of a Firearm During the Commission of a 

Felony, and Wearing a Disguise During the Commission of a Felony.

II.

Holland argues that his second indictment on charges of Attempted Robbery 

was flawed in three ways. He argues both that the Superior Court incorrectly 

interpreted 11 Del. C. § 208 because the statute in fact bars Holland‘s indictment 

for Attempted Robbery, and also that the State was estopped from arguing in the 

second trial that Holland‘s behavior met all the elements of Attempted Robbery of 

Moore. Most compellingly, he argues that the second indictment for Attempted 

Robbery constituted vindictive prosecution. 

A.

We reject Holland‘s argument that the Superior Court erred in its statutory 

interpretation when it concluded that 11 Del. C. § 208 did not bar the charges of 

Attempted Robbery of Moore and Deshields.27 The relevant part of the statute 

states:

Although a prosecution is for a violation of a different statutory 

provision or is based on different facts, it is barred by a former 

 

26 Id. at A577 (Trial Tr., Sept. 21, 2015).

27 Issues of statutory interpretation are reviewed de novo. Fountain v. State, 139 A.3d 837, 840 

(Del. 2016); CML V, LLC v. Bax, 28 A.3d 1037, 1040 (Del. 2011).
13

prosecution in a court having jurisdiction over the subject matter of 

the second prosecution under the following circumstances:

(1) The former prosecution resulted in an acquittal which has 

not subsequently been set aside or in a conviction as defined in 

§ 207 of this title and the subsequent prosecution is for:

a. Any offense of which the defendant could have been 

convicted on the first prosecution; or

b. The same conduct, unless:

1. The offense for which the defendant is 

subsequently prosecuted requires proof of a fact 

not required by the former offense and the law 

defining each of the offenses is intended to 

prevent a substantially different harm or evil; or

2. The second offense was not consummated when 

the former trial began.28

This language is almost identical to the Model Penal Code provision.29 Holland 

argued before the Superior Court that § 208(1)(a) barred the State from indicting 

him for Attempted Robbery of Moore and Deshields, along with the accompanying 

Possession of a Firearm During the Commission of a Felony charges because he 

had been acquitted of the Assault charges against them.30 Before the Superior 

Court and this Court, Holland maintains that § 208(1)(a)‘s phrase ―any offense of 

which the defendant could have been convicted on the first prosecution‖ bars any 

offense that could have been indicted in the first prosecution, but was not. In 

 

28 11 Del. C. § 208.

29 MODEL PENAL CODE § 1.09.

30 Appellant‘s Opening Br. Ex. A at 5. Holland did not make that argument as to the Attempted 

Robbery of Grier, though. Id. at 7.
14

contrast, the State argued that § 208(1)(b) allows the new charges because they are 

different offenses. The Superior Court agreed with the State, observing that 

―[b]ecause the State did not originally indict on those counts, Defendant could not 

have been convicted of those offenses under the original indictment, and thus he 

cannot now claim the protection of subsection (1)(a).‖31 Now, Holland urges this 

Court to find that the Superior Court incorrectly interpreted § 208.

But, the Superior Court‘s interpretation of the statute is the one that better 

gives meaning to each part of the statute in the fashion that the General Assembly 

adopted it. One of § 208‘s handful of deviations from the Model Penal Code text 

is relevant here. The Model Penal Code‘s § 1.09, which § 208 generally tracks, 

includes another provision, which says a prosecution is barred if it is for ―any 

offense for which the defendant should have been tried on the first prosecution.‖32 

Delaware‘s statute, though, omits that provision. Thus, Holland‘s interpretation 

would require this Court to read into the statute words explicitly excluded by the 

General Assembly.

Additionally, the Delaware Criminal Code with Commentary does not offer 

Holland‘s interpretation the support he claims it does when it offers lesser included 

offenses as an example of what § 208(1)(a) bars.33 Holland argues that, because 

 

31 Id. at 6.

32 MODEL PENAL CODE § 1.09 (emphasis added).

33 DELAWARE CRIMINAL CODE WITH COMMENTARIES 19 (1973).
15

lesser included offenses are offered as an example, they are not the exclusive set of 

offenses barred by § 208(1)(a) and, therefore, his circumstance is also barred. 

Even though he is right to observe lesser included offenses are an example rather 

than a complete set, it does not follow that his situation must therefore be included. 

Section 208(1)(a)‘s language could easily cover other situations than Holland‘s, for 

example, a defendant being recharged on charges for which the defendant had 

actually been indicted in the first case.

34

 This illustrates that other examples exist, 

which don‘t suffer from the problems associated with Holland‘s expansive 

interpretation.35

Furthermore, when Holland argues that § 208(1)(a) covers anything that 

could have been conceivably included in an initial indictment, he doesn‘t account 

for what happens to (1)(b). The relevant part of § 208(1)(b) states that a new 

prosecution is not barred if ―[t]he offense for which the defendant is subsequently 

prosecuted requires proof of a fact not required by the former offense and the law 

defining each of the offenses is intended to prevent a substantially different harm 

 

34 See Oral Argument at 22:34, Holland v. State, No. 44, 2016 (Del. Jan. 11, 2017), 

https://livestream.com/DelawareSupremeCourt/events/6861166/videos/146496660.

35 The Model Penal Code Commentaries also undercut Holland‘s interpretation. When they 

address what Delaware adopted as § 208(1)(a), the Commentaries observe that the section is 

meant to ―reach those offenses for which the defendant was in actual jeopardy of conviction on 

the first prosecution‖ and observe that lesser included offenses, attempt or solicitation of offenses 

initially charged, or offenses that differ ―only in that a less serious injury or risk of injury or a 

lesser kind of culpability suffices to establish‖ the offenses all fall within § 208(1)(a)‘s scope. 1 

MODEL PENAL CODE COMMENTARIES 157 (1985). This explanation is at odds with Holland‘s 

broad interpretation of (1)(a). 
16

or evil.‖36 If (1)(a) is actually as broad as Holland argues, it is hard to see how 

there could be any charge that would fit under (1)(b)(1) because (1)(b)(1) plainly 

allows new charges brought on the same conduct when the charges meet certain 

criteria.

Finally, Holland argues that the Superior Court‘s reading makes parts of 

§ 208 incompatible with § 207, which bars prosecutions for ―a violation of the 

same statutory provisions and . . . based upon the same facts as a former 

prosecution‖ under certain circumstances.37 Although the two sections are closely 

related, they are not redundant under the Superior Court‘s interpretation. Unlike 

§ 207, which deals with a prosecution on the same facts and same statutory 

provision, § 208(1)(a) addresses a situation where a defendant is being prosecuted 

on different facts, but for an offense that was part of the events for which the 

defendant was indicted for in the first prosecution. Thus, even under the Superior 

Court‘s reading, the two sections offer subtly different protections for defendants. 

For these reasons, we find the Superior Court properly found that § 208 did not bar 

Holland‘s indictment for Attempted Robbery.

B.

We also reject Holland‘s argument that the State is estopped from proving 

all the elements of Attempted Robbery of Moore because Holland was acquitted by 

 

36 11 Del. C. § 208 (1)(b)(1).

37 Id. § 207.
17

the first jury of Assault in the First Degree and the related Possession of a Firearm 

During the Commission of a Felony.

38

 Holland did not raise this argument 

explicitly before the Superior Court and so this Court reviews the Superior Court‘s 

failure to separately assess the case for these estoppel claims for plain error.39

If this Court considered Holland‘s estoppel argument, it would not embrace

it, much less find a plain error on the part of the Superior Court in not proactively 

considering and accepting the theory. Although Holland frames his argument in 

terms of general principles of estoppel,40 this Court has recognized that, for 

criminal prosecutions, the ―General Assembly has codified the collateral estoppel 

doctrine in Title 11, Section 208 of the Delaware Code,‖

41 and so this Court 

considers the estoppel claim within that framework. This is supported by the 

Model Penal Code Commentaries, which observe that the section of the Model 

 

38 Holland only argues this point on the charge related to Moore because he was acquitted of 

Attempted Robbery of Deshields.

39 ―Only questions fairly presented to the trial court may be presented for review; provided, 

however that when the interests of justice so require, the Court may consider and determine any 

question not so presented.‖ Wainwright v. State, 504 A.2d 1096, 1100 (Del. 1986). If this Court 

chooses to consider such questions, it reviews for plain error. Zhurbin v. State, 104 A.3d 108, 

113 (Del. 2014) (―To warrant review on appeal when the issue has not been fairly presented, 

there must be  ̳plain error.‘ That is, the error complained of must be  ̳so clearly prejudicial to 

substantial rights as to jeopardize the fairness and integrity of the trial process.‘‖ (quoting 

Wainwright v. State, 504 A.2d 1096, 1100 (Del. 1986))); see Brown v. State, 36 A.3d 321, 323 

(Del. 2012) (reviewing appellant‘s sentence for plain error).

40 See Appellant‘s Opening Br. at 24 (―Where a prior judgment of acquittal is based upon a 

general verdict, a court must  ̳examine the record of a prior proceeding, taking into account the 

pleadings, evidence, charge, and other relevant matter, and conclude whether a rational jury

could have grounded its verdict upon an issue other than that which the defendant seeks to 

foreclose from consideration.‘‖).

41 Banther v. State, 884 A.2d 487, 492 (Del. 2005).
18

Penal Code which Delaware codified as § 208(1)(b) ―defines the scope of res 

judicata,‖

42 the doctrine of which collateral estoppel is considered a part,43 as well 

as the Delaware Criminal Code With Commentary, which describes § 208(2) as 

―giving collateral estoppel effect to a former prosecution.‖44 

Here, 11 Del. C. § 208(1)(b)(1) allows the indictment for Attempted 

Robbery. That section allows second prosecutions for the same conduct when 

―[t]he offense for which the defendant is subsequently prosecuted requires proof of 

a fact not required by the former offense and the law defining each of the offenses 

is intended to prevent a substantially different harm or evil.‖45 Attempted Robbery 

in the First Degree requires a jury to find beyond a reasonable doubt that:

(1)The defendant‘s conduct must have occurred in the course of 

committing theft, or in an attempt to commit theft; and

(2)The defendant must have used or threatened the immediate use of 

force on another person . . . ; and

(3)(a) The defendant must have acted with the intent to prevent or 

overcome the resistance to the taking of the property or to the 

retention thereof immediately after the taking; or

(3)(b) The defendant must have acted with the intent to compel the 

owner of the property or another person to deliver up the property; 

and 

(4)(a) In the course of the commission of the commission of the crime 

or the immediate flight therefrom, the defendant (1) caused 

 

42 COMMENTARIES, supra note 35, at 165.

43 See, e.g., 50 C.J.S. Judgments § 926 (―The doctrine of res judicata encompasses four 

preclusive effects that a final judgment may have upon subsequent litigation . . . bar, merger, 

direct estoppel, and collateral estoppel.‖).

44 DELAWARE COMMENTARIES, supra note 31, at 20.

45 11 Del. C. § 208(1)(b)(1).
19

physical injury to [the victims] or (2) displayed what appeared to 

be a firearm . . . .

46

In contrast, Assault First Degree requires a jury to find beyond a reasonable doubt 

that: ―[t]he defendant caused serious physical injury [to the victim]; . . . [t]he 

defendant acted intentionally; and . . . [t]he defendant used a firearm to cause the 

injury.‖47 There are thus several facts necessary to prove either offense, which are 

not common to both. And, assault and robbery are sufficiently distinct offenses. 

One is against just persons (assault) and the other is against both persons and 

property for the sake of obtaining that property (robbery). Thus, § 208(1)(b)(1) 

allows the second indictment. 

Alternatively, § 208(2), which bars a second prosecution when the former 

prosecution ―necessarily required a determination inconsistent with a fact which 

must be established for conviction of the second offense,‖

48 allows the second 

indictment because at the first trial the jury was instructed that the State had to 

prove Holland intentionally caused ―serious physical injury‖ and used a firearm to 

cause the injury.49 Thus, the jury could have determined that Holland did not 

intentionally cause Moore‘s injuries or that those injuries did not meet the 

definition of ―serious physical injury.‖ Thus, its conclusion did not necessarily 

 

46 App. to Appellant‘s Opening Br. at A588 (Trial Tr., Sept. 21, 2015).

47 Id. at A252 (Trial Tr., Jan. 27, 2015 (Afternoon Session)).

48 11 Del. C. § 208(2).

49 App. to Appellant‘s Opening Br. at A252 (Trial Tr., Jan. 27, 2015 (Afternoon Session)).
20

require a determination inconsistent with Holland possessing a firearm or using it 

to cause injury. Therefore, under either relevant provision of § 208, the State was 

not estopped from proving all the elements of Attempted Robbery of Moore. 

C.

1.

Holland prevails on his final argument challenging the second indictment, 

which is that indicting him for Attempted Robbery ran afoul of the federal due 

process concept of vindictive prosecution. We are confronted with a situation 

where the State had ample evidence from the beginning to charge Holland with 

Attempted Robbery, motivated by Holland‘s perception that Moore was a drug

dealer, even if the State also believed Moore would testify he did not currently sell 

marijuana at the time of the incident. But, the reality is that the State did not 

charge Attempted Robbery before the first trial and exclusively focused on 

Assault. Attempted Robbery was only pressed after Holland proceeded pro se and 

was cleared of the most serious charges at his first trial. Although those facts do 

not implicate 11 Del. C. § 208‘s bars on new prosecutions, they do implicate the 

related federal due process concept of vindictive prosecution, which ―requires that 
21

a defendant be freed of apprehension‖ of ―retaliatory motivation‖ on the part of 

prosecutors.50

The State argues that the vindictive prosecution argument was not presented 

to the Superior Court and thus should be reviewed for plain error.51 Holland 

contends he raised the argument ―repeatedly.‖52 We agree with Holland. In this 

context, ―vindictive‖ does not have the normal meaning of desiring revenge.53 

Rather, vindictive prosecution is a federal due process concept that, generally, on 

reindictment or retrial, the State may not substitute a more serious charge for one 

brought in the initial proceedings.54 This is based on the intuition that prosecutors 

could dissuade defendants from pursuing their rights by holding as-or-more serious 

charges for the same behavior in reserve. As the U.S. Supreme Court described in 

Blackledge v. Perry55:

There is, of course, no evidence that the prosecutor in this case acted 

in bad faith or maliciously in seeking a felony indictment against 

Perry. The rationale of our judgment in the Pearce case, however, 

was not grounded upon the proposition that actual retaliatory 

motivation must inevitably exist. Rather, we emphasized that ―since 

the fear of such vindictiveness may unconstitutionally deter a 

defendant‘s exercise of the right to appeal or collaterally attack his 

first conviction, due process also requires that a defendant be free of 

 

50 Blackledge v. Perry, 417 U.S. 21, 25 (1974) (quoting North Carolina v. Pearce, 395 U.S. 711, 

725 (1969)).

51 See supra note 37.

52 Appellant‘s Reply Br. at 5.

53 ―Disposed to seek revenge; revengeful.‖ Vindictive, AMERICAN HERITAGE DICTIONARY OF 

THE ENGLISH LANGUAGE (4th ed. 2000).

54 Johnson v. State, 396 A.2d 163, 165 (Del. 1978).

55 417 U.S. 21 (1974).
22

apprehension of such retaliatory motivation on the part of the 

sentencing judge.‖ . . . A person convicted of an offense is entitled to 

pursue his statutory right to a trial de novo, without apprehension that 

the State will retaliate by substituting a more serious charge for the 

original one, thus subjecting him to a significantly increased potential 

period of incarceration.

56

In Johnson v. State,

57 this Court confronted a case where a defendant was initially 

indicted for charges that would have resulted in possible penalties of life 

imprisonment and thirty-four years of prison time.58 After a mistrial, the defendant 

appealed, and was later reindicted with charges that would have resulted in 

mandatory life imprisonment, and seventy-four years of prison time.59 This Court 

applied Blackledge, and observed that everything Blackledge ―said about 

indictment for a felony following an appeal from a misdemeanor conviction is 

equally applicable to an enlarged indictment following a defendant‘s successful 

motion for mistrial.‖60 ―The only reason appearing in the record for reindicting the 

defendant on the more serious charges is a statement of the prosecutor . . . that the 

defendant was undercharged.‖61

The situation here fits within the circumstances recognized in Blackledge

and Johnson as giving rise to a presumption of vindictive prosecution, as the State 

 

56 Id. at 27–28 (citations omitted) (emphasis added).

57 396 A.2d 163 (Del. 1978).

58 Id. at 165.

59 Id.

60 Id.

61 Id. at 164; see also State v. Moran, 820 A.2d 381 (Del. Super. 2002).
23

itself conceded.62 There is also a human reality at work in this case. The State 

could not have been pleased to have a defendant like Holland represent himself at 

trial, be confronted with what seemed to be very strong evidence of inexcusable 

and unprovoked criminal behavior, and to walk out of court acquitted on multiple 

major charges and without a conviction on the others. Any prosecutor would feel 

the sting of that. Because the circumstances therefore invoke the presumption of 

vindictive prosecution, the State must show there was some legitimate reason why 

the charges couldn‘t be presented the first time.63 Before we reach the merits, 

though, we explain how we understand Holland to have presented his argument to 

the Superior Court.

2.

Holland first raised the vindictive prosecution argument in two pro se letters 

he wrote to his attorney at the time and the Superior Court—both letters were 

received before Holland elected to proceed pro se. In the first letter, sent to 

Holland‘s attorney and entered into the record, Holland stated his concerns that the 

State knew before the first trial that Moore had a reputation as a drug dealer, 

contradicting what the State, in Holland‘s view, asserted after the fact to justify the 

 

62 Oral Argument at 41:33, Holland v. State, No. 44, 2016 (Del. Jan. 11, 2017), 

https://livestream.com/DelawareSupremeCourt/events/6861166/videos/146496660.

63 820 A.2d at 388; see also 63C AM. JUR. 2D Prosecuting Attorneys § 23 (―[O]nce a 

presumption of prosecutorial vindictiveness is raised, the government must rebut the 

presumption by showing objective reasons for its charges, such as the discovery of new 

evidence.‖).
24

new indictment on Attempted Robbery.64 Holland then stated ―I don‘t want to call 

the State[‘s] attorney a liar, and I won‘t, but I will say that it‘s prosecutorial 

misconduct and somewhat vindictive‖ and cited Johnson v. State,

65 the main case 

where this Court addresses the federal due process concept of vindictive 

prosecution. Similarly, in his letter to the Superior Court, Holland outlined what 

he thought were the State‘s misrepresentations about what it knew before the first 

trial about Moore‘s reputation for being a drug dealer.66 He also expressed 

frustration that his attorney had not raised this argument with the Superior Court. 

Holland then asked the Superior Court to find some way to ―address‖ the State‘s 

alleged misrepresentations to ensure ―this is a fair trial and lying of an official of 

the court of law does not constitute fairness as well as holding back of this 

information by a lawyer or official.‖67 Holland closed the letter, asking ―[p]lease 

stop this maliciousness and vindictiveness, in the interest of justice.‖68 In both 

letters, Holland contrasted the evidence available to the State before the first trial, 

including evidence the State used at that trial, all tending to show the State was 

aware Moore had been a drug dealer in the past and, at a minimum, was perceived 

to be a drug dealer, with the State‘s statements before the second trial that it was 

 

64 App. to Appellant‘s Opening Br. at A408–09 (Pro Se Letter, Sept. 8, 2015).

65 396 A.2d 163 (Del. 1978).

66 App. to Appellant‘s Opening Br. at A413 (Pro Se Letter, Sept. 14, 2015).

67 Id. at 414.

68 Id. at 415.
25

not aware Moore was a drug dealer at the time of the incident.

69

 Thus, we 

understand Holland to mean, when he referred to lying, that he believed the State‘s 

indictment on Attempted Robbery was not based on new information, but rather 

that the State lied when it denied that it could have brought the Attempted Robbery

charges with the information it had before the first trial. Indeed, at oral argument, 

the State conceded the letters raised a vindictive prosecution claim, but argued that 

Holland did not renew the claim before the Superior Court when he was actually 

representing himself.

70

But, Holland raised his vindictive prosecution argument at trial as well. On 

the morning of jury selection, Holland stated that he had a disagreement with his 

lawyer about a point he wanted to make, that ―the prosecutor lied in their motion, 

and I wanted that addressed to the courts.‖71 The combined reference to the State 

lying and his lawyer‘s failure to press the argument refers back to Holland‘s letter 

to the Superior Court.72

Furthermore, on the first day of trial, the Superior Court invited Holland to 

―make any argument you wish over and beyond what was set forth in Mr. 

Figliola‘s motion for reargument filed September 4.‖73 After some back and forth, 

 

69 Id. at A408 (Pro Se Letter, Sept. 8, 2015); id. at A413–14 (Pro Se Letter, Sept. 14, 2015).

70 Oral Argument at 41:33, Holland v. State, No. 44, 2016 (Del. Jan. 11, 2017), 

https://livestream.com/DelawareSupremeCourt/events/6861166/videos/146496660.

71 App. to Appellant‘s Opening Br. at A420 (Trial Tr., Sept. 15, 2015).

72 Id. at A413 (Pro Se Letter, Sept. 14, 2015).

73 Id. at A425 (Trial Tr., Sept. 15, 2015).
26

Holland stated ―I wanted to bring up the fact that the prosecution lied in the last 

motion. I wasn‘t done rearguing that fact, that they lied. And I wanted my lawyer 

to bring that up and he didn‘t bring that up. That basically was my issue.‖74 

Again, this is a return to his rhetoric in the letters, where the State concedes a 

vindictive prosecution claim was raised. Changing tack from its original direction 

that Holland could make any argument above and beyond the motions already on 

the table, the Superior Court replied that the only argument he would hear at that 

point was on the motion in limine. Holland replied: ―if they lying, I can‘t get a fair 

trial if they‘re lying.‖75 By lying, we understand Holland to be referring to the 

State‘s contention that it did not have evidence to prosecute him for Attempted 

Robbery at his first trial. Holland reiterated ―I don‘t think lying constitutes a fair 

trial. For the record, lying doesn‘t constitute a fair trial. And that‘s a violation of a 

fair trial, to be lied about.‖76 The Superior Court then observed that Holland could 

address his concerns on appeal. In combination with the letters, these statements 

adequately brought the issue of vindictive prosecution to the Superior Court‘s 

attention and, in fact, the Superior Court indicated that Holland‘s argument could 

be addressed on appeal. Therefore, we consider the argument as one properly 

presented to the Superior Court.

 

74 Id.

75 Id.

76 Id. at A427.
27

3.

Holland‘s statements below and elaboration on them with the assistance of 

counsel before this Court present us with a situation where the defendant was 

recharged with different, similarly weighty charges at a second trial on essentially 

the same facts as the State possessed before his first trial. The State argues, at least 

with respect to Moore, that it did not have an Attempted Robbery case until it 

learned Moore would testify he was a drug dealer at the time of the incident.

77

 But, 

we do not credit that argument given the large amount of circumstantial evidence 

that had been available to the State before the first trial all tending to show Moore 

had a reputation as a drug dealer, and thus, Holland was motivated to target his 

apartment for the valuable cash and drugs that go along with that occupation. That 

evidence includes Moore‘s ―weed man‖ nickname, the marijuana and baggies 

found in Moore‘s apartment, Holland‘s text messages, and Moore‘s own statement 

to the police at the time of the incident that he had sold marijuana in the past and

he thought it was possible Holland targeted his apartment because he had been a 

drug dealer. And, as the State‘s use of the police reports from immediately after 

 

77 However, at oral argument, the State conceded that there had been sufficient evidence before 

the first trial to prove beyond a reasonable doubt Attempted Robbery of Grier. Oral Argument at 

30:38, Holland v. State, No. 44, 2016 (Del. Jan. 11, 2017), 

https://livestream.com/DelawareSupremeCourt/events/6861166/videos/146496660. We respect 

the candor of this admission.
28

the incident to refresh Grier‘s recollection at the second trial shows, Grier told 

police that Holland said ―[g]ive me the money‖ when he entered the apartment.78

As in Johnson and Blackledge, here ―the central figure . . . is the 

prosecutor.‖79 Similarly, the State here had at least a plausible interest in 

discouraging Holland from proceeding pro se, as he did so successfully in the first 

trial. The prosecutorial vindictiveness concept, though, is ―not grounded upon the 

proposition that actual retaliatory motivation must inevitably exist.‖80 Instead, 

―due process also requires that a defendant be freed of apprehension of such a 

retaliatory motivation . . . .‖81 Thus, the State has the opportunity to demonstrate a 

legitimate reason why it was unable to present the new charges at the first trial. 

But, we are not persuaded that the State could have only pressed its Attempted 

Robbery theory once it knew of Moore‘s actual testimony, given the large amount 

of circumstantial evidence available the first trial. Thus, the State fails to overcome 

the federal due process presumption of vindictiveness and Holland‘s convictions 

for Attempted Robbery and Home Invasion and the associated counts of 

Possession of a Firearm During the Commission of a Felony are reversed. The 

 

78 App. to Appellant‘s Opening Br. at A501 (Trial Tr., Sept. 17, 2015). 

79 Johnson, 369 A.2d at 165 (quoting Blackledge, 417 U.S. at 28).

80 Id. (quoting Blackledge, 417 U.S. at 28).

81 Id. (quoting Blackledge, 417 U.S. at 28) (emphasis added); see also 63C AM. JUR. 2D

Prosecuting Attorneys § 23 (―The vindictive prosecution doctrine seeks not only to alleviate the 

accused‘s apprehension of persecution, but also to prevent the chilling of the exercise of legal 

rights by other defendants who must make their choices under similar circumstances in the 

future‖).
29

convictions of Holland at the second trial on charges that had also been pressed at 

the first trial remain.

IV.

A.

Holland‘s successful challenge to the new charges in the second indictment 

does not invalidate all of the convictions resulting from that indictment, because 

Holland was convicted of several charges that were part of the first trial and on 

which the first jury hung. Holland therefore attempts to avoid all of his 

convictions by arguing that the Superior Court erred in allowing him to represent 

himself at his second trial. If a defendant wants to represent herself pro se, she 

must waive her Sixth Amendment right to counsel knowingly, intelligently, and 

voluntarily.

82

 This Court reviews constitutional claims de novo.

83

 The Superior 

Court is ―entrusted with the responsibility of ensuring that the decision by a 

defendant to represent himself is made intelligently and competently‖84 through ― ̳a 

penetrating and comprehensive examination of all of the circumstances‘ and only 

after bringing home to the defendant the perils he faces in dispensing with legal 

representation.‖85 This Court has adopted the framework articulated by the U.S. 

 

82 Smith v. State, 996 A.2d 786, 790 (Del. 2010); Briscoe v. State, 606 A.2d 103, 107 (Del. 

1992).

83 Smith, 996 at 790; Hall v. State, 788 A.2d 118, 123 (Del. 2001).

84 Briscoe, 606 A.2d at 107.

85 Id. (quoting United States v. Welty, 674 F.2d 185, 189 (3d Cir. 1982)).
30

Court of Appeals for the Third Circuit for the Superior Court‘s examination of a 

defendant seeking to proceed pro se.

86

 This framework states:

The trial court should advise the defendant, for example:

(1) that the defendant will have to conduct his defense in 

accordance with the rules of evidence and criminal procedure, 

rules with which he may not be familiar;

(2) that the defendant may be hampered in presenting his best 

defense by his lack of knowledge of the law;

(3) that the effectiveness of his defense may well be diminished by 

his dual role as attorney and accused.

(4) the nature of the charges,

(5) the statutory offenses included within them,

(6) the range of allowable punishments thereunder,

(7) possible defenses to the charges and circumstances in 

mitigation thereof, and

(8) all other facts essential to a broad understanding of the whole 

matter.87

Although the U.S. Court of Appeals‘ language treats the eight factors as examples, 

in some later cases this Court has referred to the Welty factors as a mandatory set 

of items to be discussed.88 But, even when this Court has used relatively 

mandatory language, it has also observed that ―[a] knowing and intelligent waiver 

can occur without reviewing each of [the Welty factors].‖

89 In a more recent case 

this Court introduced the Welty factors as examples of what the Superior Court 

 

86 Id.

87 Id. at 108 (quoting Welty, 674 F.2d at 189).

88 E.g., Smith, 996 A.2d at 790 (―The trial judge should consider the defendant‘s background, 

experience, and conduct, and advise the defendant [of the eight factors].‖); Boyer v. State, 985 

A.2d 389, 2009 WL 3841973, at *1 (Del. Nov. 16, 2009) (TABLE) (―The trial court should 

advise the defendant [of the eight factors].‖).

89 996 A.2d at 792.
31

should discuss with the defendant.

90

 This Court has found that a defendant did not 

effectively waive his right to counsel when the Superior Court did not touch on any

of the Welty factors and therefore did not adequately advise the defendant of ―the 

hazards of self-representation.‖91 Similarly, in Morrison v. State,

92 this Court 

determined that the Superior Court‘s colloquy with a defendant seeking to proceed 

pro se was insufficient because the Superior Court ―failed to inform [the 

defendant] of the nature of the charges, the statutory offenses included within 

them, the range of allowable punishments, possible defenses, possible 

circumstances in mitigation, and the dangers of the dual roles of being an attorney 

and the accused.‖93 By failing to do so, the Superior Court ―failed to conduct  ̳a 

penetrating and comprehensive examination of all the circumstances‘ in order to 

find a proper waiver.‖94 Similarly, in Smith v. State,

95 the Superior Court reviewed 

some, but not all of the Welty factors, the defendant‘s ―answers were not 

responsive,‖ and ―the trial judge never made a determination on the record that [the 

defendant] knowingly and voluntarily waived his right to counsel.‖96 In contrast, 

this Court has also found that a Sixth Amendment waiver was knowing, intelligent, 

 

90 Morrison v. State, 135 A.3d 69, 74 (Del. 2016). But, even in that case this Court observed that 

―the failure of a trial court to substantially adhere to [the Welty] guidelines requires the 

conviction(s) to be reversed.‖ Id.

91 Briscoe, 606 A.2d at 109.

92 135 A.3d 69 (2016).

93 Id. at 74.

94 Id. (quoting Welty, 674 F.2d at 189).

95 996 A.2d 786 (2010).

96 Id. at 791.
32

and voluntary even when the Superior Court did not mechanically go through each 

of the Welty factors.97

B.

At the first trial, the Superior Court asked Holland a series of questions as 

part of its determination that his waiver was knowing, intelligent, and voluntary, 

beginning with ―[s]o do you wish to represent yourself in this case which is going 

forward today?‖ Holland replied ―Yes.‖98 The Superior Court confirmed that 

Holland filled out and signed the waiver of counsel form with the assistance of his 

counsel.99 Then, the Superior Court noted that ―[a]ll the charges are listed on that 

waiver of counsel form,‖ summarized them, and stated the mandatory minimum 

sentence of thirty-three years, and explained that meant ―[t]he Court could not give 

you any lesser sentence, even if it wanted to.‖100 Holland confirmed he 

understood.101 The Superior Court then stated the 242 year maximum sentence and 

Holland confirmed he understood the maximum.102 The Superior Court then 

engaged in the following dialogue with Holland:

 

97 Hartman v. State, 918 A.2d 1138, 1140–42 (Del. 2007).

98 App. to Appellant‘s Opening Br. at A048 (Trial Tr., Jan. 21, 2015).

99 The Waiver of Counsel form, which must be signed by the defendant and the Superior Court, 

states a defendant‘s charges, maximum total period of incarceration, education, previous 

experience with the criminal justice system, and contains a series of statements about the hazards 

of self representation that the defendant has to acknowledge. App. to State‘s Answering Br. at 

B1 (Waiver of Counsel Form, Sept. 15, 2015).

100 App. to Appellant‘s Opening Br. at A048 (Trial Tr., Jan. 21, 2015).

101 Id.

102 Id.
33

THE COURT: Do you believe you are competent to represent 

yourself?

THE DEFENDANT: Yes.

THE COURT: What is the extent of your education?

THE DEFENDANT: I have some college.

THE COURT: And how many years of college do you have and 

where, which college was that?

THE DEFENDANT: Close to two at PG Community, Prince George 

County.

THE COURT: All right. I understand you have previous experience 

in the criminal justice system, in that in 2006, pled guilty to a robbery; 

is that correct?

THE DEFENDANT: Yes.

THE COURT: Do I understand that you have not participated in a trial 

before?

THE DEFENDANT: Yes.

THE COURT: Do you realize that most persons who are charged with 

criminal offenses choose to be represented by a lawyer, and that the 

constitution guarantees you, as an accused person, the right to a 

lawyer?

THE DEFENDANT: Yes.

THE COURT: I understand—do you understand that a competent 

lawyer would be knowledgeable in court—of court proceedings, 

Rules of Evidence and the law that governs your trial? If this case is 

tried, do you understand there may be technical issues, which would 

make it very difficult for you as a nonlawyer to assess?

THE DEFENDANT: Yes.

THE COURT: [D]o you understand that a trial in this case will take 

place according to the established laws and rules of Court and that you 

do not have a constitutional right: A, to receive personal instruction 

from the trial judge on courtroom procedure; and B, to have the trial 

judge take over the chores for you that would normally be attended to 

by a trained lawyer as a matter of course if you have legal 

representation?

THE DEFENDANT: Yes.
34

THE COURT: Do you understand that if you become confused or 

frustrated, there would be no basis to interrupt the trial nor would it be 

permission [sic] for you to raise improper objections or 

representations?

THE DEFENDANT: Yes.

THE COURT: Do you understand if you should fail to conduct 

yourself with due respect for the laws and rules governing your trial or 

if you should become disruptive, it is possible that the trial court, 

that‘s me, might then appoint a lawyer, that would be Mr. Armstrong, 

to represent you whether you liked it or not?

THE DEFENDANT: Yes.

THE COURT: Do you understand that the Court in its discretion may 

appoint a standby lawyer to assist you and offer consultation whether 

you desire a standby lawyer or not?

* * * *

THE DEFENDANT: Yes.

THE COURT: Do you understand there are definite hazards in 

representing yourself?

THE DEFENDANT: Yes.

THE COURT: Nevertheless, do you wish to represent yourself in this 

case?

THE DEFENDANT: Yes.

THE COURT: And do you believe you are knowingly, intelligently 

and voluntarily waiving your right to an attorney?

THE DEFENDANT: Yes.

THE COURT: I will also add that if at any time during the trial, you 

would ask permission to have Mr. Armstrong be admitted as your 

counsel of record, he would then take over the trial. He would then do 

whatever things are necessary, opening statements, cross-examination 

of witnesses, jury selection, closing arguments, et cetera. Do you 

understand that?

THE DEFENDANT: Yes.103

 

103 Id. at A048–49.
35

When, at the second trial, Holland wanted to represent himself, the Superior Court 

engaged in another dialogue with him, again confirming Holland wanted to 

represent himself, that Holland understood the potential length of his sentence, and 

asked Holland a series of questions:

THE COURT: Do you understand that you have the right to be 

represented by counsel, and that‘s a constitutional right?

THE DEFENDANT: Yes.

THE COURT: . . . . But do you understand that Mr. Figliola, or any 

lawyer, is going to be more knowledgeable about court procedure and 

rules of evidence and the law than someone representing himself, who 

hasn‘t been to law school?

THE DEFENDANT: Yes.

THE COURT: Do you understand that you don‘t have a constitutional 

right to receive personal instruction from me as the trial judge on 

courtroom procedure or to have me take over chores for you that are 

normally handled by a trained lawyer as part of the representation?

THE DEFENDANT: Yes.

THE COURT: Do you understand that, if you become confused or 

frustrated, that would be no basis to interrupt the trial and it wouldn‘t 

be any authority for you to raise improper objections or 

representations?

THE DEFENDANT: Yes.

THE COURT: Do you understand that, if you should fail to conduct 

yourself with due respect on the laws and rules governing our trial, or 

if you should become disruptive, then I might appoint a lawyer, in this 

case Mr. Figliola, to represent you, whether you liked it or not?

THE DEFENDANT: Yes.

THE COURT: Do you understand, as in the last trial, if I allow you to 

represent yourself—and it‘s your constitutional right to do so—that I 

would appoint Mr. Figliola as so-called standby counsel? He would 

just be here in Court for the entire trial? He would never address me. 
36

He would just offer you any advice that you may want to ask him 

about?

THE DEFENDANT: Yes.

THE COURT: Do you understand, as Mr. Figliola said, that whether 

or not you take the witness stand or not in your defense is totally 100 

percent your decision?

THE DEFENDANT: Yes.

THE COURT: Do you understand that Mr. Figliola can give you his 

best advice as to whether or not you should take the witness stand or 

not but, ultimately, it‘s your decision?

THE DEFENDANT: Yes.

THE COURT: I gather from Mr. Figliola that his recommendation to 

you is that you take the stand but that you have indicated to him that, 

now at least—you don‘t have to make this decision until the end of 

the—until it gets to be the defense case—that, ultimately, that‘s going 

to be your decision?

THE DEFENDANT: Yes.

THE COURT: I mean, you could have Mr. Figliola represent you 

during the trial but still decide not to take the witness stand. Do you 

understand that?

THE DEFENDANT: Yes.

THE COURT: Do you understand that, if you were to take the witness 

stand, there would be an out-of-jury hearing to determine what crimes 

that you previously were convicted of might be admissible for 

impeachment purposes, meaning going to credibility? That‘s a 

standard procedure in criminal trials. Do you understand that?

THE DEFENDANT: Yes.

THE COURT: All right. Well, I think the defendant has—do you 

believe you have knowingly, intelligently, and voluntarily waived 

your right to counsel?

THE DEFENDANT: Yes.

THE COURT: All right. I find that you have knowingly, intelligently, 

and voluntarily waived your right to counsel. I incorporate by 
37

reference, finding that I made in the first trial, where a similar 

colloquy was had. So, I have signed the waiver-of-counsel form.104

C.

Holland now argues that the Superior Court failed to properly determine that 

his waiver of counsel was knowing, intelligent, and voluntary because, in essence, 

the Superior Court integrated some of its findings from the first trial‘s pro se

colloquy into its determination at the second trial. Specifically, Holland argues 

that the colloquy at the second trial was defective because: i) the Superior Court 

did not confirm that Holland remembered the first colloquy or still understood the 

considerations covered before it relied on some of its findings; ii) the Superior 

Court did not specifically state in the second colloquy that the effectiveness of 

Holland‘s defense could be diminished by his dual role as defendant and attorney; 

iii) the Superior Court did not mention the specific statutory offenses Holland was 

charged with; and iv) the Superior Court did not inform Holland of the range of 

allowable punishments he was facing.105 In doing so, he argues that this Court‘s 

precedents dictate that the Superior Court must explicitly discuss each Welty

factor.

But, the Superior Court adequately determined that Holland‘s waiver of his 

right to counsel was knowing, intelligent, and voluntary. At the second trial‘s 

 

104 App. to Appellant‘s Opening Br. at A420–21 (Trial Tr., Sept. 15, 2015) (emphasis added).

105 See Appellant‘s Opening Br. at 36.
38

colloquy, the Superior Court explicitly covered the first and second Welty

factors.

106

 The Superior Court also spent a great deal of time addressing the issue 

that had seemed to precipitate Holland‘s desire to proceed pro se: when and how 

he might testify on his own behalf. The Superior Court walked Holland through 

the ideas that testifying was his choice alone whether he proceeded with his 

attorney or pro se, that Holland‘s attorney could give him good advice on 

testifying, and that if Holland took the stand it was conceivable that evidence of 

crimes he had been convicted of in the past would be admitted for impeachment 

purposes. Additionally, the waiver of counsel form, which Holland had filled out 

and the Superior Court referred to throughout the colloquy, listed the charges, 

which is the fourth Welty factor.

107

 Already, the colloquy at the second trial was 

more substantial than those in the cases Holland relies on where the Superior Court 

barely covered Welty factors and did not tailor its colloquy to the specific reasons

the defendant wanted to proceed pro se. 

Furthermore, there is no reason for this Court to exclude the Superior 

Court‘s colloquy at the first trial from its analysis of Holland‘s waiver of his right 

to counsel at the second trial. Although Holland now objects that the Superior 

Court did not confirm Holland recalled the first colloquy, both colloquies were 

 

106 ―[T]he defendant will have to conduct his defense in accordance with the rules of evidence 

and criminal procedure, rules with which he may not be familiar‖ and ―that the defendant may be 

hampered in presenting his best defense by lack of knowledge of the law.‖ Welty, 674 F.2d at 

189.

107 App. to State‘s Answering Br. at B1 (Waiver of Counsel Form, September 15, 2015).
39

before the same judge, for trials on the same incident, a little over half a year apart. 

Additionally, the Superior Court explicitly relied on the first colloquy in the second 

colloquy and Holland, or his attorney, who was participating at that juncture, did 

not voice confusion at the time even though there was ample opportunity in the 

colloquy to do so. It is rational, therefore, for a judge who had thoroughly 

reviewed the Welty factors previously with a defendant to carefully tailor the 

second proceeding by focusing more acutely on certain key factors and carefully 

giving the defendant information to make sure his waiver was knowing, intelligent, 

and voluntary. The particular inquiry the Superior Court conducted here reflected 

such an effort.

To this point, consideration of the Superior Court‘s colloquy from the first 

trial helps further demonstrate the robustness of its inquiry into Holland‘s choice to 

waive his right to counsel. For one thing, in the earlier colloquy the Superior Court 

directly addressed the third Welty factor, that the effectiveness of Holland‘s 

defense might be diminished by his dual role as attorney and accused.108 The 

Superior Court also directly addressed the statutory minimums and maximums, 

which addresses the sixth Welty factor. Holland argues that this discussion was 

improperly integrated into the second colloquy because the charges against him 

were partially changed between the first and second trials. But, both Assault First 

 

108 The Waiver of Counsel form, signed by Holland before the second colloquy, also addresses 

this point. Id.
40

Degree, the crime for which he was initially charged, and Robbery First Degree, 

the attempt of which he was charged before the second trial, are classified as Class 

B Felonies under the Delaware Sentencing Accountability Commission‘s 

guidelines and have nearly identical defined maximums and minimums.109 

Although a perfect colloquy would likely have acknowledged the variation, this 

colloquy‘s failure to do so, by itself, is not a sufficient reason to reverse the 

Superior Court.

110

 Thus, between the two colloquys, only the seventh Welty factor, 

possible defenses to the charges and circumstances in mitigation, was left 

unaddressed. Although this Court‘s pronouncements on how to use the Welty

factors in this context have been somewhat confusing, the more recent cases 

emphasize that not every factor has to be specifically addressed in each case. 

Instead, the Welty framework is a guide to use in addressing the Superior Court‘s 

ultimate objective here, which is ensuring defendants understand the repercussions 

and risks of their choice to proceed pro se. Here, the Superior Court addressed 

almost all of the factors and, most importantly, tailored its inquiry to the issue that 

 

109 DELAWARE SENTENCING ACCOUNTABILITY COMMISSION, BENCHBOOK 2015 6, 15, 37–38 

(2015). The difference in the minimum amounted to three years.

110 As the State points out, at the second trial, the Superior Court did explain the maximum and 

minimum sentences. State‘s Answering Br. at 33. But that explanation came after the Superior 

Court found that Holland knowingly, intelligently, and voluntarily waived his right to counsel, so 

it‘s difficult to credit that explanation as part of the colloquy. But, in fairness to the State‘s 

point, the Superior Court did give Holland the opportunity to confer with his now-standby 

counsel and his mother after hearing the minimums and maximums. App. to Appellant‘s 

Opening Br. at A423 (Trial Tr., Sept. 15, 2015). Furthermore, the maximum was listed and 

acknowledged by Holland on the Waiver of Counsel form. App. to State‘s Answering Br. at B1 

(Waiver of Counsel Form, Sept. 15, 2015).
41

was driving Holland‘s request to proceed pro se. The Superior Court‘s generally 

careful work here was sufficient to constitute the sort of inquiry this Court requires

and thus sufficient for Holland‘s waiver of his Sixth Amendment right to counsel 

to be knowing, intelligent, and voluntary.

111

V.

To sum up, the Court reverses Holland‘s convictions for Attempted Robbery

and Home Invasion and the associated counts of Possession of a Firearm During 

the Commission of a Felony because the State failed to overcome the presumption 

of vindictive prosecution. But, because we find that his waiver of his right to 

counsel was knowing, intelligent, and voluntary, and reject his other claims, 

Holland‘s convictions for Assault Second Degree, the related count of Possession 

of a Firearm During the Commission of a Felony, and Criminal Mischief stand. 

The time for filing a motion for rehearing en banc is shortened to five days.112

 

111 Holland, for the first time on appeal, makes another argument attacking the validity of the 

entire trial. He argues that the Superior Court committed plain error when it failed, on its own 

motion, to declare a mistrial when Holland became aware of a supplemental DNA report midtrial, even though the State had disclosed the report six months earlier. At trial, Holland 

successfully objected to the introduction of the supplemental report, App. to Appellant‘s 

Opening Br. at A515 (Trial Tr., Sept. 17, 2015), but then decided he preferred the supplemental 

report to the original one, id. at A519–20 (Trial Tr., Sept. 18, 2015), and consented to its 

introduction. ―[T]his Court has consistently held that a conscious decision to refrain from 

objecting at trial as a tactical matter is a waiver that will negate plain error appellate review,‖ 

Wright v. State, 980 A.2d 1020, 1023 (Del. 2009), and so we do not consider this argument 

today.

112 Supr. Ct. R. 4; id. 18.