“I’m the guy who protects the president and the family. I’m the guy who would take a bullet for the president,” Michael Cohen, longtime personal lawyer to Donald Trump, told my colleague Emily Jane Fox last September, months before his involvement in Robert Mueller’s Russia investigation moved from a passing mention in the Steele dossier to the inside of a Manhattan courtroom. Indeed, Cohen’s loyalty to the Trumps spans more than a decade, from his time working for the Trump Organization, to his role as Trump’s fixer and self-declared legal pit bull, hounding reporters (“tread very fucking lightly, because what I’m going to do to you is going to be fucking disgusting”) and disappearing claims of Trump’s alleged affairs (or not). That loyalty is now being put to the test, and Trump’s allies are beginning to worry. Last week, Cohen’s office, apartment, and hotel room were raided by the F.B.I. on a tip from Mueller’s team, dragging Cohen into a parallel investigation by the U.S. Attorney of the Southern District of New York. But when he appeared on CNN to discuss the raid, the normally combative Cohen responded by calling the agents who searched and seized his property “extremely professional, courteous and respectful.” Alarms immediately went off in Trumpworld. “When anybody is faced with spending a long time in jail, they start to re-evaluate their priorities, and cooperation can’t be ruled out,” one Trump ally who knows Cohen told Politico.

While Cohen is reportedly being probed, among other things, for payments to two women in 2016 who alleged affairs with Trump—a potential campaign finance violation—lawyers familiar with Mueller’s investigation seem to assume that the feds’ case is much larger. “I think for two years or four years or five years, Michael Cohen would be a stand-up guy. I think he’d tell them go piss up a rope. But depending on dollars involved, which can be a big driver, or if they look at him and say it’s not two to four years, it’s 18 to 22, then how loyal is he?” a defense lawyer representing another senior Trump aide in the Mueller investigation told the outlet. “Is he two years loyal? Is he 10 years loyal? Is he 15 years loyal?”

The fascinating thing about the way Trump’s own allies describe the Cohen predicament is that they seem to assume that both men are guilty of serious crimes. “Michael will never stand up [for you]” if he faces charges, former prosecutor Jay Goldberg, who represented Trump in the 1990s and early 2000s, told The Wall Street Journal in an interview. Cohen could possibly wear a wire to their meetings, he warned Trump when the president reached out for his advice about what Cohen might do. “The mob was broken by Sammy ‘The Bull’ Gravano caving in out of the prospect of a jail sentence,” Goldberg recalled, suggesting that Cohen might cut a deal with prosecutors. On a scale of 100 to 1, where 100 is protecting Trump completely, Goldberg told the president that Cohen “isn’t even a 1.”

Again, the issue raised by Goldberg—a former Trump lawyer with intimate knowledge of Trump’s business empire—is not whether Trump or Cohen committed any crimes, but whether Cohen will roll over on his boss when prosecutors turn up the heat. Even Anthony Scaramucci, the irrepressible Trump cheerleader, seemed to accept that premise when he was asked Wednesday on MSNBC whether “there’s any chance [Cohen] would end up cooperating.” Scaramucci looked unsure: “People who you think are loyal to you end up not to be loyal to you,” he responded carefully, before noting that Cohen had always struck him as a “very loyal” person. “If you said to me, and I had to flip a coin, is he going to turn on President Trump or turn on other people, I would say adamantly, no.”