The Legal Cheek View
Hailing from the birthplace of Walt Disney, Michelle Obama, Harrison Ford and Michael Jordan, this Chicagoan native is putting up numbers around the globe, with its fresh appetite for internationalism and a particular strength in big-ticket litigation.
The brainchild of Harvard graduate Frederick Hampden Winston (who — fun fact — later became the American minister to Persia!), Winston & Strawn counts itself as a member of the elite ‘White-Shoes’ firms in the US. It has a strong presence in the States, home to ten of its fourteen worldwide offices. In recent years, however, this very American firm has set its sights on Europe — and London in particular.
When the firm’s global chair Stephen D’Amore took the Winston & Strawn reins in 2024, he described growth in London as “priority No.1”. D’Amore has proved to be a man of his word as partner headcount in London has been climbing steadily. In 2025, the London office picked up top lateral hires from its US-based cousins Skadden, Cooley and Dechert. And there is clearly more to come — “We need to be a stronger presence in London,” D’Amore declared.
Winston & Strawn also has international offices in Paris (D’Amore’s “priority No. 1A”), Brussels and São Paulo. The firm’s renewed focus on European expansion comes as it joins the ream of American firms shuttering operations in China. Having closed its Hong Kong base in 2024 (and leaving Beijing and Taipei in 2016) W&S announced in 2025 plans to shut down its Shanghai office, marking its exit from Asia. Clients in Hong Kong and Shanghai will continue to be serviced by the firm’s strategic alliance with local law firm Yuanda. There are currently no international or client secondments on offer but with the new focus on UK and European growth, we’re hearing rumours that jet-setting opportunities might be on the cards in the very near future.
Increased headcount, in combination with high demand and billing rate growth, has left Winston & Strawn a firm in fine fettle. Revenue increased by nearly 7% to $1.27 billion (£930 million) and its profitability is growing even faster: net income jumped 9.6% to $410.24 million (£300 million) and profit per equity partner (PEP) hit $3.5 million (£2.57 million). With strengths across litigation, specialised finance, private equity and M&A transactions, the firm performed well across the board. Work highlights from this past year include W&S’s representation of Suntory Global Spirits in a $1.2 billion sale of cognac brand Courvoisier to Campari.
The firm landed on British soil in 2003, opening a City of London base. In 2023 the London team moved into a swanky office space at 100 Bishopsgate where they roam the skyscraper’s 33rd floor, just above Magic Circle firm Freshfields. The office has recently undergone an expansion of an extra 5,000 square feet to cater for W&S’s swelling ranks. The refurbed space is designed to promote flexible and collaborative working and even operates on renewable electricity! “The office is pretty spectacular” said one new recruit, “everyone has a standing desk and there are sparkling water taps. The communal spaces are very nice and the office is generally very open and conducive to collaborative working.” Trainees are allowed to work from home on Fridays, and a standard WFH package including a monitor and keyboard is provided to accommodate for this.
The office plays host to around 25 solicitors, including 13 partners, as well as one or two carefully chosen rookies each year. As you might expect for such a small intake, the firm prizes itself on offering “real legal work” the minute you’re through the door and the trainees we spoke to echoed this sentiment: “Trainees are encouraged to work at associate level and take initiative and ownership of the work they are given, whilst also having an appropriate level of support,” explained one. “We are given real tasks that are key to the deal/case rather than just doing admin in the background.” Another praised the firm’s “lean teams” which “give trainees excellent opportunities to work on associate-level tasks.” What’s more, you’ll be taking on this “associate level” work for “a range of interesting clients”, according to our sources, with the London corporate team recently representing a significant investor in the multi-billion dollar acquisition of Chelsea Football Club owners, Fordstam Ltd. Other recent highlights include yet another multi-billion dollar, cross-border deal with Chart Industries on their acquisition of Howden and the firm also counts Motorola, Verizon, Tom Brady and the New York Stock Exchange as part of its clientele list.
Not that you’ll be talking quarterback plays and sharing stock tips all day, there are still the “traditional trainee tasks, such as preparing bundles, arranging printing or preparing signature packs” to be done at W&S. However, the recruits we spoke to were quick to note that “the admin heavy tasks are outweighed by the fact that most of the work is stimulating”. London services UK, US and international clients, with a fair amount of work done in emerging markets across Eastern Europe, Africa and the Middle East. The international arbitration and corporate teams are said to get some pretty exciting stuff, but trainees in the City can also enjoy seats in finance, restructuring and insolvency, commercial litigation and EU antitrust/competition.
On the topic of training, expect a stereotypically US approach to “learning on the job” with little to no “opportunities for formal training”. This isn’t necessarily a bad thing, in fact the rookies we spoke to felt it was a real positive to get “real work to do from the get go” with one adding that: “I feel like my training at Winston & Strawn has prepared me for qualification and managing matters as an associate.” Another eagled-eyed recruit has noted that “the firm has recently started to run more formal training for trainees and associates (internal and external as well as partner-led sessions)” and juniors are also invited to a European training seminar as well as the HQ in Chicago upon qualification.
One area where Winston does shed any American stereotypes is in its “very collegiate working environment” which is said to have no “competitive culture at all”. According to LC insiders, “everyone is happy to share knowledge / give support” and another trainee offered this insight into the working culture: “Winston is very junior heavy and as those juniors have started to become more senior, they have become great role models and support systems. I know that I can go to those people if I have questions about work, but also if it is feeling particularly hard that day and I need a pick me up. The office is very small so everyone knows everyone and what everyone is doing and if someone is struggling that is picked up on and everyone tries to help out however they can.”
This includes partners and higher ups who are noted as being “highly approachable for the most part”. Our spies reported of “regular catch ups with the managing partner (Nicholas Usher)”, a strong sense that trainee “feedback is taken onboard” and even feeling “comfortable asking superiors questions, even if they may be simple/seem silly” — imagine!
Despite its relatively small size the office manages to remain a social hub with “lots of social events including weekly drinks, office weekends away, ski trips, trainee/associate evenings, practice group nights out, Christmas and summer parties and holiday and qualification drinks etc.” (though we’re not sure what else ‘etc.’ could possibly include)! Our sources tell us that the firm puts a lot of effort into making these events happen and prizes its ability to get the troops rallied together, with some even hanging out on the weekends.
Other weekends might involve less ‘hanging out’ and more getting on with work alongside your fellow trainees in the office, as recruits report a mixed work/life balance at Winston & Strawn. Weekends and holidays “are generally respected” if not off-the-cards entirely, whilst “hours in the week are long.” One junior lawyer offered this reflection on their time as a trainee: “We work for an American law firm so of course we are not going to have the best work/life balance. As a trainee work/life balance was at times non-existent, working all hours and weekends and at times it did feel never ending and very hard.” That being said, the balance is said to improve massively at NQ level and rookies are healthily compensated for their efforts, with a recently boosted trainee salary starting at £56,000, rising to £61,000 in year two and £160,000 once qualified.
This stellar salary is complemented by a solid offering of perks. The lack of a canteen is supplemented by regular in-house catering with the firm recently bringing in a taco station to cook tacos for employees from scratch in the lounge. There’s also free fruit and snacks on offer, breakfast options every Monday and a bagel round on the last Thursday of every month. Not bad for a firm with no kitchen! Other, non-taco perks include the usual private healthcare and dental package as well as a personal concierge service for planning holidays (how fancy!). W&S lawyers also get £50 a month to spend on the wellbeing platform Heka – a particularly popular perk among our sources.
In legal tech news, the firm have recently launched their own Artificial Intelligence strategy group alongside ‘Winston Legal Solutions’ — a low-cost right-staffing model design to assist with some of the more routine, admin tasks trainees face day-to-day. For the meantime, however, our sources have previously complained that most of the benefits of this investment struggle to make it across the pond. Things seem to be looking up as though, as this year trainees report being “encouraged to use AI tools like Harvey and Copilot to streamline work processes” — plus, with so much movement in the States, you’d be mindful to watch this space.