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Prosecutors to ask for 37-year prison sentence for Roanoke street gang ex-kingpin

Prosecutors are seeking a 37-year prison sentence for the leader of a Roanoke street gang, saying he is responsible for the murders of two young men and a broader, “malign impact on the community’s youth.”

Sean “Denk” Guerrant, 31, is scheduled to be sentenced Wednesday in Roanoke’s federal court.

In a sentencing memorandum filed Wednesday, Assistant U.S. Attorney Matthew Miller wrote that the self-admitted founder of the Rollin’ 30s Crips “preyed upon the youth of the local community; as leader of the gang, Mr. Guerrant actively recruited high school students to join his criminal enterprise.”

“Truly, given all the facts and circumstances of this case, the question is not whether a sentence to 444 months [37 years] of confinement is too severe, but rather whether it is significantly severe to account for the lives that were taken by the gang which Mr. Guerrant established, organized and led,” Miller wrote.

In their own memo, defense attorneys Chris Kowalczuk and Patrick Kenney did not disagree with the government’s recommendation, which would keep their client locked up well past his 60th birthday.

The sentence was part of a plea agreement reached in late November, on the eve of a jury trial that had been scheduled to last three weeks. If U.S. District Judge Michael Urbanski accepts the agreement Wednesday, Guerrant’s punishment will essentially be a formality.

An investigation of the Rollin’ 30s was launched about five years ago, when authorities began to hear reports of what they would later call an organized criminal organization linked to a national street gang formed in Los Angeles.

Run from a Richmond-based ring, the Rollin’ 30s were responsible for gang activities in Roanoke that included initiation rites, drug dealing, beatings, shootings and the murders of two men in 2017 and 2018.

More generally, gangs have been blamed in part for a recent increase in gun violence.

An citywide analysis of shootings in 2020 by the Roanoke Police Department found that 78% of the victims or suspects through early November of that year had either confirmed of suspected links to a gang.

Perhaps the most notorious work of the Rollin’ 30s was the death of 17-year-old Nickalas Lee, who was shot to death in June 2017 — just two weeks after graduating from Patrick Henry High School — as part of a falling out with the gang.

In earlier proceedings, co-defendants Demonte “Murda” Mack and Trayvone “30” Kasey have admitted they killed Lee at the command of Guerrant, who was angry that his close friend was associating with a rival gang.

Originally, Guerrant had ordered a gang member identified in court records only as D.F. to kill Lee because he was reaching out to the Bloods. Lee was adopted, and may have sought out a Bloods member under a mistaken belief that they were half-brothers, prosecutors say.

D.F. refused to kill Lee. At that point, Guerrant ordered Lee to kill D.F. for his disloyalty.

Lee also disobeyed the gang leader’s command, warning D.F. to flee after they were both driven to a northwest Roanoke apartment complex the night of June 14, 2017, under the guise of meeting some girls at a party.

With their anger then redirected at Lee, Mack and Kasey chased him behind an apartment building and took a gun he was carrying. Mack then shot Lee multiple times in the back after he had fallen to the ground.

Although Guerrant was not present and has since said that he did not want Lee to be killed, he did not dispute setting in motion the events that led to the murder.

As described in the government’s sentencing memorandum, Guerrant essentially placed Lee “in the impossible position of kill or be killed.”

“It is no exaggeration to state that Nick Lee gave his life to spare D.F.’s, and it is entirely fair to call Nick Lee a brave young hero,” Miller wrote in the document.

Two weeks after Lee was killed, Guerrant was arrested on state charges of possessing a gun after police received a report of shots fired in the parking lot of a sports bar on Bridge Street Southwest.

A Roanoke Circuit Court judge later sentenced him to 28 years in prison for that offense and for violating the conditions of his earlier release on a second-degree murder conviction. In 2007, when Guerrant was 16 years old, he was convicted along with four other teens of stomping a man to death over a $5 debt.

As part of the federal plea agreement, the 37-year sentence for racketeering conspiracy and conspiring to commit a murder in aid of racketeering will run concurrently with the 28 years that Guerrant is currently serving on the state charges. In other words, he will have nine more years of federal time after the completion of his state sentence.

While locked up in the city jail, Guerrant continued to run the Rollin’ 30s, prosecutors say.

In 2018, Mack and Kasey encountered Markel Girty near the Lansdowne Park public housing complex, where the Rollin’ 30s were known to sell cocaine and other drugs out of a “trap house.” Girty was shot and killed after a dispute broke out over the marijuana he was carrying.

Guerrant was culpable, federal prosecutors say, even though he was behind bars at the time.

“The murder of Markel Girty by gang member Trayvone Kasey, robbing him of his marijuana, is exactly the sort of criminal act that anyone in Mr. Guerrant’s position would have known was inevitable once he set the Rollin’ 30s on its path of organized street crime,” Miller wrote.

Miller’s eight-page memorandum also details how the gang infiltrated life in the city’s school system.

One student told authorities that she watched from William Fleming High School, via a live stream on Facebook, a gang initiation in which a Patrick Henry student was beaten at Guerrant’s direction.

Guerrant — who reportedly was first introduced to the Rollin’ 30s while in prison for his 2007 murder conviction — “not surprisingly ... had a very troubled childhood,” Kowalczuk and Kenney wrote in a sentencing memorandum filed last week.

Guerrant’s late mother was a drug addict who spent part of his childhood in prison. At the age of 7, he began smoking marijuana. The habit led to daily use, which his attorneys say contributed to series of bad decisions that followed him through life.

As a seventh-grader, Guerrant was expelled from middle school for setting a fire. His disciplinary record included “loud outbursts in class, refusing to follow directions, fighting, stealing $118 from a teacher’s purse, calling teachers ‘crackheads,’ throwing a chair, and being talkative in class,” court records state.

His only job experience was two brief stints at fast food restaurants.

Perhaps his most significant accomplishment in life was establishing the Rollin’ 30s in Roanoke. Guerrant has a large gang tattoo on his stomach that he has displayed on Facebook, federal authorities say, and has made social media comments that indicate he was the gang’s undisputed leader.

A sentence of 37 years for the 31-year-old would be a downward variance from sentencing guidelines.

“While there are many aggravating factors in this case,” Kowalczuk and Kenney wrote, such a variance is justified in light of Guerrant’s “difficult and tragic childhood.”

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Laurence Hammack covers environmental issues, including the Mountain Valley Pipeline, and business and enterprise stories. He has been a reporter for The Roanoke Times for more than three decades.

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