Alex Spiro Objects!

On Wednesday morning, the attorney Alex Spiro followed his client, Mayor Eric Adams, into the lobby-level courtroom of Manhattan federal Judge Dale Ho.

It had been six days since the mayor was indicted, and Spiro had already launched an aggressive defense. At the Wednesday hearing, Spiro argued that it was the Justice Department, represented by the four prosecutors sitting nearby, who had done something wrong by leaking information about the indictment. He also claimed that prosecutors were being slow with sharing material in discovery and made the case for a trial sooner rather than later — as early as February. “I know how to try cases, and I will be ready for trial,” he said. “We expect the mayor to be acquitted, quickly.”

But the hearing did not quite go as planned for the defense attorney. Spiro fumbled an argument about the ballot certification for next year’s primary, and Judge Ho appeared skeptical the ballot would be affected much by the trial. The arguments about the alleged leaks devolved into whether Adams would take advantage of abstruse court rules that could have forced the government to move faster, all but erasing the prosecution’s advantage of extra time, if the argument succeeded. At one point, the government detailed at length the kinds of evidence it plans to lay out in a “likely” superseding indictment — including apparent allegations of witness tampering, new defendants, and issues with Adams’s cell phone — only for Spiro to interrupt. “I’m going to object to the continual 20-minute opening statement,” he said. Instead, Ho allowed prosecutors to continue.

Spiro is one of the city’s most familiar stock characters — a brawling, meticulously groomed, in-your-face attorney whose client list draws from the upper heights of the world’s wealthiest and most notorious. Adams, of course, is another kind of New York fixture: the made-for-the-tabloids mayor trailed by corruption allegations. The fact that they found each other amid Adams’s historic indictment for bribery and fraud is probably not surprising. Spiro has represented Jay-Z, Mick Jagger, and Alec Baldwin, all to success. But while Spiro’s confrontational style has brought him a book of clients that would be the envy of any defense attorney, the Adams case is proving to be wildly unpredictable, and it could humble lawyer and client alike.

“He’s got a lot of zealousness. For the clients he represents, he’s very tenacious, and he won’t give up,” says Daniel L. Brockett, the chair of Quinn Emanuel’s financial-litigation practice. “You know that if you’re going to trial against Alex that he’s going to have uncovered every potential angle, every potential stone, to make sure that he’s giving his client the best service possible. He’s a terrific lawyer, and he’s very tenacious, very, very hard working, and very much driven to win.”

Step one for any high-profile criminal-defense attorney is attacking the government’s allegations. Hours after U.S. Attorney Damian Williams laid out the 57-page indictment last Thursday, Spiro zeroed in on count five: bribery. According to prosecutors, when he was Brooklyn borough president in 2021, Adams pressured Fire Department officials to approve the opening of the brand-new Turkish Consulate, allegedly in exchange for airline and hotel perks he previously received — a supposedly cut-and-dry quid pro quo case. “This case isn’t even a real case. This is the airline-upgrade corruption case,” Spiro said during a press conference following Adams’s not-guilty plea. On Monday, Spiro fleshed out the argument for a different audience: the judge overseeing the case. The connection between the quid and the quo was not clear, Spiro argued. The upgrades were mere gratuities, not evidence of anything nefarious. The consulate wasn’t even in Brooklyn. “The indictment in this case alleges a ‘bribery’ scheme that does not meet the definition of bribery and indeed does not amount to a federal crime at all,” he wrote.

On paper, Spiro is the co-chair of the investigations, government enforcement, and white-collar defense practice at Quinn Emanuel Urquhart & Sullivan — the kind of firm you call if you’re a hedge-fund billionaire suing the IRS or up for a lifetime appointment on the Supreme Court. Spiro leads a staff of 100 in his Miami office, where he takes on about 50 cases at a time, according to a 2023 New Yorker profile. When Spiro is in the news, he’s usually standing next to one of his A-list celebrity clients. He has appeared in Kanye West’s texts and has served on the board of directors of the company Mike Bites, which makes Mike Tyson’s ear-shaped cannabis gummies. Then there are the billionaires. He is one of Elon Musk’s “hard-core streetfighter” attorneys and has represented Robert Kraft, the owner of the New England Patriots, who was once charged in a low-level prostitution offense. With Kraft and Baldwin, who was accused of manslaughter after fatally shooting a cinematographer on the set of the movie Rust, Spiro has proved his worth; he managed to get both charges dismissed.

In the legal world, Spiro is a celebrity in his own right. After a brief stint in the CIA, the Harvard Law School graduate started his career in the Manhattan District Attorney’s Office in 2008. It was an auspicious time for a young attorney. Robert Morgenthau’s 35-year stint as the DA was coming to an end, and the new boss, Cyrus Vance Jr., had an interest in bolder, more complex financial cases. Spiro, with a reputation for hardly sleeping, came prepared to bring cases quickly, demonstrating both a deep understanding of the law and a fine grasp of details, such as whether a local lab stored a particular piece of evidence. “Even if you had a front-row seat for it, it was never totally clear how he seemed to be doing as much as he was doing,” says one former assistant DA who worked with Spiro.

At the time, Spiro had a reputation as being exceptionally confident, even in an industry that is not usually lacking in egos. “If there was ever something people didn’t want to do, he was definitely the type of guy who volunteered to do it,” says David Moreno, another former ADA (Spiro also boxed at charity events for the DA’s office. “A pretty decent athlete,” Moreno says.) Spiro would try to build up his reputation by taking on difficult cases and stood out in the courtroom during trials. In closing arguments, like in the murder trial of Travis “Trav-Ice” Woods, he gave vivid, hard-boiled descriptions of the kinds of street crime that made for tabloid fodder. “Travis Woods is walking by a police officer who knows exactly who he is,” Spiro said then. “Ice is out there. He’s walking alone. He is out there with a purpose. He has one hand in his black hooded sweatshirt pocket, and that hand is on the murder weapon.”

In 2013, Spiro left the DA’s office to work on the other side as a defense attorney with Ben Brafman, who had arguably perfected the celebrity superlawyer persona with clients like Harvey Weinstein, Sean Combs, Martin Shkreli, and Nxvium sex cult leader Keith Raniere. (Brafman is now representing Deputy Mayor Phil Banks, an Adams ally, in a separate federal probe.) “They were a larger-than-life shop that had defended big-name celebrities,” says one of the former ADAs. “They were courtroom trial lawyers by reputation, and he obviously thrived there.” When Spiro joined Quinn Emanuel four years later, he was bringing in a book of new business that the firm wasn’t well known for defending: individual clients in criminal cases, Brockett says.

Take Jay-Z’s civil case against Roc-A-Fella Records co-founder Damon Dash. For years, the Brooklyn rapper has been fighting Dash over his stake in the legal entity that owns the rights to his debut album, Reasonable Doubt. That fight has spawned multiple lawsuits that seek to block Dash from selling his stake to anyone but Jay-Z. Natraj Bhushan, an attorney representing Dash, says that Spiro took an “aggressive approach.” In one instance, Bhushan says, Spiro wanted to question people involved in a long-dismissed sexual-assault case against Dash. “That’s the kind of crap that they would do.” Outside the court, he says, Spiro tones it down. “Some of these people are just dicks. They’re pompous assholes, right? They carry it from case to case. He’s just not that guy. He might have some kind of aura around him from the legal community, but I’ve found him to be professional.”

But Spiro’s aggression has also led to some embarrassing moments. In March, a lawyer representing a man suing Musk for defamation called Spiro “astonishingly unprofessional” for his conduct during a deposition and asked for the court to sanction him (the court declined). Bobby Shmurda, the Brooklyn rapper who pleaded guilty to conspiracy and weapons-possession charges in 2016, accused Spiro of having “forced me to take this plea,” which Spiro denied. In 2022, when Musk tried to back out of his $44 billion purchase of Twitter, Spiro led a quixotic, legally questionable crusade that a Delaware judge called “absurdly broad,” and that opened up Musk to embarrassing claims against him and his closest allies in Silicon Valley. Later that year, the New York Times reported that Spiro and Musk had a falling out over personnel decisions at Twitter, and he was no longer working at the social-media company, even though he continued to represent him personally. Still, his track record — particularly in criminal cases — shows that defendants would probably be better off with Spiro as their lawyer. (Through his assistant, Spiro declined to be interviewed.)

Spiro, though, isn’t the only aggressive lawyer in town, and the Adams case is sure to test him. Hagan Scotten, a prosecutor for the Southern District of New York, took advantage of his time at the podium on Wednesday to attack Spiro’s defense that the Adams case is all about airline perks, alleging that the mayor’s upgrades were requested before he traveled and that the day-of upgrades were a ruse. He also said that potential witnesses approached by the FBI were later told not to be truthful to investigators. Spiro, for his part, complained about the wide range of subpoenas to get information on “every interaction that Mayor Adams has had with immigrant communities. I don’t know why it’s so interesting to them.”

Spiro has been representing Adams since at least April in a sexual-assault lawsuit stemming from accusations going back to 1993, which Adams denies. (On Wednesday, Spiro asked a judge to step down from representing him in that case to avoid a conflict of interest). Exonerating Adams in the federal case, though, will be a heavy lift for Spiro, even if he’s already seeing results in the court of public opinion. The editorial boards of the New York Post and Daily News have echoed some of Spiro’s arguments in questioning the seriousness of the case and backing off on calls to resign. But the charges against the mayor are not, in fact, limited to a few airline upgrades but extend to a vast network of allegedly illegal straw donations from foreign nationals that the government says resulted in an additional $10 million in public funding — which it says amounts to fraud against the city. In his filing, Spiro also acknowledged that the Fire Department official that Adams had reached out to about the Turkish Consulate’s safety issues had previously asked about retaining his job in a future Adams administration — after he won the primary and appeared to be on the glide path to winning the election that fall.

Still, Adams has so far refused to step down, even in the face of withering criticism from across the political spectrum and conditional support from Governor Kathy Hochul, who has the power to remove him. In public appearances, he has been sticking with the argument that the airline upgrades fell short of bribery. On Tuesday, when a reporter asked him how he found the service on Turkish Airlines, he laughed. “I love that question,” Adams said. “Great service. Great service.”