John Dowd quit President Donald Trump’s legal team last month, frustrated by disagreements in strategy. None of that changed his belief in Trump’s innocence, though, or his desire to see the president free of special counsel Robert Mueller’s investigation. Yet even Dowd sounds baffled by just how the hiring of Rudy Giuliani will advance Trump’s legal cause. “I really don’t know,” Dowd says. “I know Rudy, I worked for him many years ago at the Department of Justice, and I knew him a little bit when he was mayor of New York City and United States attorney. I got a message that he wanted to talk to me, but I haven’t talked to him yet. I’ve never done a case with him. I’m not aware of him ever defending a case. So I don’t know what he’s going to do.”

Last year, Giuliani was involved in an unsuccessful attempt to broker a deal on behalf of a Turkish gold trader charged with violating sanctions against doing business with Iran. But his recent court appearances have been rare, and the simplest analysis may be the correct one: that Giuliani was the best Trump could do, after failing to hire more logical, seemingly better-qualified white-collar defense lawyers, including Ted Olson, Dan Webb, and Tom Buchanan. Giuliani is a marquee name, and has been a flagrantly vocal public advocate for Trump in the past, most notoriously by delivering a vein-popping speech attacking Hillary Clinton at the 2016 Republican National Convention.

Trump is more calculating than commonly understood, however. He hired Giuliani, the former head prosecutor at the Southern District of New York, shortly after the S.D.N.Y. raided the offices of Michael Cohen, the president’s personal lawyer. Perhaps Trump believes Giuliani, who touted his contacts in the New York office of the F.B.I. during the Clinton e-mail investigation, can work similar magic with his hometown prosecutors—even though Giuliani hasn’t worked in the S.D.N.Y. since January, 1989. “There are plenty of names I could give you of lawyers who are wired into that office,” another, more recent S.D.N.Y. alumnus says. “Rudy is not one of them.”

The Reverend Al Sharpton, a longtime antagonist of Giuliani’s and a wily practitioner in the use of publicity to move the criminal justice system, sees an extralegal ploy in the making. “Rudy worked in the highest levels of the Justice Department,” Sharpton says. “It gives him, in some areas, a credibility to take shots at Rosenstein, Mueller, and Comey. That’s the only thing that makes sense to me.”

“Rudy is not a young guy anymore, and he’s clearly lost a step.”

No matter the plan, Giuliani’s capacity to execute it is a subject of debate. Months ago, a former high-ranking New York City law-enforcement official asked me, out of the blue, what I knew about Giuliani’s “health.” Not much. But the chatter has intensified since Giuliani signed on with Trump’s legal team. Some sources recall a New York Post Page Six item from August, 2017, that described how Giuliani, 73, had been rushed to a hospital after falling and that included quotes from Giuliani and his third wife, Judith, strenuously explaining that the cause was a weak knee. Others point out that in early April, Judith Giuliani filed for divorce, and that Rudy seems to have recently spent a lot of time in Manhattan cigar bars. “Rudy is not a young guy anymore, and he’s clearly lost a step,” one New York Republican insider says. “Where the fuck did he go after the inauguration? He didn’t get what he wanted from Trump—to be secretary of state. The old Rudy would have been out on the talk shows. He’s rarely done that. Rudy wanted a way back in. With Rudy, it’s never about the best and the brightest—it’s, what’s in his best interest?”