Welcome back to the Big Law Business column. I’m Roy Strom, and with news of Weil Gotshal & Manges’ stunning collapse captivating the legal world, I take a special look at the unique personal relationship that both defined its successes and helped bring on its demise. Sign up for Business & Practice, a free morning newsletter from Bloomberg Law.

A law firm, even one with 1,200 lawyers, is simply a collection of relationships: partners deciding to work together. It thrives when those relationships are strong. And it can die if they wither.

At Weil Gotshal & Manges, there was no relationship more important than that between Mike Aiello, its highest paid partner and most prodigious business generator, and Barry Wolf, its longtime executive partner. Their story is the story of Weil’s final decade. Their relationship dictated the firm’s strategy and decisions. It decided who stayed at the firm and who left. And when it shattered, the firm did too.

Interviews with more than a dozen people, most of whom held leadership positions at Weil, point out how the complex relationship between Wolf and Aiello—and key misunderstandings between the pair—set the stage for the firm’s implosion within weeks of Aiello’s announced departure to Cravath. The sources were allowed to speak without being identified in order to describe a dynamic that many of them are still grappling to process. Some described being asked in recent days whether Weil’s fall shocked them.

“I have been telling people this is coming for years,” one said.

Weil had been falling behind its competitors gradually but consistently over the almost two decades that Wolf and Aiello practiced together. Its revenue growth was half the annualized rate of its competitors from 2008 to 2025, according to data from The American Lawyer and Citi’s law firm banking group.

But Aiello’s status as the firm’s largest business generator meant firm leaders were unwilling to part ways with him—even as he became a source of contention at board meetings over his unwillingness to invest in new practice areas. That meant the task of dealing with Aiello fell to Wolf—the man Aiello pledged his loyalty to for so long.

The pair were bound in many ways, including a provision Wolf negotiated when he became the firm’s leader that he would always be paid the same as the firm’s highest paid partner. In recent years, that was Aiello. That dynamic complicated people’s view of their relationship and their respective jobs—Wolf’s only role was to run the firm; Aiello was tasked with client matters.

As Wolf became preoccupied with managing Aiello, the law firm that was proud to be glued together by a family dynamic stumbled and tripped headfirst into a commercial-minded business model adopted by rivals who devoured it. It is nearly impossible to answer the inevitable question: Did Wolf fail at his job, or did Aiello neutralize effectively the only boss he ever had?

“I’d hate to admit that parts of that are true, but we were largely partners and people felt a certain allegiance to a certain degree,” one former partner said. “And that came a little bit from Barry and Mike.”

A prominent public company dealmaker, Aiello joined Weil from Dewey Ballantine in 2008—four years before that firm collapsed following a merger with LeBoeuf, Lamb, and three years before Wolf became Weil’s leader. Wolf recruited Aiello to the firm through a previous relationship the chair had with Aiello’s brother, John.

When Wolf described Aiello in a May interview with Bloomberg Law as his “closest friend in the firm,” it was a strange choice of words. The pair weren’t necessarily social friends, and the leaders of today’s largest law firms don’t typically discuss their partners being their closest friends anyway. They talk about those lawyers being excellent, superb, the best talent for the firm’s clients.

This was Wolf defending his family, even if his relationship with his closest friend “in the firm” was on the ropes.

“The strength of their relationship was in the loyalty to each other,” a former member of the management committee said.

Partner loyalty to Weil carried a cost and the firm didn’t pay as well as some of its closest rivals. Its partners earned more than $5 million on average last year, lower than the $8 million to $10 million at competitors. Still, many partners were happy with the trade for quite some time, even as the industry grew to be defined by lateral jumping between firms.

Aiello and Wolf were somewhat ill-suited for those recruiting wars, viewing the business through their lens of loyalty. Why would you hire a partner who was proving their disloyalty by leaving their firm?

Barry Wolf Photo: Weil Gotshal & Manges

Instead, they focused on bringing back lawyers who had left Weil once before. They were proving how special Weil was by returning. Wolf called Aiello “the original boomerang.” He had returned to Weil at Wolf’s urging amid Dewey’s merger talks with Orrick in 2008, a move that the American Lawyer reported contemporaneously was a key factor in those discussions’ failure.

Aiello disliked lateral partner hiring so much that when a rival firm recruited a handful of its lawyers, a powerful partner at that firm was told Aiello was trying to get his phone number. The partner believed Aiello was going to dress him down, even if the call never came in the end. Standard business practice when losing a partner in Big Law is to shrug and say, “Best of luck in your future endeavors.”

“There is a humane side to both of them,” said one former partner. “But the lesson to me is humans are not perfect. We’re all imperfect. We all have our faults. And we have to forgive each other.”

Families are complicated. They can be loyal to a fault, sticking together through trauma, abuse, or neglect. And some describe Aiello and Wolf’s dynamic inflicting all three of those things on the people around them.

A common dilemma involved partners asking Wolf to help convince Aiello to do something, and Wolf struggling to enact the change even though he was the top leader.

One management committee member asked Wolf to take him off the board after Aiello shouted at him during his very first meeting; Wolf convinced the partner to stay. Another partner said he anticipated being punished when he advanced a business idea intended to help the firm grow. Wolf demurred, telling the partner it needed Aiello’s blessing first (which it didn’t get.)

Inevitably, the dynamic wasn’t going to last forever—and Aiello often said how it would end.

He was prone to saying that he wouldn’t stay at Weil if Wolf wasn’t its chair. And by the end of 2027, Wolf was going to hit the firm’s mandatory retirement age.

As that time approached, it began to matter how seriously people took Aiello. Some perceived what he said as a threat. Others viewed it as a more straightforward vote of confidence in Wolf. Or maybe he was saying he would have left by that point had somebody else been chosen besides Wolf to begin with. Different people took it differently.

And so, Wolf and Aiello’s relationship set up whoever was to take Wolf’s place with the task of replacing a leader of 15 years and the firm’s most important partner all at the exact same time. And do it on or around Jan. 1, the most precarious time in a law firm’s existence, just weeks before its partners get their biggest paychecks of the year and feel most free to be courted by new suitors.

I asked one person familiar with the firm’s leadership dynamics who should have taken the job of replacing Wolf. The reply: Nobody. And that might help explain why the partner picked for the job, Ramona Nee, told a small group of partners that she wouldn’t take it—two months before Wolf told the firm’s partners on a Zoom call that the best path forward was an orderly dissolution. (Nee is now in discussions to join Kirkland & Ellis.)

Michael Aiello was called Weil’s “original boomerang” partner after returning to the firm in 2008 and taking control of the corporate department.

By that point, there was more than a succession problem. Wolf and Aiello’s relationship was strained, a result of the long-running dispute that their partners had brought to their feet over the future direction of the firm. Was Weil going to adapt to the modern Big Law era and invest in its private equity practice, as many of its partners wanted? Or was Wolf going to side with Aiello’s view of the future? Aiello wanted to stick to the firm’s public company M&A practice and perhaps reposition itself by growing smaller.

Aiello appeared at times to back the idea of growth. Two sources said he approached, on his own, the law firm Vinson & Elkins, though the discussions went no further than a couple of meetings.

Wolf was in the middle of it all, and it’s unclear if he truly made a decision.

The run on the bank at Weil was perverse in the sense that it was started by some of the firm’s highest paid partners and its harshest impacts will be felt by its most vulnerable employees. And that’s true. But the wealthiest members of the firm, by virtue of their own success that the firm relied upon, had the closest proximity to the Wolf-Aiello alliance, to where they may have understood it in ways that differed even from the two men themselves. Many of them seemed to sense it would be the firm’s demise. Some had predicted it for years.

As of September, the two seemed to still have a misunderstanding whether Aiello had agreed to stay on past Wolf’s retirement. Sources familiar with the matter say the two spoke on Sept. 8. Wolf was asking Aiello to commit to staying as the firm recovered from recent departures. It is unclear the two men came to an understanding.

What is known is that on Sept. 10, Aiello’s team walked into Wolf’s office and submitted their resignations, including on Aiello’s behalf. Their breakup wasn’t face-to-face. It was over text.

Aiello chose Cravath, one reason being that it was willing to take his entire team, a display of the personal loyalty some saw as the best in him. Still, others viewed his decision as an ultimate betrayal.

The timing couldn’t have been worse. Coupled with the major departures from the firm’s private equity practice, Weil’s PE service capabilities by the time Aiello quit were severely diminished. Neither of the top lawyers at two of the firm’s most important clients have responded to questions about whether they would have kept working with Weil, though there are rumors they would not.

In the end, Weil didn’t invest in its private equity practice, and with Aiello’s pending departure, it would no longer have a leading public company M&A practice, either. With Nee opting out, it had nobody lined up to run the firm. A partner compensation haircut was coming, and the place would look nothing like it used to. Who could guarantee they would stay for that, amid better options?

It had been financially healthy. But it was no longer. The partners decided not to continue working together.

When the end came, Wolf delivered the news from the head of a table littered with water bottles and electrical plugs. He and members of the management committee had been engaged for days, practically nonstop, with advisers from Davis Polk & Wardwell and others.

Virtually every person in the room had cried that day, including one who had recently returned from burying a parent. To the very end, they were seeking a path for the firm’s future. None could be found. The partners couldn’t trust each other to stay loyal to the firm.

Aiello had been in a Delaware courtroom on Wednesday morning, working on client matters he promised to finish up. He wasn’t in the room when the end was announced.

The two haven’t spoken. About any of it.