In the

United States Court of Appeals

For the Seventh Circuit ____________________

No. 17-2263

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

ULISES DE LA CRUZ,

Defendant-Appellant.

____________________

Appeal from the United States District Court for the

Northern District of Illinois, Eastern Division.

No. 16 CR 462-4 — Rebecca R. Pallmeyer, Judge.

____________________

ARGUED FEBRUARY 23, 2018 — DECIDED JULY 30, 2018

____________________

Before FLAUM, SYKES, and HAMILTON, Circuit Judges.

HAMILTON, Circuit Judge. From the time he was a young 

adolescent, defendant Ulises De La Cruz was a member of the 

Latin Kings gang. De La Cruz was one of many Latin Kings 

swept up in a federal prosecution charging the gang with operating a racketeering conspiracy in the Chicago area. He 

pleaded guilty to the conspiracy charge and argued at sentencing that the district judge should reduce his sentence by 

the amount of time he had already served in prison on charges 
2 No. 17-2263

related to conduct that was part of the ongoing racketeering 

conspiracy. He was partially successful. The district judge, in 

recognition of a prison sentence De La Cruz was still serving, 

imposed a 210-month sentence. That term was the bottom of 

the range recommended by the U.S. Sentencing Guidelines. 

De La Cruz appeals this sentence. He contends that the 

Guidelines entitle him to a greater reduction due to another 

prior prison sentence he served in full. His argument misreads the discretionary nature of the Guidelines relating to 

downward departures for discharged prison sentences. The 

district judge did not abuse that discretion, so we affirm.

In January 2016, a grand jury indicted De La Cruz and 

fourteen other members of the Latin Kings for participating 

in a racketeering conspiracy in violation of 18 U.S.C. 

§ 1962(d). De La Cruz pleaded guilty to the racketeering 

charge, preserving his right to appeal the sentence. At no time 

did he dispute the factual allegations in the presentence investigation report prepared by the U.S. Probation Office. That 

report provides the facts summarized below that detail his 

role in the Latin Kings and the many factors relevant to his 

sentence. 

De La Cruz joined the Latin Kings in 1999 when he was 

not yet a teenager. He rose through the ranks of the Maywood, 

Illinois section of the gang, becoming the Chief Enforcer of 

that unit by 2008 and eventually its second in command, or 

Cacique. In this leadership role, De La Cruz inflicted physical 

punishment on members of the gang who violated its rules 

and the orders of its leadership. For example, on one occasion 

in 2013, De La Cruz participated in a meeting where his section beat a member for accusing another member of cooperating with law enforcement without sufficient evidence. The 
No. 17-2263 3

beating victim suffered severe injuries that required medical 

care. At that same meeting, De La Cruz ordered others to 

shoot rival gang members and former Latin Kings, threatening beatings if they failed to comply. 

During his time as a Latin King, De La Cruz racked up ten 

convictions and more arrests for a variety of offenses. His convictions ranged from criminal damage to property and cannabis possession to aggravated unlawful use of a weapon and 

aggravated discharge of a firearm. Several of these convictions might count as part of the underlying racketeering conduct, but because De La Cruz was convicted of these offenses 

“prior to the last overt act” in furtherance of the racketeering 

conspiracy, the Guidelines treat these offenses as part of the 

defendant’s criminal history. See U.S.S.G. § 2E1.1 cmt. 4. Only 

the two weapons offenses from 2008 and 2014 are relevant to 

this appeal.

In November 2008, police responded to a report of shots 

fired. Officers saw De La Cruz toss a semi-automatic handgun 

out of a vehicle that fled the scene. De La Cruz was convicted 

of violating an Illinois statute for the aggravated unlawful use 

of a weapon and sentenced to two years in prison. He served 

his prison sentence and, with credit for good behavior in 

prison, was released on parole in July 2009. The case was 

closed the following year.1

 

1 After De La Cruz’s case was closed, this court and the Illinois Supreme Court invalidated that statute as contrary to the Second Amendment. See Moore v. Madigan, 702 F.3d 933, 942 (7th Cir. 2012), rehearing en 

banc denied, 708 F.3d 901 (7th Cir. 2013); People v. Aguilar, 2 N.E.3d 321, 328 

(Ill. 2013). Because of the statute’s invalidation, De La Cruz received no 

criminal history points for this conviction in his federal sentencing for the 

racketeering conspiracy.
4 No. 17-2263

In March 2014, De La Cruz fired two shots into a secondfloor window of a rival gang member’s residence and four 

shots into a car outside the residence. He was arrested, incarcerated, and convicted of aggravated discharge of a firearm. 

The state court sentenced him to five years in prison for the 

offense. From the time of his indictment in this federal case 

through his federal sentencing, De La Cruz remained in 

prison for the 2014 offense. The probation officer believed that 

this offense was likely part of the underlying racketeering activity. Because telephone recordings showed that De La Cruz 

continued to act in furtherance of the conspiracy while in 

prison on this charge, the probation officer counted this offense toward his criminal history score and not toward the 

score for his underlying offense in accordance with the Guidelines. See U.S.S.G. § 2E1.1 cmt. 4.

Several recorded statements supported the conclusion 

that De La Cruz continued to participate in the conspiracy. For 

example, in December 2014, he told another gang member 

while in jail that he “put his freedom off” for the gang and 

was “in it for the long run.” In January 2015, he said that once 

released from jail, he would be “right back like I never left.” 

More ominously, De La Cruz responded to news that his fellow members had shot and severely injured a former member 

by expressing approval. He said that if the victim wound up 

in jail, that would be “the worst thing for him.” On another 

occasion, he said that if allegations that some Latin Kings in 

custody were cooperating with law enforcement were true, he 

would have those persons attacked or killed.

At sentencing, De La Cruz argued that he should receive 

credit for time served in Illinois prisons for crimes he committed in furtherance of the Latin Kings criminal conspiracy. The 
No. 17-2263 5

main justification for his proposed adjustment centered on the 

inequity of De La Cruz serving more time than his codefendants in the case who previously escaped prison terms, despite 

ongoing participation in the scheme. After all, De La Cruz 

claimed, he was already serving time in Illinois prison for a 

charge related to the federal conspiracy when he was indicted 

in this federal case.

The U.S. Probation Office calculated De La Cruz’s sentencing range as 210 to 240 months using the 2016 Guidelines 

Manual. The district judge said that she was “sensitive to the 

fact that” De La Cruz “has already served significant time on 

another offense in state court.” To account for this fact and to 

avoid the “need to subtract or add anything to make this [sentence] work,” the judge imposed a sentence at the bottom of 

the guideline range, 210 months, and ordered that it be served 

concurrently with the remainder of De La Cruz’s state sentence.

On appeal, De La Cruz argues that the district judge committed procedural error by failing to give him more credit toward his federal sentence for time served in state prison for 

offenses that formed part of the underlying racketeering activity. We review de novo claims of procedural errors in sentencing, such as a district court’s interpretations of the Guidelines. United States v. Hoffman, 847 F.3d 878, 881 (7th Cir. 2017). 

We review the district court’s substantive sentencing determinations for abuse of discretion. Gall v. United States, 552 U.S. 

38, 41 (2007). De La Cruz’s arguments on appeal focus largely

on specific Guidelines that are explicitly discretionary, so we 

consider whether the district judge abused that discretion.
6 No. 17-2263

The Guidelines provide detailed and complex directions 

for determining their advice. The Guidelines also include application notes that attempt to remove ambiguity or confusion 

that might arise in applying a specific guideline to the facts in 

a specific case. The 2016 Guidelines devote 572 pages to this 

goal, not counting appendices and introductory materials. 

Despite these painstaking efforts to promote more uniform 

sentencing by guiding sentencing judges’ discretion, some 

Guidelines and application notes recognize that particular 

cases require judges to just use their—wait for it!—judgment. 

Cf. Kate Stith and Jose A. Cabranes, Fear of Judging (1998) 

(criticizing mandatory federal Sentencing Guidelines for often preventing exercise of judgment in sentencing).

Racketeering offenses such as De La Cruz’s are complicated and trigger these highly discretionary Guidelines. Racketeering conspiracies involve long-term, ongoing criminal enterprises in which individual conspirators may commit many 

individual crimes. The Racketeer Influenced Corrupt Organizations Act, 18 U.S.C. § 1961 et seq., was intended to give 

prosecutors powerful new tools to go after organized crime, 

where the ongoing, organized nature of the crimes added to 

the harm to society, beyond the harm caused by the individual 

crimes. Particularly successful racketeering organizations like 

the Latin Kings succeed in part because of their ability to keep 

members loyal and committed to criminal activity despite 

prison sentences.

In a racketeering case, the sentencing judge must determine how to punish a person based on his participation in an 

ongoing criminal enterprise when he has already been punished for ingredients that form the enterprise. The Guidelines 
No. 17-2263 7

recognize the difficult and individualized nature of this inquiry. In some cases, the defendant’s continued criminal activity might reasonably be deemed an aggravating factor, calling for a stiffer sentence. In others, earlier sentences imposed 

by other courts might reasonably be deemed a mitigating factor. The Guidelines provide sentencing judges wide latitude 

to give defendants some credit for time served, or not.

On appeal, De La Cruz has sharpened considerably the argument he made in the district court. He challenges only one 

determination of the district judge. According to De La Cruz, 

the judge erred by not discounting his sentence by the time he 

served for his 2008 aggravated unlawful use of a weapon. He 

claims this decision lay outside the district judge’s discretion 

because the Guidelines make this discount mandatory. He 

identifies this mandate in U.S.S.G. § 5G1.3(b). It provides that 

when a defendant received a prison sentence for an “offense 

that is relevant conduct to the instant offense of conviction,” 

the sentencing “court shall adjust the sentence for any period 

of imprisonment already served on the undischarged term of 

imprisonment,” U.S.S.G. § 5G1.3(b)(1), and “the sentence for 

the instant offense shall be imposed to run concurrently to the 

remainder of the undischarged term of imprisonment,” 

U.S.S.G. § 5G1.3(b)(2).

De La Cruz’s 2008 weapon offense was an “offense that is 

relevant conduct to the instant offense” of racketeering, but 

§ 5G1.3(b) does not apply to that conviction because no portion of that sentence remained “undischarged” at the time of 

sentencing, as that provision requires. United States v. Pietkiewicz, 712 F.3d 1057, 1060 (7th Cir. 2013); United States v. Blackwell, 49 F.3d 1232, 1241 (7th Cir. 1995). As the presentence investigation report makes plain, Illinois released De La Cruz 
8 No. 17-2263

on parole in July 2009 and closed that weapons case in July 

2010. De La Cruz’s prison term was not “undischarged” when 

he shot into the car and apartment of a rival gang member in 

March 2014 or committed any of the other four crimes detailed in the report between his release from prison in 2009 

and his return to custody in 2014. De La Cruz also relies on 

Application Note 4 to § 5G1.3, but that note also applies only 

to an “undischarged term of imprisonment.” U.S.S.G. 

§ 5G1.3(d) & cmt. 4. Those provisions simply did not apply 

because, at the time of his federal sentencing, De La Cruz had 

completed his sentence for the 2008 offense. 

It appears, however, De La Cruz’s counsel cited an older 

version of the Guidelines Manual not used in this case and 

probably meant instead to cite Application Note 5 to § 5G1.3. 

In previous editions of the Guidelines Manual, Application 

Note 5—which refers to discharged prison terms—appeared 

as Application Note 4. See U.S.S.G. § 5G1.3 cmt. 4 (2013). 

What is now Application Note 5 makes clear that the judge’s 

treatment of already-discharged prison terms is discretionary. 

Note 5 advises that in “the case of a discharged term of imprisonment, a downward departure is not prohibited” in certain circumstances. U.S.S.G. § 5G1.3 cmt. 5 (2016) (emphasis 

added). This note operates essentially as a cross-reference to 

§ 5K2.23, which applies to already-discharged sentences. By 

guiding the sentencing court to “See §5K2.23,” the note advises that the Guidelines do not compel sentencing judges to 

ignore a defendant’s discharged prison terms if § 5K2.23 applies. Id. We now turn to that provision. 

As we read his brief, De La Cruz also constructed an argument around § 5K2.23. Unlike § 5G1.3(b), which applies only 

to undischarged sentences, § 5K2.23 provides the district 
No. 17-2263 9

court with discretion to adjust a defendant’s sentence downward for discharged sentences. Also, unlike the mandatory 

credit required by § 5G1.3(b)—though the notion of a mandatory term in the advisory Guidelines requires a little extra intellectual flexibility—any adjustment under § 5K2.23 is entirely discretionary. Employing a belt-and-suspenders approach, that provision makes clear in its opening clause and 

concluding sentence that any adjustment for discharged sentences is up to the sound discretion of the district court: 

A downward departure may be appropriate if the 

defendant (1) has completed serving a term of 

imprisonment; and (2) subsection (b) of §5G1.3 

... would have provided an adjustment had that 

completed term of imprisonment been undischarged at the time of sentencing for the instant 

offense. Any such departure should be fashioned 

to achieve a reasonable punishment for the instant 

offense.

U.S.S.G. § 5K2.23 (emphases added). De La Cruz has not explained why the district judge’s decision not to apply § 5K2.23 

was an abuse of her discretion, and we find no abuse of discretion here.

As a final matter, De La Cruz asserts that the district judge 

“did not address” the 2008 weapons offense at sentencing. We 

have said that “whenever a district judge is required to make 

a discretionary ruling that is subject to appellate review, we 

have to satisfy ourselves ... that [s]he exercised [her] discretion, that is, that [s]he considered the factors relevant to that 

exercise.” United States v. Cunningham, 429 F.3d 673, 679 (7th 

Cir. 2005), citing Carr v. O’Leary, 167 F.3d 1124, 1127 (7th Cir. 

1999), and additional cases. The problem with De La Cruz’s 
10 No. 17-2263

argument is that when arguing before the district judge for 

downward adjustments, he bundled together his 2008 and 

2014 offenses. In his sentencing memorandum, he added up 

all the time he served on his multiple convictions related to 

his federal racketeering charge and asked for a reduction of 

more than five years. He also failed to cite § 5K2.23 or any 

Guideline in his sentencing memorandum when arguing for 

an adjustment. At the sentencing hearing, De La Cruz’s attorney again combined these separate offenses in his oral argument. Since he presented these convictions as one issue at sentencing, the district court surely did not err by treating his 

prior offenses the same way and focusing on the 2014 conviction.

The judgment of the district court is

AFFIRMED.