On The Merits

Sidley Austin LLP crossed $3.74 billion in revenue last year and has its sights set on $4 billion — but according to its top leader, the number is a byproduct, not the goal. The real question is whether the firm is built for what comes next. Today on On the Merits: Yvette Ostolaza, chair of Sidley's management committee, sits down with Bloomberg Law reporter Meghan Tribe to discuss strategic lateral hiring, formal integration plans, and a willingness to pull back from practices and geographies that aren't growing. "There are no sacred cows," Ostolaza said. "We need to continue to evaluate how the industry is changing." She also weighed in on how Sidley is treating AI: not as a pilot project, but as core leadership infrastructure deployed across the firm with dedicated governance, training, and practice-group liaisons. "It doesn't replace judgment, it sharpens it," Ostolaza said.

For a long time, the top dozen or so law schools in US News & World Report's annual rankings stayed remarkably consistent, with Yale for example holding the top spot every year since the rankings debuted in 1990. But not this year. Yale is now no longer at the very top of the highly influential rankings, which were unveiled earlier this week, having slid down to number two. While this may seem insignificant, Bloomberg Law columnist David Lat said even dropping one spot can tangibly affect a law school's brand. Lat spoke about this with Bloomberg Law editor Jessie Kokrda Kamens for our podcast, On The Merits. He said recent changes in the methodology for compiling these rankings means we should expect more movement in and out of the top spots in years to come. Lat also talks about why the rankings matter for Big Law talent recruitment and beyond. Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

The chair of law firm Polsinelli says he doesn't want his attorneys—and especially not his junior attorneys—to use AI legal tools grudgingly. But the firm will not be giving associates billable-hour credit for learning how to use the technology. "They need to be very, very good at utilizing these tools and investing in themselves," Chase Simmons said on Bloomberg Law's podcast, On The Merits. "If you need motivation to learn how to use AI in your career right now, we probably have other things that we should be concerned about with you." "This should just be every day you wake up and have breakfast and think about how to incorporate this into your career," Simmons added. Simmons, who leads one of the fastest growing firms in the country, talked about how Polsinelli is adopting AI across the firm. He also explained Polsinelli's focus on being a "daily and weekly law firm" for its clients and discussed his views on the Trump administration's attacks on the legal industry. Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

The Trump administration surprised everyone last week when it first dropped an appeal in its fight against four law firms and then, less than 24 hours later, reversed itself and declared the case to be back on. The White House and Justice Department have yet to explain what prompted the dizzying two-day stretch. Late last week, a DOJ lawyer instead pressed an appeals court to overturn four separate rulings striking down Trump's executive orders against the firms last year. The about-face has highlighted questions about the legal rationale behind Trump's orders, targeting firms over ties to lawyers and causes the president sees as threats to his administration. But even if Trump ends up losing the appeal, he's already gained a significant amount of leverage from the legal industry in hard-to-quantify ways, according to Bloomberg Law reporters Meghan Tribe and Justin Henry. On this episode of our podcast, On The Merits, they speak with host Jessie Kokrda Kamens about the chaotic events of last week and where the president's battles against the legal industry may be heading next. Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

Large law firms are going all in on the nationwide data center build out—nevermind that lurking AI bubble. On today's episode of our podcast, On The Merits, we hear from Bloomberg Law reporter Roy Strom about several examples of law firms deploying multidisciplinary practice groups to solve complex problems for data center builders. Roy also talks about why it may not pay for firms to approach the data center boom cautiously. "If this work goes away, the law firms will struggle, there'll be some partners who have a lot of time on their hands," he said, "but the bigger risk to the law firms right now is probably missing out on a sort of once-in-a-generation extravaganza." Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

The future lawyers of America were taking the LSAT this weekend. But, by the time they get their JDs in a few years, law firms may have replaced many of their entry-level associate jobs with AI. That's a fear Mike Spivey hears a lot about these days. Spivey is a former law school administrator who is now an admissions consultant working with schools and prospective students. He says law school applications for the class of 2029 are spiking right now—even though AI may totally transform the legal industry by the time they graduate. Law schools are asking themselves "'Are we admitting people and bringing in large class sizes who, in three to four years, we're setting up to be in great debt? Are we going to have these debt-ridden people without jobs?'" Spivey said on our podcast, On The Merits. "That's the tension." Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

There was a time when elite Wall Street firms such as Cravath or Wachtell seemed to rise above the lateral tug-of-war among other firms. That doesn't appear to be the case any longer, with a handful of partners from both of these firms announcing their departures for competitors last month. "I don't think these are one-offs," legal recruiter Sabina Lippman said. "It's a pattern." Firms like these will need to adjust their mindsets—and perhaps their pay structures as well—to stay at the top, according to two New York-based legal recruiters who spoke on our podcast, On The Merits. Lippman, co-founder and global managing partner at CenterPeak, and Todd Merkin, executive director of Wegman Partners, spoke to Bloomberg Law's Jessie Kokrda Kamens about this newest phase of what Lippman calls "the talent wars." Merkin said that these firms have "really been focused on talent retention, and not so much on talent acquisition. So they're a little bit behind as far as that goes." Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

The trial of Tom Goldstein, the elite Supreme Court advocate and co-founder of SCOTUSBlog who was charged with criminal tax evasion after years of playing ultra-high-stakes poker games, continues this week in Maryland. Bloomberg Law reporter Holly Barker, who's there covering the proceedings, joins us to talk about it on our podcast, On The Merits. Barker lays out what Goldstein's defense will likely be and why his status as an elite lawyer could make it harder for that defense to succeed. She also talks about why some poker-loving Hollywood celebrities may be called to the stand to testify against Goldstein. Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

There's never a good time for a law firm to see one of its most prominent partners leave and take several attorneys with him. But this is especially bad timing for Bernstein Litowitz Berger & Grossmann. The firm specializes in representing shareholders suing companies in Delaware, the incorporation capital of the world. But ever since Elon Musk reincorporated Tesla outside the state in response to a lawsuit over his pay package—a lawsuit Bernstein Litowitz led—the state has changed its laws to make it harder for shareholder plaintiffs to succeed. In this episode of our podcast, On The Merits, Bloomberg Law reporters Jennifer Kay and Tatyana Monnay talk about the unusual bitterness Bernstein Litowitz expressed to its departing colleague after he exited the firm. They also talk about why, after the seismic corporate law changes of 2025, it may no longer be as lucrative as it once was to represent shareholders in Delaware. Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

New York's oldest law firm answered the outstanding question surrounding its ability to remain independent with a resounding no when it announced a merger with Hogan Lovells last week. As Bloomberg Law reporter Meghan Tribe tells it, Cadwalader Wickersham & Taft had been in a gradual decline since the 2008 global financial crisis. It also failed to adapt to the new reality of the legal industry in which lateral hiring is not just commonplace but necessary for a firm's survival, she said. On this episode of our podcast, On The Merits, Tribe gets into what transpired that forced the more than 200-year-old firm to put itself up for sale, and also what made Hogan leap at the chance to merge with Cadwalader. Additionally, Tribe talks about what the tie-up could mean for the pro bono deal Cadwalader struck with the Trump administration earlier this year. Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

Now is the time of year when many law firms pressure their attorneys to get their clients to pay bills before the end of the year. It's something that clients loathe just as much as their attorneys, according to today's guest on our podcast, On The Merits. Eric Dodson Greenberg, the general counsel of Cox Media Group, said the lawyer-client relationship can suffer when firms bill too aggressively and not thoughtfully enough—a problem made worse by the move toward automated billing. He said he's lost some trust in certain outside firms he's worked with when they send him surprise invoices. "What law firms have done is divorced the billing process from the exercise of judgment," he told Bloomberg Law editor Jessie Kokrda Kamens. "Law firms often prioritize that last push in December to get all that they can and not really focus on 'What's the relationship we inherit on January 1st?'" Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

It's been a difficult year for Brad Karp, chair of Wall Street law firm Paul Weiss. In January he suffered a heart attack and then, a few months later, he chose to strike a pro bono deal with the Trump administration to stave off a punitive executive order. In a recent speech at a gala event in New York, Karp said the latter was more painful than the former. But during that speech, a fellow attorney stood up and heckled him—an indication of how raw feelings within the legal industry still are over the pro bono deals. Bloomberg Law reporter Mike Vilensky was at the event and saw all of this go down. He joins our podcast, On The Merits, to talk about who shouted at Karp, why, and what the two had to say to each other after the event concluded. Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

The top lawyers at the largest publicly traded companies in America are being asked to wear many hats at once—and also getting paid handsomely to do so. That's the takeaway from a recent story by Bloomberg Law senior reporters Brian Baxter and Andrew Ramonas, who crunched data from SEC filings of S&P 500 companies and found out how much these attorneys are making. Alphabet's J. Kent Walker Jr. leads the list with a total compensation package exceeding $30 million. On this episode of our podcast, On The Merits, Baxter and Ramonas talk about who these highly paid executives are, the new responsibilities they have, and why they don't always hold the titles of "general counsel" or "chief legal officer" at their respective companies. Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.