United States of America v. Adel Daoud

Chicago, IL - Criminal defense lawyer represented defendant with

soliciting a crime of violence, (Count 1); murder-for-hire, (Count 2); and obstruction of justice (Count 3) charges.

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

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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

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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 the inmate

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.

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.

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