In the 

United States Court of Appeals 

For the Seventh Circuit ____________________ 

Nos. 19-2174, 19-2185 & 19-2186 

UNITED STATES OF AMERICA, 

Plaintiff-Appellant, 

v.

ADEL DAOUD, 

Defendant-Appellee. 

____________________ 

Appeals from the United States District Court for the 

Northern District of Illinois, Eastern Division. 

Nos. 1:12-cr-00723, 1:13-cr-00703 & 1:15-cr-00487 

Sharon Johnson Coleman, Judge. 

____________________ 

ARGUED SEPTEMBER 25, 2020 — DECIDED NOVEMBER 17, 2020 

____________________ 

Before RIPPLE, BRENNAN, and ST. EVE, Circuit Judges. 

ST. EVE, Circuit Judge. Adel Daoud pressed the button to 

detonate a bomb that would have killed hundreds of innocent 

people in the name of Islam. Fortunately, the bomb was fake, 

and the FBI arrested him on the spot. Two months later, while 

in pretrial custody, Daoud solicited the murder of the FBI 

agent who supplied the fake bomb. Two and a half years later, 

while awaiting trial on the first two charges, Daoud tried to 
2 Nos. 19-2174, 19-2185 & 19-2186

stab another inmate to death using makeshift weapons after 

the inmate drew a picture of the Prophet Muhammad. Daoud 

eventually entered an Alford plea, and the cases were consolidated for sentencing. The district court sentenced Daoud to a 

combined total of 16 years’ imprisonment for the crimes. The 

government appeals that sentence on the ground that it was 

substantively unreasonable. We agree. We vacate the sentence 

and remand for resentencing. 

I. Background 

A. FBI Investigation and Bomb Plot 

Daoud came to the FBI’s attention after a series of online 

posts, communications, and searches that evinced a desire to 

engage in violent jihad (terrorist attacks in the name of Islam). 

This online activity began as early as September 2011, the 

month that Daoud turned 18. At the time, Daoud was living 

with his parents in a suburb of Chicago. In his online posts 

and communications, Daoud described himself as a “terrorist;” wrote that he wanted to die a martyr; shared songs about 

violent jihad; and encouraged killing and dying in the name 

of Allah and committing violent acts of jihad against the 

United States as revenge for its killing of Muslims. Daoud also 

sought out, consumed, and shared violent jihadist materials, 

including Inspire magazine, an English-language publication 

by al-Qaeda that promotes violent jihad and teaches readers 

how to create and use weapons and destructive devices like 

bombs. 

In May 2012, to assess Daoud’s threat level, two undercover FBI agents initiated online contact with him using fictitious identifies. One of the agents posed as a 17-year-old Arab 

youth living in Australia. The other posed as an older Arab 
Nos. 19-2174, 19-2185 & 19-2186 3 

man living in Saudi Arabia. One of the agents contacted 

Daoud by email to praise a song that Daoud had posted on 

Yahoo Answers and described as “Terrorist Music.” The other 

agent initiated contact a few days later. With the agents’ 

(false) interest and encouragement, Daoud began sharing jihadist materials with them, including Inspire. He also conveyed his interest in engaging in violent jihad and referenced 

his recruitment efforts and plans for an attack in the United 

States or overseas. When one of the agents questioned the propriety of taking lives, Daoud explained why it was justified. 

At one point, Daoud said: “I want to be even worse to the 

Americans, the [sic] Osama bin Laden and sheikh Anwar alAwlaki put together. I want to be a great terrorist ... and be 

great encouragement for Muslims to do the same.” Other 

times, though, Daoud himself questioned the propriety of terrorism. He also referenced his “procrastination” and “laziness,” saying, “All I do is talk.” Sometimes he mentioned 

plans to go to college abroad. While communicating with the 

undercover agents, Daoud continued researching and sharing 

jihadist materials. For example, he inquired about the price of 

an AK-47 and sought information about the propriety of 

blowing up a train, bringing down a flight, and assembling 

explosives. 

In conversations with Daoud, one of the agents referenced 

a fictitious cousin named “Mudafar,” who was supposedly an 

operational terrorist living in the United States. Eventually, 

the agent connected Daoud with a third undercover FBI agent 

posing as Mudafar. Between July and September 2012, Daoud 

and the 38-year-old Mudafar communicated electronically 

and met in person six times. At their first meeting, Daoud 

identified himself as a terrorist and expressed his interest in 

committing a terrorist attack in the United States or overseas. 
4 Nos. 19-2174, 19-2185 & 19-2186

He suggested using “flying cars” or driving a truck with 

knives on it through a crowded area. At Mudafar’s urging, 

Daoud compiled a list of potential locations for a terrorist attack. The list included shopping malls, nightclubs, bars, liquor stores, and military bases. Daoud shared the list with 

Mudafar at their second meeting. He also latched onto 

Mudafar’s idea of using a car bomb. Daoud emphasized the 

importance of inflicting mass casualties, making international 

news, and ensuring that people knew “Muslim extremists” 

were responsible for the attack. When Mudafar questioned 

Daoud’s resolution, Daoud assured him, “this is in my heart.” 

Nevertheless, Daoud wavered at some points and sought religious guidance from Mudafar and Mudafar’s fictional 

sheikh (leader) about the propriety of killing people. Daoud 

also clarified his personal limitations, saying he could not 

make a bomb or “do anything” by himself, and describing his 

ideas as “crazy fantasies.” 

Eventually, Daoud found “the perfect place” for a carbomb attack: Cactus Bar & Grill in Chicago. Daoud explained 

that Cactus was a prime target because it was a crowded 

night-time destination. Daoud and Mudafar began planning 

the attack. Daoud surveilled and photographed the location 

and picked a site for the car bomb. Mudafar described the 

bomb that he would supply and the mass carnage it would 

cause. Daoud expressed pleasure with the bomb’s size. On the 

day before the planned attack, Mudafar showed Daoud the 

(fake) 1,000-pound car bomb, which he had installed in a Jeep 

Cherokee. Daoud said he wanted to have “direct action” in 

the attack and asked if he could press the button to detonate 

the bomb. 
Nos. 19-2174, 19-2185 & 19-2186 5 

On the night of September 14, 2012, Mudafar and Daoud 

met to carry out the planned attack. On the drive over, Daoud 

prayed aloud for the many people who would be killed. He 

also prayed for the attack to make international news, and 

that it not be his last operation. Once there, Daoud parked the 

Jeep in front of the Cactus bar. In a nearby alley, Mudafar told 

Daoud that there were 200 people in the area. Daoud responded: “[T]his is like the lottery.” Shortly before pressing 

the button, Daoud asked if women could be killed in the 

United States. Mudafar said yes. Daoud was arrested upon 

pressing the button. 

Daoud was charged with attempting to use a weapon of 

mass destruction, in violation of 18 U.S.C. § 2332a(a)(2)(D) 

(Count 1) and attempting to destroy a building used in interstate commerce with an explosive, in violation of 18 U.S.C. 

§ 844(i) (Count 2). 

B. Solicitation of FBI Agent’s Murder 

Approximately two months later, while Daoud was in pretrial custody, he solicited the murder of the undercover FBI 

agent who had posed as Mudafar. Daoud offered to pay his 

cellmate, a gang member, to enlist one of his gang associates 

to kill the undercover agent. He gave his cellmate the agent’s 

phone number to help track him down. Daoud’s cellmate reported the offer to federal authorities and agreed to record future conversations with Daoud. In exchange for his cooperation, authorities paid the cellmate $15,000, which he used to 

pay his bond and get out of jail. 

In recorded conversations, Daoud called the undercover 

agent a “spy” and suggested different ways of killing him. He 

asked that the killing be quick and untraceable. More than 
6 Nos. 19-2174, 19-2185 & 19-2186

once, Daoud’s cellmate asked Daoud if was sure he wanted to 

go through with the plan. Daoud said yes. Daoud’s cellmate 

purportedly made the arrangements and confirmed the target 

by showing Daoud a photograph of the undercover agent 

(supposedly taken by his associates but actually provided by 

authorities). Finally, the cellmate instructed Daoud to make a 

phone call authorizing the killing, which Daoud did. When 

the job was done (or so Daoud thought), Daoud asked for the 

“gory details.” Daoud’s cellmate asked Daoud if he regretted 

the decision and Daoud said, “Hell no.” 

On August 29, 2013, Daoud was charged with soliciting a 

crime of violence, in violation of 18 U.S.C. § 373(a) (Count 1); 

murder-for-hire, in violation of 18 U.S.C. § 1958(a) (Count 2); 

and obstruction of justice, in violation of 18 U.S.C. 

§ 1512(a)(1)(A) (Count 3). 

The recorded conversations between Daoud and his cellmate reveal that Daoud’s cellmate was verbally abusive toward him. For example, he mocked Daoud’s religious beliefs, 

called him homosexual as an insult, and threatened to hurt 

him. 

C. Assault on Another Inmate 

In December 2014, a little over two years after soliciting 

the FBI agent’s murder, Daoud physically attacked a fellow 

inmate because the inmate drew a picture of the Prophet Muhammad. Daoud jumped on the inmate and punched him. Before his September 2012 arrest, Daoud had suggested in 

online posts that people who drew pictures of the Prophet 

Muhammad should be killed. 

Daoud and the other inmate later reconciled. But in May 

2015, Daoud sent the same inmate to the hospital after 
Nos. 19-2174, 19-2185 & 19-2186 7 

approaching him in his sleep and stabbing him repeatedly in 

the throat and head using sharpened toothbrushes and a 

toothbrush with a razor blade attached to it. The attack ended 

when the inmate’s cellmate intervened. 

The day before the attack, a news story had aired on the 

jail television about violence toward individuals who drew 

pictures of the Prophet Muhammad. According to another inmate, Daoud was near the television when the story aired and 

seemed agitated. An inmate who witnessed the attacked described Daoud as “zoned out” and “not there.” Daoud described experiencing hallucinations before the attack. 

In August 2015, Daoud was charged with assault with intent to commit murder, in violation of 18 U.S.C. § 113(a)(1) 

(Count 1); assault with a dangerous weapon with intent to do 

bodily harm, in violation of 18 U.S.C. § 113(a)(6) (Count 2); 

assault resulting in serious bodily injury, in violation of 18 

U.S.C. § 113(a)(6) (Count 3); possession of a weapon by an inmate, in violation of 18 U.S.C. §§ 1791(a)(2) and (b)(3) (Count 

4); and simple assault, in violation of 18 U.S.C. § 113(a)(4) 

(Count 5). 

As a result of the assault, Daoud spent seven continuous 

months in the jail’s segregated housing unit. In January 2016, 

while in segregated housing, Daoud witnessed his cellmate 

commit suicide. In total, Daoud spent over 400 days in the 

segregated housing unit during his period of pretrial incarceration. 

D. Pretrial Proceedings and Guilty Plea 

The three criminal cases against Daoud were consolidated 

amidst lengthy pretrial proceedings. In August 2013, after the 

government gave notice of its intent to present evidence 
8 Nos. 19-2174, 19-2185 & 19-2186

obtained under the Foreign Intelligence Surveillance Act 

(FISA), Daoud moved for disclosure of the government’s 

FISA-related materials. The district court granted Daoud’s 

motion in part and ordered disclosure. This Court reversed 

that decision, holding that “there was no basis for disclosure.” 

United States v. Daoud, 755 F.3d 479, 485 (7th Cir. 2014). 

In December 2015, Daoud’s counsel moved for a competency hearing based on Daoud’s assault on a fellow inmate 

and his erratic in-court behavior. At one hearing, for example, 

Daoud told the district court: “I would with the following 

condition be willing to plead guilty to like whatever the hell 

you want to charge me for if you all admit that you’re part of 

the Illuminati and that you arrested me because I’m a Muslim.” Daoud also blamed the district court for his cellmate’s 

suicide. 

After hearing competing psychological testimony, the district court found Daoud incompetent to stand trial because he 

“lack[ed] a rational understanding of the proceedings.” The 

court ordered Daoud to undergo psychological treatment. 

While in treatment, Daoud was diagnosed with unspecified 

schizophrenia and other psychotic disorder (a rule-out diagnosis), and antisocial personality disorder. With medication, 

Daoud’s condition improved significantly. On March 12, 

2018, the court found Daoud competent to stand trial. 

The court scheduled Daoud’s trial for November 26, 2018. 

On the eve of trial, however, Daoud moved to plead guilty 

while maintaining his innocence, pursuant to North Carolina 

v. Alford, 400 U.S. 25 (1970). The court granted his motion over 

the government’s objection. Daoud pled guilty to all the 

counts against him, admitting that the government’s evidence 
Nos. 19-2174, 19-2185 & 19-2186 9 

supported a conviction on each count but denying culpability 

and persisting in his innocence. 

E. Sentencing 

The parties agreed that the advisory Guidelines range was 

life imprisonment. The government recommended 40 years’ 

imprisonment, stressing Daoud’s predisposition to commit 

acts of terrorism, the seriousness of his three interrelated 

crimes, and sentences imposed in similar cases. Daoud’s lawyer asked for nine years’ imprisonment, with credit for the 

seven years that Daoud had already served. He stressed 

Daoud’s age, mental health issues, the harsh conditions of his 

pretrial confinement, his susceptibility to influence, and the 

government’s “imperfect entrapment.” Without the FBI’s involvement, he argued, Daoud would have lacked the ability 

and drive to attempt an act of mass terrorism. Daoud’s probation officer recommended a sentence of 15 years. 

The court held an evidentiary hearing that spanned four 

days. The government called two FBI agents, including the 

undercover agent who had posed as Mudafar, to testify about 

the investigation. The government also presented video testimony from the inmate whom Daoud had attacked. The inmate testified to his belief that Daoud would have killed him 

if his cellmate had not intervened. Daoud introduced video 

recordings from his former teacher, counselor, and sheikh 

about their positive interactions with him. Daoud’s father testified about Daoud’s mental health and the impact of Daoud’s 

crimes on their family. 

After the parties presented evidence, Daoud presented his 

allocution. He told the court, “I can’t express how sorry I am 

for my actions.” Upon reflection, Daoud concluded that he 
10 Nos. 19-2174, 19-2185 & 19-2186

had been “naive, gullible, and confused” in his beliefs about 

fighting for Islam. He attributed those views to a misinterpretation of the teachings of Islam. With respect to the bomb plot, 

he stated that he “should have been more assertive” with 

Mudafar. “I learned that I have to make my own decisions 

and not let someone else make them for me.” Still, he apologized for “whatever part I took in the events.” He disavowed 

any intent to engage in terrorism. “I don’t want to kill people 

or join a terrorist group whether it’s something condoned by 

my religion or not.” On the topic of his online postings, he 

stated, “the way I see myself in 2012 is some idiot trying to 

make friends.” He apologized for the inmate attack, adding, 

“I do not think I would have done that if I was on the medication I’m taking.” “Now that I’m aware of my mental disorders, I’m working to make better decisions.” He closed by 

apologizing to the court, his parents, the Muslim community, 

and the United States. 

The court sentenced Daoud to a total of 192 months (16 

years) of prison, with 45 years of supervised release to follow. 

The breakdown of prison terms was: 192 months for both 

counts in the attempted-bombing case, to run concurrently; 

120 months on counts 1 and 2 and 140 months on count 3 in 

the solicitation case, all to run concurrently with each other 

and the other sentences; and 120 months on counts 1 through 

3, 60 months on count 4, and 12 months on count 5 in the assault case, all to run concurrently with each other and the 

other sentences. 

The court explained the factors that it had considered in 

arriving at its sentence. It began with the nature and circumstances of the offense. It described the bomb plot as “a violent 

and heinous act to kill or harm others,” the seriousness of 
Nos. 19-2174, 19-2185 & 19-2186 11 

which “cannot be understated or downplayed.” “[S]uch an attempt clearly deserves the possibility of a prolonged sentence, 

including life in prison.” Similarly, on the solicitation offense, 

the court remarked that “[a]ny attempt to harm the law enforcement personnel for doing to job they swore to do must 

be addressed with serious consequences.” Turning to the inmate assault, the court noted that “the harm caused to the inmate was serious and violent.” In short, “the crimes the defendant has pled guilty to are all serious and deserve serious 

sentences.” 

The court next addressed Daoud’s history and characteristics. The court described Daoud in 2012 as an “awkward” 

and “immature” youth “with few friends” who “giggled constantly.” As such, he was “immediately drawn” to the undercover agents, who validated his political and religious beliefs. 

The court described Daoud’s misguided and sometimes fantastical comments (about flying cars, for example) as “bravado,” and credited Daoud’s argument that it was the FBI, 

and not Daoud, that chose the 1,000-pound bomb, when it 

could have selected a less severe option. After all, Daoud “did 

not know how to build a bomb.” At the same time, Daoud’s 

“teenage goofiness” and sometimes “nonsensical comments” 

did “not equal a finding that in 2012 the defendant was mentally ill.” “Clearly he believed he was detonating a bomb that 

would cause human deaths and injuries and would put him 

in a place of favor with the Prophet Muhammad, Allah himself, or his religion.” 

With respect to the solicitation offense, the court stressed 

that Daoud was sharing a cell with a “multi-convicted gangbanger” who verbally abused him. Still, Daoud admitted “to 

following through on some of the steps directed by [the 
12 Nos. 19-2174, 19-2185 & 19-2186

cellmate] that support his conviction and a sentence for deterrence.” “Cellmate banter should not outweigh the seriousness 

of threats on the lives of law enforcement.” Prior to inmate the 

assault, the court noted that Daoud “had been in restrictive 

confinement for more than one year.” Nonetheless, Daoud’s 

“inability to control himself where someone is not physically 

attacking him deserves punishment,” even if Daoud was 

“zoned out” during the attack.

The court moved next to deterrence and public safety. It 

discussed the need for both general and specific deterrence 

for each of Daoud’s crimes. It was hopeful that Daoud would 

not reoffend, given his maturity, remorse toward his parents, 

and improvement with medication. But “[t]he possibility that 

Daoud could be co-opted or persuaded again is one that cannot be ignored. At least not at this time.” 

The court then turned to additional mitigating factors. 

These included Daoud’s “laudable” college aspirations, his 

diagnosed mental illness, his family and teacher support, and 

his long and “traumatizing” period of pretrial incarceration, 

which began when he was only 18. The court also noted that 

Daoud had generally “been respectful and pleasant to this 

Court at all times. More so than probably any defendant in 

custody I have had.” Finally, the court emphasized that it did 

“not consider the Alford plea that [Daoud] made in November 

a failure to take responsibility. In fact, through the plea on the 

eve of trial and his allocution this Court finds that Mr. Daoud 

has taken responsibility.” 

Before finalizing its sentence, the court addressed the parties’ sentencing recommendations. It stressed that the cases 

cited by the parties in support of their recommendations were 

all distinguishable “on one very important point that the 
Nos. 19-2174, 19-2185 & 19-2186 13 

Court is going to rely on, and that is the lengthy detention that 

Daoud has endured,” ever since he was first detained at the 

age of 18. The court responded to the government’s argument 

(which the government disputes making) that Daoud’s three 

convictions were for “one course of conduct” by saying, “the 

Court will continue to consider it so even though they came 

at different times and must receive different sentences. But the 

Court does not see one case as being aggravating of the other 

case.” 

After imposing its sentence, the court walked through the 

terms of Daoud’s supervised release. Those conditions included mental health treatment, electronic monitoring, and 

“violent extremism counseling.” Daoud’s counsel clarified on 

the record that violent extremism counseling did not currently exist but “it’s the intention of the government that it’s 

going to exist.” 

After the sentencing hearing, the court issued a written 

statement of reasons for its sentence: 

This sentence addresses the safety of Americans and 

the future of Adel Daoud who has spent his entire 

adulthood in the bureau of prisons including more 

than a year in the Special Housing Unit. Daoud committed 3 violent or potentially violent offenses born out 

of immaturity, bad judgment and the problems with 

growing up in an intensely anti-Muslim environment 

where violence against Muslims is referred to directly 

or indirectly by Americans. The federal undercover 

employee sympathized with Daoud’s angst and encouraged his feelings. Most of all, the [agent] was a 

friend who had no friends. The line between teenaged 

awkwardness and zealot violent Jihad can be grey but 
14 Nos. 19-2174, 19-2185 & 19-2186

clearly this young man might have been susceptible to 

a much less violent method of revolution if it had been 

presented instead of a 1000 lb. bomb. During his time 

in federal custody he has also witnessed a cellmate’s 

suicide, been cellmates with a truly hardened and abusive prisoner and been taunted by others about his religion and faith while being separated from his close 

family for 7 years. During this incarceration he has 

mentally deteriorated requiring constant psychotropic 

drugs after violent outbursts or no responsiveness. 

Daoud entered prison barely 18 and won’t leave until 

mid-30s. Supervised Release for 45 years of monitoring 

should address the safety of the public with the possibility of salvaging the life of a young man. 

The government appeals the district court’s sentence as substantively unreasonable. 

II. Discussion 

The government argues that the district court’s 16-year 

sentence was substantively unreasonable given Daoud’s “exceptionally serious” criminal conduct and the corresponding 

need to protect the public. It faults the district court for relying on mitigating factors that could not “bear the weight” that 

it assigned to them, and for failing to sentence Daoud in accordance with similar offenders. 

District courts must impose sentences that are “‘sufficient, 

but not greater than necessary, to comply with’ the basic aims 

of sentencing.” Rita v. United States, 551 U.S. 338, 348 (2007) 

(quoting 18 U.S.C. § 3553(a)). Those “basic aims” are just punishment, deterrence, incapacitation, and rehabilitation. Id. at 

347–48. Before selecting a sentence, a district court must 
Nos. 19-2174, 19-2185 & 19-2186 15 

consider the factors set forth in § 3553(a): the nature and circumstances of the offense; the defendant’s history and characteristics; the need for the sentence to reflect the seriousness 

of the offense, promote respect for the law, provide just punishment, deter crime, protect the public, and provide the defendant with training, medical care, or other correctional 

treatment; the kinds of sentences available; the United States 

Sentencing Commission’s recommended sentencing ranges 

and policy statements; the need to avoid unwarranted sentencing disparities among similar defendants; and the need 

for victim restitution. § 3553(a). 

We review the substantive reasonableness of the district 

court’s sentence for abuse of discretion. Gall v. United States, 

552 U.S. 38, 51 (2007). “When conducting this review, the 

court will, of course, take into account the totality of the circumstances, including the extent of any variance from the 

Guidelines range.” Id. A “major departure” from the advisory 

Guidelines range “should be supported by a more significant 

justification than a minor one.” Id. at 50. “In reviewing sentences for substantive reasonableness, we do not substitute 

our judgment for that of a district judge, who is better situated 

to make individualized sentencing decisions.” United States v. 

Porraz, 943 F.3d 1099, 1104 (7th Cir. 2019). We will not reverse 

unless the district court’s sentence falls outside “the broad 

range of objectively reasonable sentences in the circumstances.” United States v. Warner, 792 F.3d 847, 856 (7th Cir. 

2015) (internal quotation marks and citation omitted). 

For several reasons, the district court’s sentence in this 

case fell outside the range of reasonable sentences. First, the 

court downplayed the extreme seriousness of Daoud’s offenses in ways that conflict with the undisputed facts. Second, 
16 Nos. 19-2174, 19-2185 & 19-2186

the court failed to account for the need to protect the public 

from Daoud’s demonstrably high risk of reoffending. Third, 

the court improperly distinguished the sentences of similar 

offenders by relying on Daoud’s long period of pretrial confinement. Finally, the court premised its well-below-Guidelines sentence on mitigating factors that could not bear the 

heavy weight that it assigned to them, given the facts in this 

case. 

A. Seriousness of the Offenses 

Section 3553(a)(2)(A) instructs district courts to consider 

the need for the sentence imposed to reflect the seriousness of 

the offense. In this case, the district court’s sentence failed to 

account for the extreme seriousness of Daoud’s offenses. 

To be sure, the district court acknowledged that Daoud 

committed three serious crimes that “deserve[d] serious sentences.” It described the bomb plot as “a violent and heinous 

act to kill or harm others” that “clearly deserve[d] the possibility of a prolonged sentence, including life imprisonment.” 

And it recognized that Daoud “believed he was detonating a 

bomb that would cause human deaths and injuries and would 

put him in a place of favor with the Prophet Muhammad, Allah himself, or his religion.” Similarly, the court remarked 

that any attempt to harm law enforcement “must be addressed with serious consequences,” and that light sentences 

for threats on the lives of law enforcement put law enforcement at risk. It also called Daoud’s assault on a fellow inmate 

“serious and violent.” 

Yet the court went on to effectively negate these statements 

and the severity of the violent crimes by characterizing 

Daoud’s crimes as the misguided actions of an 
Nos. 19-2174, 19-2185 & 19-2186 17 

impressionable teenager who let others get the best of him. 

The court portrayed Daoud as an “awkward” and “immature” young man “with few friends” who was trying to impress his false friends, the undercover FBI agents. It credited 

Daoud’s argument that he lacked the capacity to carry out a 

terrorist attack by himself, thus minimizing Daoud’s agency 

in the bomb plot. The court described at length the verbal 

abuse and intimidation that Daoud’s gang-member cellmate 

visited upon him, and then acknowledged in passing that 

Daoud admitted “to following through on some of the steps 

directed by [the cellmate] that support his conviction and a 

sentence for deterrence.” It blamed the inmate assault on 

Daoud’s mental health issues and the conditions of jail, which 

make “physical altercations” inevitable, while allowing that 

“Daoud’s inability to control himself where someone is not 

physically attacking him deserves punishment.” More 

broadly, the court framed Daoud’s risk of reoffending as a 

risk that he would be “co-opted or persuaded again.” 

These sanitized accounts are impossible to square with the 

undisputed offense conduct and the objective seriousness and 

violent nature of the crimes to which Daoud pled guilty. 

Daoud committed three discrete, premeditated criminal acts 

that exhibited an extraordinary disregard for human life. 

First, he excitedly participated in a plot to detonate a bomb 

that would have killed hundreds of innocent people. In the 

year leading up to the attempted bombing, Daoud voraciously consumed violent jihadist materials, shared them 

with others, and repeatedly expressed his desire to commit a 

terrorist attack. He took an active role in the bomb plot, helping to plan it over the course of months and then asking to 

press the button to detonate the bomb that he anticipated 

would kill hundreds of people and receive national attention. 
18 Nos. 19-2174, 19-2185 & 19-2186

He had countless opportunities to back out, yet he continually 

reaffirmed his commitment. These are not the actions of an 

immature and impressionable youth trying to impress his 

friends. Although he occasionally expressed some doubts 

along the way, Daoud willingly and proactively participated 

in a plot to commit mass terrorism from start to finish, including pressing the button of what he thought was a 1,000-pound 

bomb. 

Next, Daoud solicited the murder of the FBI agent who 

acted in the undercover capacity in the bomb plot. The record 

is not clear as to whether Daoud or his cellmate first broached 

the subject of murdering the FBI agent. But either way, Daoud 

played a central role. He gave his cellmate the FBI agent’s 

phone number to help track him down. He gave instructions 

for how the murder should be carried out. He confirmed the 

target by photograph. He made a phone call authorizing the 

murder. And he expressed satisfaction, asked for the gruesome details, and disclaimed regret when he thought it was 

over. Undoubtedly, Daoud’s cellmate had an interest in helping Daoud commit the offense. But the record does not reflect 

that Daoud’s cellmate somehow pressured him into committing the crime. To the contrary, Daoud’s cellmate gave him 

multiple attempts to back out, which Daoud rejected. Daoud’s 

cellmate may have mistreated Daoud and had a long criminal 

history, but that does not detract from Daoud’s full and active 

participation in the attempted murder of an FBI agent. 

Finally, Daoud brutally attacked a fellow inmate with 

makeshift weapons while he was sleeping. He stabbed him 

repeatedly in the throat and head. The inmate testified that he 

thought he would have died absent quick intervention. The 

district court’s view of this crime—embodied in its comment 
Nos. 19-2174, 19-2185 & 19-2186 19 

that “Daoud’s inability to control himself where someone is 

not physically attacking him deserves punishment”—reflects 

a misunderstanding of its severity. Daoud did not simply “fail 

to control himself.” He planned and executed a deliberate attempt to murder a fellow inmate in his sleep. 

In short, while the district court paid lip service to the seriousness of the offenses, it undercut its own statements by 

unreasonably downplaying Daoud’s role in each offense. District courts have broad discretion as to how to weigh the 

§ 3553(a) factors, but a district court’s sentence must reflect a 

reasonable view of the facts and a reasonable weighing of the 

§ 3553(a) factors. See Warner, 792 F.3d at 856; United States v. 

Goldberg, 491 F.3d 668, 673 (7th Cir. 2007). Here, the district 

court sterilized Daoud’s offense conduct in ways that cannot 

be reconciled with the objective facts of these violent offenses. 

That unreasonable view of the facts prevented the district 

court from properly weighing the seriousness of the offenses 

when selecting its sentence. See United States v. Mumuni Saleh, 

946 F.3d 97, 106 (2d Cir. 2019) (holding that a district court’s 

sentence was substantively unreasonable because the court 

“drastically discounted the seriousness of Mumuni’s offense 

conduct based on a sterilized and revisionist interpretation of 

the record”). 

B. Need to Protect the Public 

Section 3553(a)(2)(C) instructs district courts to consider 

the need for the sentence imposed to protect the public from 

the defendant’s future crimes. Although the district court referenced this factor in the abstract, it failed to account for the 

need to protect the public from Daoud’s demonstrably high 

risk of recidivism. 
20 Nos. 19-2174, 19-2185 & 19-2186

The court acknowledged that it needed to fashion a sentence that would protect the public, but its discussion of public safety was otherwise perfunctory. It considered the need 

to protect the public alongside the related factor of deterring 

future crimes. See § 3553(a)(2)(B). It described Daoud as “contrite at causing his family so much pain,” and said it did not 

think he would risk causing them pain again. The court expressed hope that Daoud’s improvement with medication, 

along with his continued maturity, would prevent him from 

reoffending. Still, it acknowledged that the “possibility that 

Daoud could be co-opted or persuaded again is one that cannot be ignored. At least not at this time.” 

Noticeably absent from the court’s discussion of protecting the public was any acknowledgment of Daoud’s demonstrated commitment to reoffending in extremely serious 

ways. Daoud recidivated twice over a short period of time 

while he was in jail pending trial in the attempted-bombing 

case. He solicited the murder of an FBI agent, then he tried to 

stab another inmate to death. These additional life-threatening crimes—committed while in pretrial detention, under 

government supervision—show a remarkable propensity for 

criminal activity. Yet the court somehow thought that Daoud 

posed a minimal risk of recidivism and did not “see one case 

as being aggravating of the other case.” The court apparently 

blamed Daoud’s third offense partially on the conditions of 

confinement. But if Daoud was able to continue his streak of 

gravely serious criminal activity while detained, one can only 

imagine what he might have done if released. 

To be sure, mental health issues may present a mitigating 

factor and “a sentencing judge may consider whether mental 

health treatment will succeed in reducing the defendant’s 
Nos. 19-2174, 19-2185 & 19-2186 21 

dangerousness or propensity to commit further crimes.” 

United States v. Kluball, 843 F.3d 716, 718 (7th Cir. 2016). But, 

as Daoud concedes, there is no evidence that he was mentally 

ill when he committed the first two crimes. His improved 

mental health is thus no guarantee that he will not reoffend. 

The need to protect the public was an especially relevant 

factor in this case. The court gave short shrift to it and essentially ignored facts showing that Daoud “plainly pose[d] a 

heightened risk of recidivism.” United States v. Jordan, 435 F.3d 

693, 697 (7th Cir. 2006). The court’s analysis of this § 3553(a) 

factor was unreasonable. 

C. Need to Avoid Sentencing Disparities 

Section 3553(a)(6) instructs district courts to consider “the 

need to avoid unwarranted sentence disparities among defendants with similar records who have been found guilty of 

similar conduct.” Here, both parties brought the sentences of 

similar offenders to the district court’s attention. But the court 

found them all distinguishable, largely because of Daoud’s 

lengthy pretrial detention. That was legal error. No matter 

what sentence he receives, Daoud will receive credit for his 

time in pretrial detention for his charged offenses. 18 U.S.C. 

§ 3585(b); United States v. Wilson, 503 U.S. 329, 333 (1992). As 

such, there was no reason for the court here to consider the 

length* of pretrial confinement as a reason to impose a substantially lower sentence. See United States v. Jayyousi, 657 F.3d 

1085, 1119 n.6 (11th Cir. 2011). Doing so could only result in a 

* We discuss below the separate issue of whether the court properly 

considered the conditions of Daoud’s pretrial confinement in mitigation. 
22 Nos. 19-2174, 19-2185 & 19-2186

windfall for Daoud, who would receive double credit for his 

time in pretrial detention. 

Daoud’s period of pretrial detention was not a valid basis 

for distinguishing the sentences of similar offenders. The 

court’s legal error prevented it from appropriately weighing 

this § 3553(a) factor. 

D. Mitigating Factors 

Daoud’s 16-year sentence was a significant downward departure from the advisory Guidelines range. Whereas the 

Guidelines recommended life imprisonment, the court’s sentence would have released Daoud from prison around his 

35th birthday (without regard to the possibility of good-time 

credit). A major departure from the Guidelines range requires 

a major justification. See Gall, 552 U.S. at 51. The district court 

spent most of its time discussing mitigating factors, but the 

factors it relied on do not justify its significant downward departure. 

In the district court’s telling, Daoud’s age, mental health, 

and general awkwardness and impressionability converged 

to render him uniquely susceptible to criminal influence. A 

sentencing court is well within its rights to consider a defendant’s mental limitations in mitigation. See, e.g., United States v. 

Cunningham, 429 F.3d 673, 678 (7th Cir. 2005). But that factor 

only goes so far in this case. Daoud committed the attempted 

bombing around his 19th birthday. He was 19 when he solicited the FBI agent’s murder and 21 when he tried to stab a 

fellow inmate to death. In other words, he was college aged at 

all relevant times. He may have been immature, but, as the 

court recognized, he was old enough to know what he was 

doing. As for mental health, the court properly considered 
Nos. 19-2174, 19-2185 & 19-2186 23 

Daoud’s diagnosed mental illness as a mitigating factor in the 

inmate assault. See id. But there is no evidence that Daoud suffered from a mental illness at the time of the first two offenses, 

so that factor had limited significance as well. The court’s 

more general emphasis on Daoud’s awkwardness, goofiness, 

and impressionability is puzzling. We do not see how social 

ineptitude could excuse repeated violent criminal behavior 

that reflected an extraordinary disregard for human life. And 

even if it could, the record does not support the court’s apparent conclusion that Daoud’s crimes were the product of his 

social shortcomings and impressionability. Daoud had help 

from others in committing the first two crimes, but he played 

a very active role in both offenses and his motivation to commit serious criminal conduct, including deadly terrorist attacks, preceded his interactions with the FBI and his cellmate. 

In a similar vein, the court accepted Daoud’s argument 

that the FBI shared responsibility for the seriousness of the 

attempted bombing because it chose to supply a 1,000-pound 

bomb when it could have selected a less severe option. But the 

FBI agent who supplied the bomb testified that he chose a 

large bomb to ensure that Daoud understood the gravity of 

the crime that they were plotting. The FBI agent repeatedly 

reminded Daoud of the mass casualties that the bomb would 

cause. Far from deterring him, the undisputed record shows 

that the possibility of mass casualties excited and motivated 

Daoud. He described the prospect of killing hundreds of people as “like the lottery.” At best, the size of the bomb is a “twoedged” factor. United States v. Roberson, 474 F.3d 432, 435 (7th 

Cir. 2007), abrogated on other grounds by Dean v. United States, 

137 S. Ct. 1170 (2017). On one hand, the government could 

have supplied a smaller bomb. On the other hand, the large 
24 Nos. 19-2174, 19-2185 & 19-2186

bomb illustrates that Daoud had an apparently large appetite 

for mass carnage. 

Another factor that the court found mitigating was 

Daoud’s harsh experience in pretrial confinement—which included more than a year in the segregated housing unit. “Pretrial conditions of confinement are not included in the 

§ 3553(a) factors,” and the Seventh Circuit has “not decided 

whether extraordinarily harsh conditions of confinement 

could ever justify a reduced sentence.” United States v. Campos, 541 F.3d 735, 751 (7th Cir. 2008). Other circuits have held 

that extreme conditions of pretrial confinement may allow for 

a downward departure. See, e.g., United States v. Pressley, 345 

F.3d 1205, 1219 (11th Cir. 2003) (holding that five years spent 

in 23-hour-a-day lockdown with no outside access permitted 

a two-and-a-half-year downward departure). 

We need not decide in this case whether harsh conditions 

of pretrial confinement could ever justify a downward departure. We decide only that Daoud should not receive credit for 

his time in segregated housing. The record does not support 

the conclusion that Daoud’s time in segregated housing involved extraordinarily harsh conditions. Moreover, Daoud 

earned his time in segregated housing by committing violent 

offenses while housed in the general jail population. Daoud 

spent seven months in segregated housing because he tried to 

murder a fellow inmate with makeshift weapons. All told, it 

appears that he spent more than a year in segregated housing. 

Although the record is not entirely clear, it appears that all of 

Daoud’s time in segregated housing resulted from his own 

dangerous and criminal behavior that he engaged in while incarcerated. Under these circumstances, Daoud’s time in segregated housing is not a mitigating factor. At the same time, 
Nos. 19-2174, 19-2185 & 19-2186 25 

we do not fault the district court for considering the effect that 

Daoud’s cellmate’s suicide may have had on Daoud’s mental 

health. 

Finally, the other factors that the court found mitigating 

do not justify its substantial downward departure. The court 

found, for example, that Daoud had accepted responsibility 

for his crimes. Even if that were true, it would have limited 

relevance in mitigation. Acceptance of responsibility normally factors into the advisory Guidelines calculation if a defendant pleads guilty. See USSG § 3E1.1. Here, Daoud did not 

receive this benefit because he pled guilty while maintaining 

his innocence. The court was entitled to credit Daoud’s statements of remorse in allocution. But a defendant’s apology, 

even if sincere, does not justify a significant downward departure in a case involving such extremely serious criminal conduct that reflects a disdain toward other human lives. Even 

less relevant was Daoud’s polite in-court behavior. A defendant’s good behavior in court has minimal value in mitigation. 

Cf. Mumuni, 946 F.3d at 112 (“[N]o substantially mitigating 

weight can be borne here by the fact that Mumuni did what 

was plainly required of him—that is, behaving himself in 

prison.”). And the other factors that the court found mitigating—Daoud’s college aspirations and family support—were 

not weighty enough to justify the extent of the downward departure. 

In sum, the district court relied on factors that could not 

“bear the mitigating weight assigned to them.” Mumuni, 946 

F.3d at 112. As a result, the court’s mitigation analysis did not 

justify its substantial downward departure from the advisory 

Guidelines range. 
26 Nos. 19-2174, 19-2185 & 19-2186

For his part, Daoud defends the district court’s sentence 

because it was higher than probation’s recommended sentence of 15 years, and because it included 45 years of supervised release. But probation’s sentencing recommendations 

only inform a judge’s sentencing decision—they do not bind 

a judge or otherwise limit the judge’s discretion. United States 

v. Schuler, 34 F.3d 457, 461 (7th Cir. 1994). And while supervised release is part of a sentence, and an appellate court 

should consider it when reviewing the sentence, see Gall, 552 

U.S. at 48, a long term of supervised release cannot save a sentence that rests on an unreasonable application of the 

§ 3553(a) factors. 

III. Conclusion 

We do not call into question a district court’s broad discretion in fashioning sentences. District courts are best situated 

to develop sentences that fit the facts of a crime and the characteristics of a defendant. We substantively review sentences 

only to ensure that they fall within the wide range of options 

that are reasonable under the circumstances. We find that this 

is one of those rare cases where the district court stepped outside of what was permissible under the circumstances. Accordingly, we VACATE the district court’s sentence and 

REMAND for resentencing. Circuit Rule 36 will apply on remand.