### In the 

# United States Court of Appeals For the Seventh Circuit

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

U NITED S TATES OF A MERICA, Plainti ff

-Appellant,

v.

A DEL D AOUD , 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

.

____________________

A RGUED S EPTEMBER 25, 2020

— D ECIDED N OVEMBER 17, 2020

____________________

Before R IPPLE , B RENNAN, and S T

. E VE , Circuit Judges

. S T

. E VE , Circuit Judge . Adel Daoud pressed the bu tt on 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 so licited the murder of the FBI agent who supplied the fake bomb. Two and a half years later, while awaiting trial on the fi rst two charges, Daoud tried to2 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 Alfordplea, and the cases were consolidated for sentencing. The distri ct 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 a tt ention after a series of online posts, communications, and search es that evinced a desire to engage in violent jihad (terrorist a tt acks 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 postsand 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 commi tt ing 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 Inspiremagazine, an English-language publication by al-Qaeda that promotes vi olent 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 fi ctitious identi fi es. One of the agents posed as a 17-year-old Arab youth living in Australia. The other posed as an older ArabNos. 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 e ff orts and plans for an a tt ack in the UnitedStates or overseas. When one of the agents questioned the propriety of taking lives, Daoud explained why it was justi fi ed. At one point, Daoud said: “I want to be even worse to theAmericans, 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 qu estioned the propriety of terrorism. He also referenced hi s “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 cont inued 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 fl ight, and assembling explosives. In conversations with Daoud, one of the agents referenced

a fi ctitious 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 fi rst meeting, Daoud identi fi ed himself as a terrorist and expressed his interest in commi tt ing a terrorist a tt ack in the United States or overseas.4 Nos. 19-2174, 19-2185 & 19-2186

He suggested using “ fl ying 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 shoppi ng 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 in fl icting mass casualties, making international news, and ensuring that people knew “Muslim extremists” were responsible for the a tt ack. 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 fi ctional sheikh (leader) about the prop riety of killing people. Daoud also clari fi ed 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 a tt ack: Cactus Bar & Grill in Chicago. Daoud explained that Cactus was a prime target because it was a crowded night-time destination. Daou d and Mudafar began planning the a tt ack. Daoud surveilled and photographed the location and picked a site for the car bomb. Mudafar described the bomb that he would supply an d the mass carnage it would cause. Daoud expressed pleasure with the bomb’s size. On the day before the planned a tt ack, 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 a tt ack and asked if he could press the bu tt on 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 a tt ack. On the drive over, Daoud prayed aloud for the many people who would be killed. He also prayed for the a tt ack to make international news, and that it not be his last operatio n. Once there, Daoud parked the Jeep in front of the Cactus bar. In a nearby alley, Mudafar toldDaoud that there were 200 people in the area. Daoud responded: “[T]his is like the lo tt ery.” Shortly before pressing the bu tt on, Daoud asked if women could be killed in the United States. Mudafar said yes. Daoud was arrested upon pressing the bu tt on. Daoud was charged with a tt empting to use a weapon of mass destruction, in violatio n of 18 U.S.C. § 2332a(a)(2)(D) (Count 1) and a tt empting 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 MurderApproximately two months later, while Daoud was in pretrial custody, he solicited the murder of the undercover FBI agent who had posed as Mudafar. Daoud o ffered 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’sphone number to help track him down. Daoud’s cellmate reported the o ff er 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 di ff erent ways of killing him. He asked that the killing be quic k and untraceable. More than6 Nos. 19-2174, 19-2185 & 19-2186

once, Daoud’s cellmate asked Daou d if was sure he wanted to go through with the plan. Daou d said yes. Daoud’s cellmate purportedly made the arrangements and con fi rmed the target by showing Daoud a photograph of the undercover agent (supposedly taken by his associat es but actually provided by authorities). Finally, the cellmat e instructed Daoud to make a phone call authorizing the kil ling, 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 regre tt ed 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 in sult, and threatened to hurt him.

C. Assault on Another Inmate In December 2014, a li tt le over two years after soliciting the FBI agent’s murder, Daoud physically a tt acked a fellowinmate 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 afterNos. 19-2174, 19-2185 & 19-2186 7

approaching him in his sleep and stabbing him repeatedly in the throat and head using sh arpened toothbrushes and a toothbrush with a razor blade a tt ached to it. The a tt ack ended when the inmate’s cellmate intervened. The day before the a tt ack, a news story had aired on the jail television about violence toward individuals who drewpictures of the Prophet Muhammad. According to another inmate, Daoud was near the televisi on when the story aired and seemed agitated. An inma te who witnessed the a tt acked described Daoud as “zoned out” and “not there.” Daoud described experiencing hallucinations before the a tt ack.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); poss ession 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 viol ation 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 evidence8 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 di strict court granted Daoud’s motion in part and ordered di sclosure. This Court reversed that decision, holding that “the re 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 behavio r. 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 unspeci fi edschizophrenia and other psychotic disorder (a rule-out diagnosis), and antisocial persona lity disorder. With medication, Daoud’s condition improved signi fi cantly. On March 12, 2018, the court found Daoud comp etent 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 i nnocence, 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, admi tt ing that the government’s evidenceNos. 19-2174, 19-2185 & 19-2186 9

supported a conviction on eachcount 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 interrelatedcrimes, 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 issu es, the harsh conditions of his pretrial con fi nement, his susceptibility to in fl uence, and the government’s “imperfect ent rapment.” Without the FBI’s involvement, he argued, Daoud would have lacked the ability and drive to a tt empt an act of mass terrorism. Daoud’s probation o ffi cer recommended a sentence of 15 years. The court held an evidentiaryhearing that spanned four days. The government called two FBI agents, including the undercover agent who had posed as Mudafar, to testify aboutthe investigation. The government also presented video testimony from the inmate whom Daoud had a tt acked. The inmate testi fi ed 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 sheikhabout their positive interactions with him. Daoud’s father testi fi ed 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 re fl ection, Daoud concluded that he10 Nos. 19-2174, 19-2185 & 19-2186

had been “naive, gullible, and co nfused” in his beliefs about fi ghting for Islam. He a tt ributed 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 decisionsand 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 a tt ack, adding, “I do not think I would have do ne that if I was on the medication I’m taking.” “Now that I’m aware of my mental disorders, I’m working to make be tt er 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 a tt empted-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 mo nths 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 bega n with the nature and circumstances of the o ff ense. It described the bo mb plot as “a violent and heinous act to kill or harm others,” the seriousness ofNos. 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 o ff ense, the court remarked that “[a]ny a tt empt to harm the law enforcement personnel for doing to job they swore to do mustbe 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 fl ying 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 goo fi ness” and sometimes “nonsensical comments” did “not equal a fi nding that in 2012 th e defendant was mentally ill.” “Clearly he believed he was detonating a bomb that would cause human deaths and injuries and would put himin a place of favor with the Prophet Muhammad, Allah himself, or his religion.” With respect to the solicitation o ff ense, the court stressedthat Daoud was sharing a cell with a “multi-convicted gangbanger” who verbally abused him. Still, Daoud admi tt ed “to following through on some of the steps directed by [the12 Nos. 19-2174, 19-2185 & 19-2186

cellmate] that support his convic tion and a sentence for deterrence.” “Cellmate banter should not outweigh the seriousness of threats on the lives of law en forcement.” Prior to inmate the assault, the court noted that Daoud “had been in restrictive

con fi nement for more than one year.” Nonetheless, Daoud’s “inability to control himself wh ere someone is not physically

a tt acking him deserves punishment,” even if Daoud was “zoned out” during the a tt ack.

The court moved next to dete rrence and public safety. It discussed the need for both general and speci fi c deterrence for each of Daoud’s crimes. It was hopeful that Daoud would

not reo ff end, given his maturity, remorse toward his parents, and improvement with medication. But “[t]he possibility thatDaoud 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 fa mily 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 th an probably any defendant in custody I have had.” Finally, the court emphasized that it did “not consider the Alfordplea 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 fi nds that Mr. Daoud has taken responsibility.”

Before fi nalizing 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 theNos. 19-2174, 19-2185 & 19-2186 13

Court is going to rely on, and th at is the lengthy detention that Daoud has endured,” ever since he was fi rst 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 di ff erent times and must receive di fferent sentences. But the Court does not see one case as being aggravating of the other case.” After imposing its sentence, the court walked through theterms of Daoud’s supervised release. Those conditions included mental health treatmen t, electronic monitoring, and “violent extremism counseling.” Daoud’s counsel clari fi ed on the record that violent extr emism counseling did not currently exist but “it’s the intentio n of the government that it’s going to exist.” After the sentencing hearing, the court issued a wri tt en 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 morethan a year in the Special Housing Unit. Daoud commi tt ed 3 violent or potentially violent o ffenses 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 undercoveremployee 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 but14 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 witha 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 monitoringshould 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-yearsentence was substantively unreasonable given Daoud’s “exceptionally serious” criminal conduct and the correspondingneed to protect the public. It faults the district court for relying on mitigating factors that could not “bear the weight” thatit assigned to them, and for failing to sentence Daoud in accordance with similar o ffenders. District courts must impose sentences that are “‘su ffi cient, 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 mustNos. 19-2174, 19-2185 & 19-2186 15

consider the factors set forth in § 3553(a): the nature and circumstances of the o ffense; the defendant’s history and characteristics; the need for the sentence to re fl ect the seriousness of the o ff ense, 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 n eed to avoid unwarranted sentencing disparities among sim ilar 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 signi fi cant justi fi cation than a minor one.” Id. at 50. “In reviewing sentences for substantive reasonab leness, we do not substitute our judgment for that of a district judge, who is be tt er 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 broadrange of objectively reasonable sentences in the circumstances.” United States v. Warner, 792 F.3d 847, 856 (7th Cir. 2015) (internal quotation marks and citation omi tt ed). For several reasons, the distri ct court’s sentence in this case fell outside the range of re asonable sentences. First, thecourt downplayed the extreme seriousness of Daoud’s offenses in ways that con fl ict 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 reo ffending. Third, the court improperly distinguis hed the sentences of similar

o ff enders by relying on Daoud’s long period of pretrial confi nement. 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 O ff enses Section 3553(a)(2)(A) instructs di strict courts to consider the need for the sentence imposed to re fl ect the seriousness of the o ff ense. In this case, the district court’s sentence failed to account for the extreme seriousness of Daoud’s o ff enses. To be sure, the district co urt acknowledged that Daoud commi tt ed three serious crimes that “deserve[d] serious sentences.” It described the bomb plot as “a violent and heinousact 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 wouldput him in a place of favor with the Prophet Muhammad, Allah himself, or his religion.” Similarly, the court remarked that any a tt empt to harm law enforcement “must be addressed with serious consequences,” and that light sentencesfor 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 e ff ectively negate these statements and the severity of the violent crimes by characterizing Daoud’s crimes as the misguided actions of anNos. 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 a tt ack 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 admi tt ed “to following through on some of the steps directed by [the cellmate] thatsupport 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 a tt acking him deserves punishment.” More broadly, the court framed Daoud’s risk of reo ffending as a risk that he would be “co-opted or persuaded again.” These sanitized accounts are impossible to square with the undisputed o ff ense conduct and the objective seriousness and violent nature of the crimes to which Daoud pled guilty. Daoud commi tt ed 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 a tt empted bombing, Daoud voraciously consumed violent jihadist materials, shared them with others, and repeatedly expressed his desire to commit a terrorist a tt ack. He took an active ro le in the bomb plot, helping to plan it over the course of months and then asking to press the bu tt on to detonate the bomb that he anticipated would kill hundreds of people and receive national a tt ention.18 Nos. 19-2174, 19-2185 & 19-2186

He had countless opportunities to back out, yet he continually

rea ffi rmed 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 fi nish, including pressing the bu tt on of what he thought was a 1,000-pound bomb. Next, Daoud solicited the mu rder 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 fi rst 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 con fi rmed the target by photograph. He made a phone call authorizing the murder. And he expressed sati sfaction, asked for the gruesome details, and disclaimed regr et when he thought it wasover. Undoubtedly, Daoud’s cellmate had an interest in helping Daoud commit the o ff ense. But the record does not re fl ect that Daoud’s cellmate someho w pressured him into committing the crime. To the cont rary, Daoud’s cellmate gave him multiple a tt empts 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 a tt empted murder of an FBI agent. Finally, Daoud brutally a tt acked a fellow inmate with makeshift weapons while he was sleeping. He stabbed him repeatedly in the throat and head. The inmate testi fi ed that he thought he would have died absent quick intervention. The district court’s view of this crime—embodied in its commentNos. 19-2174, 19-2185 & 19-2186 19

that “Daoud’s inability to control himself where someone is not physically a tt acking him deserves punishment”—re fl ects a misunderstanding of its severity. Daoud did not simply “fail to control himself.” He planne d 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 o ffenses, it undercut its own statements by unreasonably downplaying Daoud’s role in each o ff ense. District courts have broad discretion as to how to weigh the § 3553(a) factors, but a distri ct court’s sentence must re fl ect 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 o ffense conduct in ways that cannot be reconciled with the objective facts of these violent o ffenses. That unreasonable view of the facts prevented the district court from properly weighingthe seriousness of the o ff enses when selecting its sentence. See United States v. Mumuni Saleh , 946 F.3d 97, 106 (2d Cir. 2019) (holdi ng that a district court’s sentence was substantively unreasonable because the court “drastically discounted the se riousness of Mumuni’s o ffense conduct based on a sterilized and revisionist interpretation of the record”).

B. Need to Protect the Public Section 3553(a)(2)(C) instructs di strict courts to consider the need for the sentence imposed to protect the public fromthe defendant’s future crimes. Although the district court referenced this factor in the abstrac t, it failed to account for the need to protect the public fr om 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 pu blic, but its discussion of public safety was otherwise perfunct ory. 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 notthink he would risk causing them pain again. The court expressed hope that Daoud’s im provement with medication, along with his continued maturity, would prevent him from

reo ff ending. Still, it acknowledged that the “possibility thatDaoud 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 acknow ledgment of Daoud’s demonstrated commitment to reo ffending in extremely serious ways. Daoud recidivated twice over a short period of time while he was in jail pending trial in the a tt empted-bombing case. He solicited the murder of an FBI agent, then he tried tostab another inmate to death. These additional life-threatening crimes—commi tt ed 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 o ffense partially on the conditions of

con fi nement. 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 i ssues may present a mitigating factor and “a sentencing judge may consider whether mental health treatment will succeed in reducing the defendant’sNos. 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 commi tt ed the fi rst two crimes. His improved mental health is thus no guarantee that he will not reo ff end. The need to protect the public was an especially relevant factor in this case. The court ga ve 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 distri ct courts to consider “theneed 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 o ff enders to the district court’s a tt ention. But the court found them all distinguishable, largely because of Daoud’s lengthy pretrial detention. That was legal error. No ma tt er what sentence he receives, Daoud will receive credit for his time in pretrial detention for his charged o ffenses. 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 con fi nement 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 is sue of whether the court properly considered the conditions of Daoud’s pretrial con fi nement 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 de tention was not a valid basis for distinguishing the sentences of similar o ffenders. The court’s legal error prevented itfrom appropriately weighing this § 3553(a) factor. D. Mitigating Factors Daoud’s 16-year sentence was a signi fi cant downward departure from the advisory Guidelines range. Whereas theGuidelines 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 justi fi cation. See Gall , 552 U.S. at 51. Th e district court spent most of its time discussingmitigating factors, but the factors it relied on do not justify its signi fi cant 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 in fl uence. A sentencing court is well within it s 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 commi tt ed the a tt empted bombing around his 19th birthd ay. 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 consideredNos. 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 evid ence that Daoud suffered from a mental illness at the time of the fi rst two o ffenses, so that factor had limited signi fi cance as well. The court’s more general emphasis on Daoud’s awkwardness, goo fi ness, and impressionability is puzzling. We do not see how social ineptitude could excuse repeat ed violent criminal behavior that re fl ected an extraordinary disregard for human life. Andeven 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 impr essionability. Daoud had help from others in commi tt ing the fi rst two crimes, but he played a very active role in both o ffenses 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 responsibilit y for the seriousness of the

a tt empted 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 testi fi ed that he chose a large bomb to ensure that Da oud understood the gravity of the crime that they were plo tt ing. The FBI agent repeatedly reminded Daoud of the mass casu alties 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 prospe ct of killing hundreds of people as “like the lo tt ery.” 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 ha nd, the government could have supplied a smaller bomb. On the other hand, the large24 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 con fi nement—which included more than a year in the segregated housing unit. “Pretrial conditions of con fi nement are not included in the § 3553(a) factors,” and the Seventh Circuit has “not decided whether extraordinarily harsh conditions of con fi nement 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 con fi nement may allow for a downward departure. See, e.g., UnitedStates v. Pressley, 345 F.3d 1205, 1219 (11th Cir. 2003) (holding that fi ve years spent in 23-hour-a-day lockdown with no outside access permi tt ed a two-and-a-half-year downward departure).

We need not decide in this case whether harsh conditions of pretrial con fi nement could ever justify a downward departure. We decide only that Daou d should not receive credit for his time in segregated housing. The record does not supportthe conclusion that Daoud’s time in segregated housing involved extraordinarily harsh conditions. Moreover, Daoud earned his time in segr egated housing by commi tt ing violent

o ff enses 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 thana 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 e ffect 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 Daou d had accepted responsibility for his crimes. Even if that were true, it would have limited relevance in mitigation. Acce ptance of responsibility normally factors into the advisory Guidelines calculation if a defendant pleads guilty. SeeUSSG § 3E1.1. Here, Daoud did not receive this bene fi t because he pled guilty while maintaininghis 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 signi fi cant downward departure in a case involving such extremely serious criminal conduct that re fl ects a disdain toward other human lives. Evenless 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—werenot 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 cour t’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 th e district court’s sentencebecause 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 sentenci ng 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 , 552U.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. ConclusionWe do not call into question a district court’s broad discretion in fashioning sentences. Di strict courts are best situated to develop sentences that fi t the facts of a crime and the characteristics of a defendant. We substantively review sentences only to ensure that they fall wi thin the wide range of options that are reasonable under the circumstances. We fi nd that thisis one of those rare cases where the district court stepped outside of what was permissible under the circumstances. Accordingly, we VACATE the di strict court’s sentence and REMAND for resentencing. Circ uit Rule 36 will apply on remand.