Title: MacDonald v. State
Citation: N/A
Docket Number: 220, 2000
State: Delaware
Issuer: Delaware Supreme Court
Date: July 27, 2001

IN THE SUPREME COURT OF THE STATE OF DELAWARE
GLENN E. MACDONALD,
§
§
Petitioner Below,
§
Appellant,
§ No. 220, 2000
§
v.
§ Court Below: Superior Court
§ of the State of Delaware in and
STATE OF DELAWARE,
§ for New Castle County
§ Cr.A. Nos. IN93-03-0550 and
Respondent Below,
§ 0551
Appellee.
§
Submitted: March 13, 2001
Decided:
July 27, 2001
Before WALSH, HOLLAND, and STEELE, Justices.
Appeal from Superior Court.  REVERSED and REMANDED.
Gary F. Traynor, Esquire, Prickett, Jones & Elliott, Dover, Delaware for
Appellant.
Ferris W. Wharton, Esquire (argued) and Thomas E. Brown, Esquire, Deputy
Attorneys General, Department of Justice, Wilmington, Delaware, for Appellee.
WALSH, Justice:
2
In this appeal from the Superior Court’s denial of a motion for postconviction
relief, the appellant contends that he should have been permitted to withdraw guilty
pleas that he claims he entered into without the effective assistance of counsel and
under conditions of duress.  Upon a full review of the record, we conclude that,
given the irregularities in the process leading up to the entry of the guilty pleas —
including the consent of the defendant’s counsel to changing the conditions of the
defendant’s confinement — the disputed guilty pleas were neither intelligently nor
voluntarily entered with the assistance of counsel.  Therefore, the Superior Court
abused its discretion in not permitting the withdrawal of the guilty pleas.
Accordingly, we reverse.
I
This appeal arises from a criminal prosecution that was the sequence to an
earlier prosecution directed against the same defendant, Glenn E. MacDonald
(“MacDonald”).  The first prosecution began with MacDonald’s arrest in 1990 on
a charge of first degree murder in the death of MacDonald’s former girlfriend, Julie
Spencer.  MacDonald was twice tried on the murder charge, with the first trial
ending in a deadlocked jury.  A principal witness against MacDonald was Allan
3
Smith, originally considered a suspect in Spencer’s killing.  Smith testified that
MacDonald had admitted killing Spencer.  At a second trial in February 1993,
MacDonald was found guilty of first degree murder.  Subsequently, his bail was
revoked and he was committed to Gander Hill prison to await sentencing, scheduled
for May 7, 1993.  In the following three weeks, events occurred that resulted in
MacDonald’s accelerated sentencing on the murder charge, his arrest on new charges
of attempted murder and conspiracy to commit murder, pleas of guilty to certain of
the new charges, and surrender of his right to appeal the murder conviction. These
unusual events are briefly summarized.
Shortly after McDonald’s incarceration, a federal agent was contacted by John
Foley, another Gander Hill inmate who claimed to have information on a contract
“hit” related to MacDonald’s trial.  Foley had twice previously contacted the same
agent offering information regarding stolen credit card activity involving one Garret
Markward.  The federal authorities had apparently rejected Foley’s offer of
assistance on those occasions.  Foley’s latest offer of assistance also related to
Markward who, according to Foley, had been suggested to MacDonald as the
possible hitman to eliminate Smith.  The federal agent relayed this information to the
Delaware State Police who, acting with the State prosecutors in MacDonald’s
4
murder trial, made plans to secure evidence against MacDonald on charges of
attempted murder.
Because the information relayed by Foley indicated that MacDonald planned
to use his wife, Tracy, as the contact with Markward, the police secured a court-
authorized wiretap, on March 3, to intercept telephone communications between
MacDonald and his wife, and any other person involved in the alleged conspiracy.
Meanwhile, Foley, acting in concert with the police and prison security officers,
contacted Markward and arranged for Markward to meet MacDonald’s wife in order
to receive $2,500 — one half of the price allegedly agreed upon for the hit.  The
police arranged for an undercover policewoman to pose as Tracy MacDonald for a
meeting with Markward, who was arrested shortly after the delivery of the partial
payment.  After his arrest, Markward admitted agreeing to accept $5,000 to rough
up Smith, but denied assenting to any plan involving Smith’s murder.  Later that
same day, police intercepted a call from MacDonald to his wife in which MacDonald
asked her to meet an individual to discuss financial arrangements for dealing with
Smith.  Police arranged for an undercover officer posing as Markward to meet with
Tracy.  During this meeting, Tracy indicated to the undercover officer that the plan
was to force Smith to write letters disavowing his trial testimony, to hurt him, and
1The transcribed record of the conference reflects the following statement by the prosecutor
and comment by MacDonald’s counsel:
We are extremely concerned about Glenn MacDonald’s current activities
because we have very current; that is, as of approximately an hour and a half ago,
information that even given the fact that Glenn MacDonald knows that his wife is
(continued...)
5
then to make him disappear.  Tracy was unable to immediately supply any funds for
this purpose, and, after unsuccessfully attempting to secure funds from MacDonald’s
parents, promised to pay the undercover officer the following day.  Police, however,
arrested Tracy later that evening on charges of attempted murder first degree, and
related conspiracy and criminal solicitation charges.  She was committed to prison
in default of one million dollars bail.
On March 5, Foley again contacted the federal agent to relate that MacDonald
had learned of the arrest of Markward and his wife, and according to Foley, wanted
to pursue other arrangements to harm Smith.  That same day MacDonald was
arrested on the new charges and, according to the officer who arrested him, agreed
to “tell the real story,” i.e., to confess to the Spencer murder, and certain of the new
charges in exchange for leniency for his family.  The prosecutors then contacted
MacDonald’s defense attorney and, under circumstances not entirely clear, conferred
with the trial judge before whom MacDonald’s sentencing was pending to advise the
judge of MacDonald’s post-trial activities.1
1(...continued)
now arrested and that the hit man has been arrested, he still wants this done.
I am very concerned and I believe Jeff shares that concern that we need to
request the Court to put Glenn MacDonald or to order the prison, I guess, to put
Glenn MacDonald in a situation where he does not have access to a telephone, to
the mail, to other inmates to whom he can communicate these types of
solicitations.
* * * *  
[Defense Counsel]: I guess what you’re saying, you’re asking the judge to
put him in solitary confinement....
6
In response to the State’s request, the trial judge commented: “I think I’d like
to have him shipped off to maximum.  How do I go about doing that?  Do they have
pre-sentence in max?”  In response, MacDonald’s own counsel offered his view:
“Let me make this suggestion.  I don’t think you even need to do it because if he’s
committing crimes over the telephone, he’s violating the internal rules of the prison,
and they can send him down to solitary on their own initiative.”  The trial judge
commented, “I think I’d like to have him shipped off to maximum” but declined to
order MacDonald’s transfer in the absence of the necessary documentation.  The trial
judge encouraged the prosecutors to arrange the transfer to isolation, noting that the
Warden of the prison was “a reasonable person.”  With the apparent agreement of
MacDonald’s counsel and the State, the trial judge ordered MacDonald’s sentencing
2Apparently, under a “suicide watch,” an inmate is checked for physical movements by
a correctional officer every 20 minutes and his cell is illuminated at all times.  A concrete pad
serves as the bed, except when a mattress is permitted at night.  All meals are taken in the cell and
the prisoner is permitted no access to other inmates or the outside world.
7
to be moved up from the originally scheduled date of May 7 to March 11, six days
hence.  
On the eve of March 5, MacDonald was taken before a Justice of the Peace
for his initial appearance on the new charges.  Although one of MacDonald’s defense
counsel appeared with him before the Justice of the Peace Court located at the
Gander Hill Prison, he declined to discuss the charges with MacDonald, indicating
that he would visit MacDonald at a later time.
After his initial appearance before the Justice of the Peace, MacDonald was
immediately transferred from Gander Hill to the Delaware Correctional Center in
Smyrna.  Upon his arrival there, MacDonald was stripped to his underwear and
placed in an isolation cell, measuring 5 feet by 9 feet, and advised that he was being
placed on a “suicide watch”2 at the request of his counsel.  MacDonald remained in
isolation until the next visit from his defense counsel on March 9.
After four days of solitary confinement, during which time he had little sleep
and no communication with his family or counsel, MacDonald was transported to an
interview with his counsel at the maximum security portion of the prison.  Following
8
his stay in what is pejoratively referred to as the “hole”, McDonald was, in the
words of one of his attorney’s, “not a pretty sight.”  According to MacDonald, his
counsel informed him that they had requested the “suicide watch” because he
seemed “unstable.”
At the outset, his attorneys told him that there had been new developments in
his case.  Counsel vaguely reported to MacDonald that the police had wiretap
recordings, his wife had been arrested, other members of his family were going to
be arrested, and new charges against him were forthcoming  —  including the
attempt to murder Smith.  During this meeting, which lasted approximately 1 ½ to
2 hours, and without prior notice to MacDonald, his attorneys presented to him a
non-negotiable plea offer from the State.  MacDonald’s counsel outlined the terms
of the offer and stated that there was no time to “hem or haw” in deciding whether
to accept.  Specifically, the non-negotiable plea offer required that MacDonald: 
(1)
enter pleas of guilty to two new charges arising out of the
alleged conspiracy to harm Smith — criminal solicitation first degree
and conspiracy first degree; 
(2)
provide a videotaped confession of his guilt in the Spencer
killing; and,
3Both of MacDonald’s counsel testified that there was at least one claim of error arising
out of the murder trial that  was a strong basis for appeal.  One of MacDonald’s lawyers testified
that he told MacDonald:  “I believe we have a better than even shot of winning on the Doyle
issue, the issue is a very strong issue yes.”  
4Although the State’s offer was not reduced to writing, MacDonald’s counsel testified that
MacDonald received no direct benefit from the “take it or leave it” plea offer:
Q.
He was not exposed, at that point in time, to any penalties harsher
than the rest of his life in jail without probation or parole.
It wasn’t like that was a compromise on the State’s part, was it?
A.
Yeah, to the extent that they weren’t giving him anything on that.  That’s
absolutely correct.
Q.
So he gained nothing personally from a legal sense, from a legal point of
view.
A.
It’s all relative perhaps to what he thinks he gained by getting Tracy out
and the other discussions involving his family.  To him personally?
Q.
Yes, Glenn MacDonald’s legal self-interest was not served by this plea.
A.
His legal self-interest in my mind does include the other co-defendants.
That occurs in any kind of case where you have co-defendants.
To his situation as to what sentence he was going to be serving, he got no
benefit from, that’s correct.  
9
(3)
waive all rights to appeal or to seek postconviction relief
with respect to his murder conviction.3
For its part, the State apparently agreed to give preferential treatment to
MacDonald’s wife and parents in connection with the “new” charges.4  MacDonald
stated that his counsel informed him that there were no defenses to the new charges
10
and that he would be required to “relinquish my appeal rights” in the original
murder conviction.  Despite his initial rejection of the plea offer, MacDonald
eventually agreed to its terms.  A prison guard testified that when MacDonald left
the meeting with his counsel he was “kind of upset and may have been crying.”  
Later that day, MacDonald’s counsel wrote a five page letter to the
prosecution in which they related “the events surrounding the Julie Spencer homicide
and recent events involving Mr. MacDonald’s wife and Garret Markward” based on
counsels’ meeting earlier that day with MacDonald.  The letter related MacDonald’s
detailed admission to the killing of Julie Spencer; his involvement in efforts to kill
or intimidate Smith; the possible involvement of his wife in the new charges; and,
his denial that he had ever spoken to his father about the Smith matter.  The letter
recites that the information contained therein “shall be considered privileged
pursuant to the attorney-client relationship and shall remain confidential” but could
be disclosed to the Delaware State Police “for the purpose of assisting in the
interview of Mr. MacDonald in connection with these events.”
That evening, in preparation for a recorded confession, MacDonald reviewed
a written outline of the Spencer killing that was prepared by his counsel, and which
11
was consistent with the State’s case against him.  The following day, March 10,
MacDonald was taken to a State Police station to give a videotaped statement.  Prior
to the arrival of his counsel, MacDonald was permitted to call his parents.  In that
conversation, later related by a witness who testified at the Rule 61 hearing,
MacDonald claimed that he had been threatened with the arrest of his father and that
he was going to give a confession that had been essentially written for him.
MacDonald’s statement to the police, given in the presence of his counsel and
the prosecutor, acknowledged his guilt in the killing of Spencer and his involvement
in the plot against Allan Smith.  At the beginning of his statement, MacDonald made
clear that his concern was for his parents and that they would secure lenient
treatment in exchange for his statements and guilty pleas.  MacDonald requested an
acknowledgment from the prosecutor that “my father wouldn’t be arrested.”  The
prosecutor responded:
(Prosecutor):  At, at this point we have no reasons to believe
your father’s involved.  And obviously, down the line if some, for some
reason evidence develops that your Dad’s involved, and, you know,
you’re the one that’s telling us today.  If he’s involved tell us today.
He’ll be taken care of the same way Mom is.  Ah, down the line if it
develops it would be the same scenario with Dad.
12
(emphasis supplied).  Later, in the same interview, a State Police questioner again
raised the specter of family involvement when he prefaced his questioning of
MacDonald with the following statement:  
Okay.  And I know Tracy is in a jam.  And your mother’s in a jam,
and, ah, possibly your fath...
The day after he gave his videotaped statement, MacDonald appeared before
the trial judge and pleaded guilty to conspiracy to commit murder and solicitation
arising out of the Smith matter.  The written plea agreement also recited that
“Defendant agrees not to pursue an appeal or postconviction relief from his
conviction for First Degree Murder.”  The trial judge engaged in a colloquy with
MacDonald in which MacDonald acknowledged his guilt and that he was entering
into the plea agreement voluntarily and knowingly, and that he was satisfied with the
representation of counsel.  One of MacDonald’s counsel advised the court that “the
resolution of this matter came swiftly and suddenly in terms of tying a complete
package up . . . that Glenn MacDonald came to decide that for once in his life, he
had the opportunity to do the smart thing, and the right thing and tell the truth.”
Following acceptance of his plea, MacDonald was sentenced to life
imprisonment on the murder conviction and two consecutive five year terms on the
new charges.  In imposing the sentence, the trial judge commented: “In my sentence,
13
it shall be you who will symbolically disappear into the cold, stark confines of a
penal institution where, ultimately you shall die.”
In 1996, almost three years after his sentencing, MacDonald, with new
counsel, filed a motion to withdraw his guilty plea based on several grounds — 
including ineffective assistance of counsel.  The trial judge recused himself and the
motion was assigned to another Superior Court judge.  The successor judge
conducted a lengthy evidentiary hearing at which several witnesses testified,
including MacDonald, his counsel, and the prosecutor.  In a post-hearing decision,
the Superior Court rejected MacDonald’s claim that his guilty plea was involuntary
or that he had been denied effective assistance of counsel.  While acknowledging that
the conditions of MacDonald’s confinement preceding his meeting with counsel on
March 9 “were less than ideal,” the judge concluded that those conditions did not
interfere with “his ability to make knowing and voluntary decisions concerning the
situation he was facing.”  With respect to the claims of ineffective assistance of
counsel, the court concluded that MacDonald “had his mind made up before
consulting them and they simply reaffirmed his intentions.”  The court further
concluded that, given the nature of the State’s “take it or leave it” plea offer,
MacDonald’s counsel had little time to investigate the new charges and advise
14
MacDonald concerning possible defenses and, thus, their representation was not
deficient under the circumstances.
II
Our review of an appeal from the Superior Court’s denial of a motion to
withdraw a guilty plea is one of abuse of discretion.  See Blackwell v. State, Del.
Supr., 736 A.2d 971, 972 (1999).  To the extent that the effort to withdraw a guilty
plea is premised upon allegations of ineffectiveness of counsel, however, “we
carefully review the record to determine whether ‘competent evidence supports the
court’s findings of fact and whether its conclusions of law are not erroneous.’”
Outten v. State, Del. Supr., 720 A.2d 547, 551 (1998) (quoting Dawson v. State,
Del. Supr., 673 A.2d 1186, 1190 (1996)).
Preliminarily, the State argues that MacDonald’s claim fails procedurally
under Superior Court Rule 61(i)(3) because he did not file an appeal following his
guilty plea and thus must demonstrate cause for relief and actual prejudice.  This
contention was not raised in the Superior Court and ordinarily would not be
considered by this Court on review.  See Del. Supr. Ct. R. 8.  The principal and,
15
in our view, dispositive basis for relief advanced by MacDonald is posited upon a
claim of ineffective assistance of counsel, a ground not assertable on direct appeal
but appropriate in motions for postconviction relief.  See Flamer v. State, Del.
Supr., 585 A.2d 736, 753 (1990).  Thus, even if entertained on review, the
procedural bar advanced by the State is without merit.
III
Under the circumstances revealed in this record, the entry of the guilty pleas
by MacDonald is problematic in several respects.  The most troubling is the
atmosphere created by the combined efforts of the prosecutor and defense counsel,
with the acquiescence of the trial judge, in arranging for the transfer of the defendant
to isolation under a “suicide watch” where he was held for approximately four days.
Even if it is assumed that the prosecutor and the trial judge had reason to be
concerned about the investigation into MacDonald’s attempt to harm a witness, the
events which followed that revelation were extraordinary.  On March 5, 1993,
MacDonald was in prison pending a presentence investigation with sentencing
scheduled for May 7, 1993.  Within six days, four of which were spent in solitary
confinement, he had been arrested on new charges, confessed and pleaded guilty to
16
the charges of which he had been convicted in addition to the new charges,
surrendered his appeal and postconviction rights, and was sentenced to life
imprisonment plus ten years.
In denying MacDonald’s effort to withdraw his guilty plea, the Superior Court
concluded that the plea had been voluntarily entered after full opportunity to receive
the advice of counsel.  But given the highly unusual circumstances under which that
advice was given, the defendant’s subsequent wavier of his constitutional rights is
open to question.
A.
An attorney has an obligation to fully communicate to his or her client the
terms and conditions of proffered plea bargains in criminal cases.  See Prof. Cond.
R. 1.2; see also Prof. Cond. R. 1.4.  In this setting, attorneys are frequently called
upon to advise and consult with their clients in order to assist the client in
determining how best to proceed.  See Prof. Cond. R. 1.2; see also Prof. Cond. R.
2.1.  An attorney’s role in this area of representation is critical and fulfilling that role
requires the attorney to act with diligence.  See Prof. Cond. R. 1.3. 
17
The American Bar Association has set forth standards that highlight the
responsibilities of defense counsel in connection with plea discussions and
agreements.  Standard 14-3.2 of the ABA Standards for Criminal Justice provides
that: 
(a)
Defense counsel should keep the defendant advised of
developments arising out of plea discussions conducted with the
prosecuting attorney, and should promptly communicate and explain
to the defendant all plea offers made by the prosecuting attorney.
(b)
To aid the defendant in reaching a decision, defense
counsel, after appropriate investigation, should advise the defendant
of the alternatives available and address considerations deemed
important by defense counsel or the defendant in reaching a decision.
Defense counsel should not recommend to a defendant acceptance of
a plea unless appropriate investigation and study of the case has been
completed.
ABA, STANDARDS FOR CRIMINAL JUSTICE, PLEAS OF GUILTY, Standard 14-3.2 (3d
ed. 1999)(emphasis supplied).  As the Standard makes clear, the role of defense
counsel in the negotiation of guilty pleas is critical.  While the decision to accept a
plea offer is personal to the defendant, that decision must be an informed one, to be
made only after full consultation with counsel.  Defense counsel is expected to be
an advocate for his client in any adversary proceeding, but must function as a
counselor as well.  In the area of plea negotiations, the advice of counsel is vital and
that duty can be effectively discharged only after defense counsel has investigated
5Courts have looked askance at plea agreements that benefit third parties.  In Bordenkircher
v. Hayes, 434 U.S. 357, 363 n.8 (1978), the Supreme Court noted that “adverse or lenient
treatment for some person other than the accused ... might pose a greater danger of inducing a
false guilty plea by skewing the assessment of the risks defendant must consider.” Where threats
to prosecute third persons form part of plea negotiations there must be probable cause to support
the crimes contemplated to be charged and courts accepting a plea under such circumstances must
take special care to assure the voluntariness of such a plea.  See United States v. Nuckols, 5th Cir.,
606 F.2d 566, 570 (1979).
18
the basis for any plea offer.  Here, MacDonald’s counsel conducted no investigation
into the State’s new charges against their client, apart from an examination of the
probable cause sheet supporting MacDonald’s arrest.  In particular, counsel never
interviewed MacDonald’s parents (whose protection from prosecution was a
principal benefit MacDonald was to receive for the plea bargain) to determine
whether there was a basis for a viable prosecution against them.5 
While the State’s take it or leave it plea offer obviously created little room for
negotiation, the very nature of that offer required that counsel investigate fully the
basis for the State’s new charges and the prospect that the prosecution against
MacDonald’s parents was a negotiable matter.  In effect, MacDonald’s counsel
accepted the State’s case at face value and permitted their client to surrender a
meritorious appeal claim and the entitlement to postconviction relief for a benefit
which was, at best, vague and indefinite.  Even the State concedes that it had no
real basis for prosecuting MacDonald’s father (although it equivocated on this point
19
in securing MacDonald’s statement) and no direct evidence that MacDonald’s
mother was involved in the conspiracy against Smith.
B.
Apart from the lack of sufficient investigation, we are quite troubled by
defense counsel’s participation in, even encouragement of, the efforts of the State
and the trial judge to change the conditions of their client’s incarceration.  The
record of the office conference between the trial judge, the prosecution, and defense
counsel that occurred on March 5, 1993, without MacDonald’s knowledge, is
remarkable in several respects.  The conference occurred at a time when
MacDonald was awaiting a presentence investigation and there were no other
matters relating to his murder conviction before the court.  The conference was
requested by the prosecution to advise the trial judge of the “new information” it
had uncovered concerning MacDonald’s effort to eliminate or intimidate a witness
in his previous trial.  As the prosecutor made clear in that conference, “we are not
totally finished investigating as of this moment.”  Despite these tentative results,
however, the State proceeded to describe MacDonald’s conduct to the judge who
6While we express no definitive opinion on the matter, we are troubled by the trial judge’s
receipt of information adverse to the interests of a defendant pending sentencing, even in the
presence of defense counsel.  It is also a matter of concern that the trial judge accepted the
defendant’s plea after participating in arrangements to impose severe conditions of confinement
during plea negotiations and after becoming enmeshed in the investigative stage of the second set
of charges.  Wisely, the trial judge recused himself from participating in the Rule 61 proceedings
in which the defendant sought to withdraw his guilty pleas.
20
would have the responsibility to sentence him, and before whom the guilty pleas
were ultimately entered.6  To add to these unusual circumstances, defense counsel,
who had conducted no investigation of the new charges and made no objection to
the prosecution’s relating to the trial judge investigative information adverse to their
client,  acquiesced in a plan to have their client placed in isolation.  Given the effect
of these conditions on the defendant over four days, they assisted in creating an
onerous climate in which their client could not intelligently evaluate the State’s plea
offer.  Defense counsel’s consent to the extreme conditions of their client’s
confinement can hardly be viewed as serving MacDonald’s best interests.
C.
A third factor that suggests counsel did not effectively serve their client’s
interests is the terms of the plea agreement itself.  As previously noted, counsel
permitted their client to surrender a claim of error that they believed provided a
strong basis for overturning MacDonald’s conviction on appeal.  More importantly,
21
defense counsel permitted MacDonald to surrender his right to postconviction relief,
which presumably included the right to claim ineffective assistance of counsel in the
events leading up to his sentencing.  Under these circumstances defense counsel
were, in effect, insulating themselves from a claim that they rendered deficient
service to their client and thus created a conflict of interest. 
As an initial matter, this Court has never directly opined on whether, as a
component of plea negotiations, a defendant may waive the right to appeal or seek
postconviction relief.  Most states have held that there is no bar to waiver of appeal
rights as part of a plea agreement.  In Maryland, for example, waiver of the right to
appeal a criminal conviction is permitted so long as it is knowing and voluntary.  See
Cubbage v. State, Md. Ct. App., 498 A.2d 632 (1985); see also, e.g., Brown v.
Haynes, W.D. Mo., 385 F. Supp. 285 (1974); Gwin v. State, Ala. Crim. App., 456
So.2d 845 (1984); Staton v. Warden, Conn.Supr., 398 A.2d 1176 (1978); People v.
Fearing, Ill. App., 442 N.E.2d 939 (1982); Majors v. State, Ind. App., 568 N.E.2d
1065 (1991); State v. Hinners, Iowa Supr., 471 N.W.2d 841 (1991); State v.
Gibson, N.J. Supr., 348 A.2d 769 (1975); Blackburn v. State, W. Va. Supr., 290
S.E.2d 22 (1982).  The rationale for permitting waiver of appeal rights is that
because a defendant may waive significant constitutional rights —  including trial by
22
jury and the right to counsel — a defendant may also waive the right to appeal,
provided the waiver is knowing, intelligent and voluntary.  See Cubbage, 498 A.2d
at 638; see also United States v. Rutan, 8th Cir., 956 F.2d 827, 829-30 (1992). 
Courts permitting the waiver of a defendant’s right to seek postconviction relief have
applied this same analysis.  See, e.g., Watson v. United States, 6th Cir., 165 F.3d
486, 488-89 (1999); United States v. Wilkes, 5th Cir., 20 F.3d 651, 653 (1994).  To
the contrary, Michigan and Arizona have adopted the per se rule that the right to
appeal may not be waived as part of a plea agreement, reasoning generally that, as
a matter of policy, the right to appeal is so vital for the protection of other rights that
it should not be negotiable.  See People v. Butler, Mich. App. Ct., 204 N.W.2d 325
(1972); see also State v. Ethington, Ariz. Supr., 592 P.2d 768 (1979)(stating that
public policy forbids “a prosecutor from insulating himself from review by
bargaining away a defendant’s appeal rights”).  It is unnecessary, however, to decide
in this case the contours of a waiver of appeal rights incident to plea negotiations.
The critical issue before us is whether the waiver of MacDonald’s right to appeal or
7Interestingly, the State did not challenge MacDonald’s Rule 61 motion for postconviction
relief on the ground that he effectively waived his right to seek postconviction relief under the
terms of the plea agreement.
23
seek postconviction relief,7 even if permissible, was the result of ineffective
assistance of counsel, thereby rendering his plea invalid.  
24
IV
A criminal defendant’s decision to plead guilty involves the waiver of several
important constitutional rights.  Therefore, in order for a guilty plea to be valid as
a matter of due process, an agreement waiving these rights must be entered into
knowingly, intelligently, and voluntarily.  A defendant’s plea agreement containing
a wavier of the right to appeal or seek postconviction relief does not surrender the
defendant’s right to argue that the decision to enter into the plea was not knowing
and voluntary because it was the result of ineffective assistance of counsel.   See
DeRoo v. United States, 8th Cir., 223 F.3d 919, 923-24 (2000).  Indeed, “[c]laims
of ineffective assistance of counsel … challenge the voluntary and intelligent nature
of the plea agreement.”  United States v. Ruiz, 9th Cir., 241 F.3d 1157, 1165
(2001).  As one court has commented: “[j]ustice dictates that a claim of ineffective
assistance of counsel in connection with the negotiation of [an] agreement cannot be
barred by the agreement itself – the very product of the alleged ineffectiveness.”
Jones v. United States, 7th Cir., 167 F.3d 1142, 1145 (1999).
Most federal courts permit the waiver of the right to appeal or seek
postconviction relief in a plea agreement except when the waiver would bar a claim
that the guilty plea was the result of ineffective assistance of counsel.  See, e.g.,
25
United States v. Black, 10th Cir., 201 F.3d 1296, 1301 (2000); Jones, 167 F.3d at
1145; DeRoo, 223 F.3d at 923-24; United States v. Henderson, 5th Cir., 72 F.3d
463, 465 (1995).  To determine whether an appeal for postconviction relief
withstands a waiver in a plea agreement based on a claim of ineffective assistance
of counsel, the Tenth Circuit applies a test based on the Supreme Court decision in
United States v. Broce, 488 U.S. 563 (1989), which requires a guilty plea to be both
voluntary and counseled.  See United States v. Cockerham, 10th Cir., 237 F.3d
1179, 1187 (2001).  Pursuant to this two-pronged test, it must be determined: (i)
“whether there is any basis for a claim of ineffective assistance of counsel,” and (ii)
“whether that ineffectiveness claim pertains to the validity of the plea.”  Cockerham,
237 F.3d at 1187.
The oft-stated test for evaluating the effectiveness of counsel requires the
Court to engage in a two-pronged analysis: (i) whether “counsel’s representation fell
below an objective standard of reasonableness” and (ii) whether “there is a
reasonable probability that, but for counsel’s unprofessional errors, the result of the
proceeding would have been different.”  Strickland v. Washington, 466 U.S. 668,
694 (1984); see also Riley v. State, Del. Supr., 585 A.2d 719, 726 (1990).  The
burden of proving ineffective assistance of counsel is on the party asserting it.
26
Where the claim arises in the context of a guilty plea, the defendant must show that
“there is a reasonable probability that, but for counsel’s errors, he would not have
pleaded guilty and would have insisted on going to trial.”  Hill v. Lockhart, 474
U.S. 52, 59 (1985); see also Albury v. State, Del. Supr., 551 A.2d 53, 58 (1988).
The State argues, as the Superior Court concluded in denying MacDonald’s
motion to withdraw his guilty plea, that the plea agreement was the result of
MacDonald’s insistence.  In short, the State contends that the decision was
MacDonald’s, not his counsel’s.  This argument overlooks the vital role played by
defense counsel in advising a client with respect to the entry of a guilty plea.  We
believe, consistent with the ABA standards, that the right to counsel includes the
right to informed advice after “appropriate investigation.”  ABA, STANDARDS FOR
CRIMINAL JUSTICE, Standard 14-3.2.  In Strickland, the Supreme Court noted that
the ABA Standards for Criminal Justice (“The Defense Function”) are guides or
norms of practice for determining whether counsel’s assistance was reasonable.
Strickland, 466 U.S. at 688.  In applying the reasonableness or competence prong,
“the court should keep in mind that counsel’s function, as elaborated in prevailing
professional norms, is to make the adversarial testing process work in the particular
case.”  Id. at 690.  On the record, we reluctantly conclude that MacDonald’s counsel
8The hasty arrangements for MacDonald’s guilty plea and the acceleration of his sentencing
(continued...)
27
did not provide the required adversarial testing of the State’s efforts to have
MacDonald abandon his appellate rights and plead guilty to new charges.
In this case, prior to meeting with their client, MacDonald’s counsel failed to
fully investigate the allegations against their client.   MacDonald’s counsel did not
question the State’s informant, MacDonald’s wife, or his parents.  Indeed, it appears
that his attorneys did not even seek an explanation from MacDonald as to what had
transpired.  Counsel merely stated that MacDonald had no defenses to the current
charges.  One of his attorneys even admitted that he “did not offer [MacDonald]
professional advice as to whether he should accept the plea offer.”  MacDonald’s
counsel only made clear that he had no choice other than to accept  the State’s offer,
without modification, or reject it outright. There were no plea negotiations in this
case and no effort was made to negotiate a more favorable plea with the State.
Given the conditions of the defendant’s confinement, which, were in effect with his
counsel’s acquiescence, the lack of investigation, the surrender of viable appeal and
postconviction remedies, the acceleration of the sentencing process and the lack of
direct benefit secured in the plea agreement, we conclude that the defendant’s plea
of guilty was not the product of the competent advice of counsel.8 In the absence of
8(...continued)
also placed him at a significant procedural disadvantage.  Under Superior Court Criminal Rule
32(d), a motion to withdraw a guilty plea after sentencing will be granted only to correct
“manifest injustice”  — a higher standard than would have resulted had MacDonald reconsidered
his plea agreement before his previously scheduled date for sentencing — May 7, 1993.
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such advice, the plea agreement lacks the necessary elements of intelligence and
voluntariness and cannot withstand collateral attack. 
Our invalidation of the defendant’s guilty plea on the basis of ineffective
assistance of counsel is not intended as a reflection of the general professional
standing of his trial counsel — both of whom are seasoned criminal law practitioners
who have rendered able assistance to their clients in many cases in the Superior
Court and in this Court.  Unfortunately, in this highly unusual case, counsel
permitted themselves to become allies with the prosecution in an effort to prevent
their own client from committing further offenses and, thereafter, were persuaded
that MacDonald’s best interests lay in speedily resolving all the charges — both those
awaiting sentencing and those not indicted — pending against their client.  But, by
any objective standard, permitting a client to enter into an onerous plea agreement
under adverse conditions of confinement without appropriate investigation cannot be
viewed within the range of effective assistance of counsel.
As previously noted, objectively considered, the services rendered by
MacDonald’s counsel, from the time of his arrest on the new charges to the entry of
29
his guilty plea, clearly fell below the standard expected of competent defense
counsel.  Permitting their client to give up viable appeal rights, postconviction
remedies, and plead to new charges in an atmosphere of haste and coercion without
proper investigation was objectively unreasonable.  The record in this case also
supports the defendant’s claim that, had he received proper advice and assistance
from counsel, he would not have surrendered trial and appellate rights in exchange
for State promises that were of no direct benefit to him.  Thus, we are satisfied that
ineffective assistance of counsel has been demonstrated on this record.
We conclude that the plea agreement entered into by the defendant and the
guilty pleas that followed must be set aside as not voluntary and intelligently entered
because of the ineffective assistance of counsel.  Accordingly, the decision of the
Superior Court is REVERSED.  Implicit in our ruling invalidating MacDonald’s
guilty pleas is the requirement that he be resentenced on the murder conviction.  This
will ensure his entitlement to file a timely appeal.  See Braxton v. State, Del. Supr.,
479 A.2d 831 (1984). Our ruling does not affect the convictions for which the
defendant was awaiting sentence nor does it affect the prosecution for any subsequent
offenses which were pending at the time of the entry of the guilty pleas now
30
invalidated.  This matter is REMANDED for further proceedings consistent with this
decision.