Following last month’s release of Legal 500’s first US city elite rankings, Legal Business checked in with the newly ranked Chicago lawyers to learn more about the city’s legal market from the perspective of top regional and national firms.
The new rankings recognise a total of 63 lawyers from 37 firms – 20 of which were not previously ranked by Legal 500 in any category. Six lawyers from four firms were ranked in tier 1 for commercial disputes, with four lawyers from four firms in tier 1 for corporate and M&A.
The two firms with the most top-ranked lawyers are Bartlit Beck and Goldman Ismail Tomaselli Brennan & Baum, each with two lawyers recognised in disputes, and Neal, Garber & Eisenberg with two in corporate and M&A.
Tier 1 ranked lawyers
| Lawyer | Firm | Ranking |
|---|---|---|
| Rebecca Bacon | Bartlit Beck | Commercial disputes |
| Sean Gallagher | Bartlit Beck | Commercial disputes |
| Tarek Ismail | Goldman Ismail Tomaselli Brennan & Baum | Commercial disputes |
| Shayna Cook | Goldman Ismail Tomaselli Brennan & Baum | Commercial disputes |
| Leonard Gail | Massey & Gail | Commercial disputes |
| Steven Blonder | Much Shelist | Commercial disputes |
| Ethan Rii | Ice Miller | Corporate and M&A |
| Cristina DeMento | Neal, Gerber & Eisenberg | Corporate and M&A |
| Michael Gray | Neal, Gerber & Eisenberg | Corporate and M&A |
| Frank Chaiken | Thompson Hine | Corporate and M&A |
| Joseph Kye | Vedder Price | Corporate and M&A |
The firm with the most rankings is Much Shelist, with a total of five across both practices. Five other firms had three rankings or more: Barack Ferrazzano Kirschbaum & Nagelberg (BFKN), Benesch, Goldman Ismail, Shook Hardy & Bacon, and Thompson Coburn.
Firms with most ranked lawyers
| Firm | Total rankings | Breakdown |
|---|---|---|
| Much Shelist | Five | Three disputes, two M&A |
| BFKN | Three | Two disputes, one M&A |
| Benesch | Three | Two disputes, one M&A |
| Goldman Ismail | Three | Three disputes |
| Shook Hardy & Bacon | Three | Three disputes |
| Thompson Coburn | Three | Two disputes, one M&A |
‘Making complex ideas convincing’ – surveying the city legal market
Bartlit Beck and Goldman Ismail are two examples of a prominent feature of the Chicago market: boutiques spun off from larger shops to deliver a more tailored offering.
Bartlit Beck was founded in 1993 in Chicago and Denver by Fred Bartlit Jr, Philip Beck, Sidney Herman, James Palenchar, Don Scott, and Mark Ferguson, who all left Kirkland & Ellis along with 12 other lawyers.
Goldman Ismail, meanwhile, was established in 2009 by Bartlit Beck partners Andy Goldman, Tarek Ismail, and Ken Baum in Chicago, and legacy Fulbright & Jaworski partners Sean Brennan and Joe Tomaselli in Dallas.
Each firm focuses exclusively on litigation, and each touts its particular expertise in taking cases to trial. Each runs a tight ship – Bartlit Beck has 89 lawyers, 72 of which are partners, while Goldman Ismail has a total of 39, 19 of which are partners (according to each firm’s website).
Each also makes its rejection of billable hours a key part of its pitch to clients, with Bartlit Beck offering success-based fees and Goldman Ismail exclusively using alternative fee arrangements (AFAs) with a variety of structures.
Lenny Gail (pictured), now ranked in tier 1 for commercial disputes, followed a similar path when he set up Massey & Gail with Jonathan Massey in 2008, with experience as an associate at Kirkland (1989-93) and at Bartlit Beck (1993-2000), where he made partner.

‘We’re a central casting high-end litigation boutique in the national market’, he says of his firm. ‘That sort of firm is basically becoming extinct because of two things. One, clients increasingly focus on specialisation and not trial skills; if clients have an antitrust case that won’t go to trial, they increasingly go to an antitrust specialist. We’re not like that. We specialise in making otherwise complex ideas convincing to a court or jury.
‘The second is that far fewer cases go to trial. That’s because, for a case to warrant the fees these big firms charge, the amount in controversy has to be so great that to take it to trial is to roll the dice on a corporate bankruptcy. Clients don’t want to do that – and they shouldn’t! The result is that the most big money cases don’t go to trial.’
This leaves a niche for a firm like Massey & Gail to operate at the top of the Chicago market and in the wider national market, even in an atmosphere of pervasive consolidation.
In non-contentious work, however, says Gail: ‘The story in Chicago is no different than in most of American law: most boutiques are being swallowed up.’
‘We’re a central casting high-end litigation boutique in the national market. That sort of firm is basically becoming extinct’ – Lenny Gail, Massey & Gail
David Morris, corporate and securities group chair at Fox Swibel, concurs: ‘A lot of firms that are Fox Swibel’s size have merged into regional and national firms. There’s been a lot of consolidation in the industry.’
Fox Swibel was founded in 2000, and brands itself as a ‘big law boutique’. In Morris’s words, ‘We compete with the firms where we were trained as a value proposition by providing sophisticated legal services on a cost-effective basis.’
Chicago is an attractive destination for expanding firms for a number of reasons. McDonald Hopkins Chicago managing member Marc Carmel (pictured) explains: ‘Not only is Chicago a very big city, but it’s also the only really large city that’s close to a large portion of the country.’

This, he argues, makes it an attractive hub for flows of capital from the coasts to the interior. ‘There’s a lot of money in Chicago, and while there’s more on both the East Coast and the West Coast, a lot of that is invested into businesses in the Midwest. A lot of our clients are investing in businesses that we’re geographically closer to than they are. Obviously technological advances mean we don’t need to be on site at all times, but it helps to have experience in and knowledge of those markets.’
He also points to the city’s deep talent pool – a function in part of its top universities and law schools.
It is also, he notes, relatively affordable: ‘It’s much less expensive to run an office here than in Los Angeles or New York.’ Even if lawyer remuneration is similar, real estate and staffing costs are lower.
All this makes the Windy City attractive to not just international firms, but regional and national ones. Carmel’s own firm opened first in Columbus, Ohio in 2003, and expanded into Chicago in 2007 when it merged with Harris Kessler & Goldstein.
‘It’s ensured that we were productive and profitable from day one’, says Carmel. ‘The benefit of acquiring an existing office over making individual hires is that you know the existing platform can work.’
‘Not only is Chicago a very big city, but it’s also the only really large city that’s close to a large portion of the country’ – Marc Carmel, McDonald Hopkins
Thompson Coburn entered the Chicago market in the same year through a merger with Fagel Haber. ‘Chicago is a very competitive legal market’, says Chicago managing partner Katriina McGuire (pictured). ‘Client relationships run very deep, and it’s difficult to establish brand recognition if you’re just planting a flag of your own.’

Smaller headcounts can help regional and national firms attract laterals. ‘A lot of the larger firms don’t really encourage attorneys to build a book of business’, says one partner at a Chicago firm. ‘They have a small number of rainmakers at the top feeding everyone below them. A lot of lawyers come out of law school and go to a big firm because that was always what you did. But, if you do that, you might wake up one day and find you don’t have your own client base, you’re not in control of your own career, and, at worst, you’re expendable.’
Carmel points to his freedom to build as a key benefit of working at McDonald Hopkins: ‘The opportunities to build a book of business are really encouraging. I came here in 2018. I said, “I’m a restructuring attorney, and I’ve spent a lot of time in the litigation finance industry. We should create a litigation finance group.” And the firm fully supported me.’ He also notes that his firm established a private equity practice after he and several colleagues pitched management on the idea.
‘Client relationships run very deep, and it’s difficult to establish brand recognition if you’re just planting a flag of your own’ – Katriina McGuire, Thompson Coburn
More important to local and regional firms’ continued success, however, is their ability to compete on rates.
‘We’re positioned to take attorneys from larger firms that are sensing real rate pressure from clients and don’t have the flexibility to respond to that’, says McGuire.
‘Rates have increased across the board’, says Carmel. ‘But because we’re in the middle market we’re not putting them up by the same amounts as the larger firms are, so our value proposition has become better and better.’
In the words of one partner, ‘If you’re a client instructing a really large firm, you may be effectively paying to train younger attorneys. Especially on a mid-market transaction, you might see your matter passed down to less senior attorneys, and find yourself paying top-level rates for a team that isn’t exactly the A-team.’
Another partner argues that major incursions into the market create opportunities for local and regional firms to hire: ‘After a merger, a lot of lawyers find when the dust settles that they don’t want to remain as part of the bigger firm because their clients don’t want to pay their rates.’
Regional and national firms argue they are better placed to strike this balance than the larger international firms. ‘We offer our laterals a national platform, but in a way that the rate increases aren’t a turnoff to clients’, says McGuire.









