A contractor for U.S. Immigration and Customs Enforcement is under investigation by his employer for posting bail in March to free a member of the right-wing men's fraternity the Proud Boys from the Multnomah County Jail.

The Proud Boy is Donovan Flippo. He was indicted Feb. 27 and booked into the Multnomah County jail March 12 on felony assault and misdemeanor assault charges for allegedly attacking a man on a Portland sidewalk last June. Hours after Flippo, 23, was transferred from a jail in Vancouver, Wash., to the Multnomah County Jail, a man from Washington state paid the $750 bail.

Court records show that man was Nicholas Carefelle, 37, who works for a private prison and immigration detention contractor called the GEO Group.

WW attempted to contact Carefelle directly and through his friends, his attorney and his employer. Carefelle did not return multiple calls, emails and texts asking for comment on this story.

A GEO Group spokesman confirmed Carefelle works for the company in Portland. One day after WW contacted GEO about Carefelle's engagement with far-right groups, the company says it launched a probe.

"Our company has launched an internal investigation into this matter and will take appropriate actions following its conclusion," says Pablo Paez, executive vice president of corporate relations.

ICE directed questions about Carefelle's actions to GEO Group.

"U.S. Immigration and Customs Enforcement holds those working within our facilities to the highest standards of professional conduct," Tanya Roman, a spokeswoman for the federal agency, said in a statement. "The incident in question does not involve a federal employee. Please contact The Geo Group for additional information."

Carefelle is a private citizen, and his off-duty speech is protected by the First Amendment.

But he performs work for the federal government under contracts with ICE. The GEO Group has access to government information about immigrants and access to immigrant detainees through detention centers, probation services, and transport operations. GEO Group, which specializes in incarceration, runs "residential centers," or detention centers, where ICE houses detainees awaiting hearings in immigration court.

GEO did not specify what job duties Carefelle performs, and it is unclear whether he works directly with detainees. He has firearms certifications from the Washington State Criminal Justice Training Commission issued in 2016, 2017 and 2018.

The Aug. 4 showing was one of the largest gatherings of Proud Boys in Portland. The men’s fraternity, which wears gold-trimmed polo shirts, has been labeled a hate group by some watchdogs. (Liz Allan)
The Aug. 4 showing was one of the largest gatherings of Proud Boys in Portland. The men’s fraternity, which wears gold-trimmed polo shirts, has been labeled a hate group by some watchdogs. (Liz Allan)

An advocacy nonprofit says the association between an ICE contractor and the Proud Boys is troubling.

"Western States Center is concerned to learn that a Portland-based ICE contractor provided bail to a known member of a group that has used political violence to terrorize vulnerable communities and undermine democratic institutions across the Northwest," says Amy Herzfeld-Copple, deputy director of programs and strategic initiatives. "We encourage local and state officials to immediately open up investigations to ascertain if GEO Group is intentionally or unintentionally supporting violent paramilitary activity in the city of Portland."

Flippo was behind bars because he allegedly attacked a Portland man named Tim Ledwith last June with his fellow Proud Boy, Tusitala Toese, on a Northeast Portland sidewalk after Ledwith cursed at the Proud Boys and flipped them off.

Flippo is set to appear in Multnomah County Circuit Court on May 17.

Flippo is a member of the Proud Boys, a far-right fraternity that bills itself as a social club for men, calls its members "Western chauvinists," and has ties to the alt-right movement in American politics. The group's founder, Gavin McInnes, has voiced opposition to immigration. The group has regularly marched in the streets of Portland and brawled with masked antifascists.

Carafelle has interacted with left-wing protesters on a previous occasion.

Last summer, protesters blocked the entrances and exits to a federal building in Southwest Portland, temporarily shutting down ICE operations there for several days.

Carefelle tricked protesters into allowing him to retrieve his truck parked inside the lot near a federal building in southwest Portland where U.S. Immigration and Customs Enforcement and GEO Group employees work.

Ledwith, the alleged victim in the assault that put Flippo in jail, says he was at the protest camp last June when protesters blocked ICE employees from driving their cars home. He says he remembers trucks driving past the camp and suspected Proud Boys had been circling the protest.

"I was there that night at Occupy ICE," Ledwith says. "I stuck around because everyone was hysterical saying that the Proud Boys were there. There were these trucks driving by that seemed to be them or some adjacent Patriot guys."

Carefelle dispelled the tension by telling the protesters that he was trying to retrieve a truck for his friend, who he claimed was a Tesla employee.

"I made up a story," Carefelle told WW at the time. "I told them that we were there for a friend who was a Tesla employee whose vehicle was trapped in the back field and that our friend was real spooked and scared by all the stuff going on. A lie is what got my truck back to me."

The protesters believed the tall tale and let him get into his Toyota pickup and drive it out of the lot.

Carefelle has interacted with several self-identified members of the Proud Boys, as revealed in public records and social media posts obtained by WW.

After Toese's arrest for assault, Carefelle donated $50 to the violent right-wing brawler.

Toese, a 6-foot-6 Samoan man, has been arrested three times in Portland for violent attacks at protests and was convicted of harassment last January for punching a masked protester in the face unprovoked. A grand jury voted to indict Toese on a felony assault charge in March, but Toese fled to his hometown in American Samoa before he could be arrested.

A Facebook page under the moniker "John N. Wick" used Carefelle's legal name in the URL and said he worked at Northwest Detention Center, an ICE facility in Tacoma, Wash.

That Facebook page also had "liked" several pages linked to the far-right and anti-government groups like the Oath Keepers and the Press Guard Page, a "free speech" group connected to the pacific northwest chapter of the Three Percenters.

After WW began calling people connected to Carefelle, the Facebook page disappeared.

Screenshot of Nicholas Carefelle’s Facebook page.
Screenshot of Nicholas Carefelle’s Facebook page.
Screenshot of Carefelle’s Facebook “Likes”.
Screenshot of Carefelle’s Facebook “Likes”.