Winston & Strawn LLP - The Inside View

All aboard a firm that places heavy emphasis on both powering ahead and letting off steam. Choo-choo-choose Winston.

CHICAGO in the 1850s was a buzzing hive of activity thanks to its central position in the national railroad system. The decade saw the city’s business boom and the population quadruple. (No, you're not reading the wrong guide, we're getting to a point.) While the city had a growing economy there was a distinct lack of law firms, so railroad enthusiast – and attorney – Frederick Hampden Winston saw an opening. In 1853 he set up shop in downtown Chicago and sowed the seeds for a law firm whose tracks now fan out way out beyond the Windy City to 16 offices in eight countries.

"Winston isn't afraid to show its face in the courtroom!"

Fast-forward 170 years and Winston’s still top-ranked nationally by Chambers USA for transportation work. But this is not really what the firm is all about today. Rather, its lawyers are known for being formidable litigators – "Winston isn't afraid to show its face in the courtroom!" is how one associate put it. The firm is Chambers-ranked in Illinois for general commercial and white-collar litigation – as well for for corporate M&A, banking, IP and other areas – and is recognized in four other states too, as well as nationwide for energy, projects, sports law, antitrust and IP.

The Work

At the time of our research more than half of juniors were in litigation and a quarter were in corporate, with the rest split between labor & employment, tax, real estate, energy, and employee benefits. A third each were based in Chicago and New York, with the rest hanging their hats in Dallas, Houston, Los Angeles, DC, and San Francisco.

Litigation juniors work as generalists for their first two years, meaning “you don’t get stuck in one area.” This is powered by a free-market work allocation system in which “you can really control what you do yourself. They've been great about letting me try a bunch of different things to find out what I like.” The free-market system was described as “stressful in the beginning,” but juniors were pleased that classes were “supportive of each other, so it doesn’t feel competitive.” Specialization comes after your third or fourth year when associates formally select a subgroup. “Pretty much everyone gets their top choice – but if there’s too many people applying for one group, they move you to your second choice.” However, even after specialization, associates are free to pick up work from other groups.

“He was Tom Brady’s lawyer!”

The type of work on offer ranges from general commercial/civil litigation to more specialist areas like white-collar, securities, and tax. We heard that there are a lot of breach of contract and public liability cases. Other notable groups include “a robust antitrust practice” and a “pretty big IP practice.” We also need to mention the sports law practice – “one of the heads of the firm [Jeffrey Kessler] is involved in a whole bunch of high-profile NFL cases. He was Tom Brady’s lawyer!” But what do litigation juniors get up to? “A lot of research,” said pretty much every single one of our interviewees – “I’ll often take a deep dive for several hours on a particular topic.” As well as that, there’s the opportunity to draft appellate briefs, complaints, motions to stay and dismiss and of course “more research.” Juniors told us that there’s “a lot of learning on the job – it can be daunting at first, but everyone’s nice and approachable if you need to ask questions.”

Litigation clients: Goldman Sachs, Dell, and Verizon. Represented Monsanto in a class action public liability case that claims a herbicide produced by the company is linked to cancer risk.

Corporate juniors also work as generalists for their first two years. Juniors can pick up work from subgroups such as securities, project finance, private equity, and M&A. The specialization process in corporate is “less formal” than in litigation –“you’ll likely already be working with your group anyway!” Juniors get their work through a free-market system that is supported by assignment partners who gauge workloads. They’re also the ones who dish out the types of work that associates want to try. Most juniors we spoke to tended to “find who you like working with so you can really build on that.”

Corporate clients: Citibank, Safeway Construction, and Credit Suisse. Represented the lender on a $3 billion construction financing for a new football stadium for the LA Rams.

In the M&A subgroup “middle-market private equity M&A deals have become our bread and butter. That practice is growing a lot, especially in LA and Chicago.” New York has a multidisciplinary Latin America team and LA has a renewable energy focus that “works on the debt side representing lenders – typically banks and financial institutions.” The projects practice acts for clients like this too, and we heard from one associate that it's recently been working on “a lot of stadium projects – you wouldn’t think it but there are so many stadiums being built right now!” Typical junior tasks include due diligence, writing memos, preparing signature pages, and keeping checklists up to date. More substantive work includes drafting escrow, LLC and credit extension agreements, with “direct client interaction on a daily basis.”


Winston & Strawn has a bit of a reputation for being a more conservative firm, and going back five or ten years the feedback we got from associates was in line with that. But now they're singing a different tune, with one saying: “It’s laid-back and there’s no face time culture, which is a big stress reliever.” Another interviewee told us about a cultural emphasis on supporting one another: “I’ve seen attorneys make sure someone has food delivered to their house if they’ve just come out of hospital and make sure their family is okay.”

“It’s a very social environment.”

Despite the Chicago office housing around 300 attorneys, juniors here told us it “doesn’t feel overwhelmingly big.” The office's social culture revolves around the “central cafe area everyone goes to for food and snacks.” Juniors really wanted to tell us that “it’s a very social environment. We’re not just keeping our heads down and then going home. I’ve been impressed by the emphasis on people bonding.” Elsewhere around the country others reported that their colleagues often “find ways to laugh and have fun.”

To help attorneys and staff let off steam, Chicago puts on a weekly happy hour and quarterly events. Juniors in New York go to baseball games and have devilishly debonair ‘Martini Fridays’ each week, DC interviewees reported going to spin classes and brunch, and LA juniors – in typical cool Cali style – told us that after work they “have wine and kick back. We go out for drinks, but we’re not fratty or anything!”

Diversity & Inclusion

Most associates agreed that “Winston is making a lot of big strides. In the past couple of years diversity has really come to the forefront of the firm’s goals.” Part of the initiative is a three-day diversity summit in Chicago – “minority attorneys come together and talk about how we can improve the firm.” Winston also invites diverse clients and in-house counsel to take part in seminars, meetings, dinners and other events like that. Interviewees rated it “a great way to get face to face with important people too!”

"I’m excited for what’s to come.”

A monthly speaker series has seen “some really interesting folks come visit recently.” Speakers include LGBTQ activist Sarah McBride and Wil Haygood, who wrote Showdown, the book about Thurgood Marshall. Winston has various diversity leadership initiatives: an LGBTQ group, a women’s group and WALI (the Winston Asian Leadership Initiative) which put on events such as film screenings and trainings. 

Another initiative that gained praise is the “very generous” family leave policy, which consists of 20 weeks paid leave and four weeks unpaid. The policy is also gender neutral – “so all parents can take advantage of it.” Tied to this, we heard attorneys can and do make partner while working part-time. We heard there has also been “a wellness push this year to reduce mental health stigma and provide tools and coping mechanisms.” Associates were generally very impressed with the firm’s efforts, and were aware that “it’s one step in a series of many! I’m excited for what’s to come.”

Career Development

Associates start off by attending a seminar-based training program called Winston University – “it’s like school inside the firm!” Training is then offered throughout the year – “on a regular basis there are presentations on topics like ‘how to be successful at Winston’ at which older associates go through things with us and answer questions.”

Career progression at Winston is all about “the overall, long-term outlook and creating your own path.” There’s a focus on talking about your future early on, and “a new talent development team are starting to provide transparency about identifying if you’re on track to be partner.” As part of this, a career coach provides an “open and confidential way to get career advice on your future, whether it’s inside or outside Winston's walls.”

Annual reviews were also praised for being “very helpful – the firm’s very transparent about what’s expected each year, but they do take a holistic approach on how you’re developing overall.” A mentor-mentee program gives each pairing a budget to “go to lunch or the driving range – you can use it for anything.”

Pro Bono

It’s been inspiring to see the firm's and partners’ commitment to pro bono projects,” one junior said. Associates are encouraged to bill at least 20 hours of pro bono each year, and aim for an overall goal of 35 hours: “It’s very easy to get toward that – there’s ample opportunity!” We even heard of juniors doing anything up to 350 hours. 100 hours count toward the initial 2,000-hour billable target. Once you’ve hit that, every pro bono hour counts toward the higher bonus tiers.

"A dedicated staff of pro bono counsel.”

Pro bono opportunities on offer include asylum cases, life planning for vulnerable people, veterans affairs, adoption issues, helping nonprofits with corporate matters, and advice clinics for immigrants and the LGBTQ community. Associates get their pro bono work through “a dedicated staff of pro bono counsel – they’re all very engaged and will talk to you individually about what kind of pro bono you want to be doing.”

Pro bono hours

  • For all attorneys: 76,103
  • Average per attorney: 84

Hours & Compensation

Attorneys have a billing target of 2,000 hours, 1,900 of which must be client billables – the other 100 can be pro bono and/or include 50 hours of firm citizenship and investment work. All our interviewees had indeed hit their 2,000-hour goal in 2018, with some getting closer to 2,500 hours (often thanks to a hefty amount of pro bono work). Interviewees rated the goal “very reasonable – it’d be hard to not hit your hours! It’s so busy.”

We heard that a junior's typical daily hours are 9am to 7pm and that's it's common to work a couple of hours from home in the evenings after that. If you're coming up to a trial or a closing, those numbers rocket higher. “In order to succeed at Winston you have to be willing to work extremely hard,” one steely source said. But partners’ attitude helps ease the pain – “one deal was so awful that the day after it closed the partner said to take several days off and put our out of office on.”

Another way juniors keep their stress levels down is by taking advantage of the “pretty liberal working from home policy.” That said, the flexibility to do so “does depend on who you’re working with. The more traditional partners are in the office five days a week no matter what!”

Though most interviewees were happy with their compensation, some felt that the additional bonuses you can get for billing more beyond the 2,000-hour goal “may not be worth the trade-off. I’d prefer to hit 2,000 and be left alone!”

Strategy & Future

The firm is definitely growing and it’s great to be a part of that!” one junior said, excited about the track the firm is on. Commenting on the firm's recent hikes in revenue, managing partner Thomas Fitzgerald tells us: "Now the government is up and running – and fingers crossed will stay up! – we will hopefully see a billion this time." Winston is getting very close to that billion-dollar revenue mark: in 2018 the firm pulled in $991 million.

Get Hired

The first stage: recruitment on and off campus

OCI applicants interviewed: 1,404

Interviewees outside OCI: 38

Winston generally focuses on OCIs from the country’s top law schools. The firm also attends job fairs that “allow us to focus on recruiting diverse candidates and those with technical backgrounds interested in specific areas of the law,” Bill O’Neil and Suzanne Jaffe Bloom, co-chairs of the hiring committee, explain. Winston generally interviews 1,300 students firm-wide each year. Interviews are typically conducted by a team of two attorneys – often a partner and an associate from different departments.

“Our interview questions tend to focus on three core values: intellect, leadership and interpersonal skills, and grit,” O’Neil and Jaffe Bloom tell us. For intellect, interviewers ask questions that are aimed at revealing students’ analytical skills, judgment, and decision-making process: “We may ask how their undergraduate major will prepare them to tackle some of the challenges they’ll face as a lawyer.” For leadership, interviewers focus on students’ interests outside of the classroom and their interaction with others: “We may ask about experiences they’ve had working on teams and the roles they play; challenges they’ve faced as they’ve adapted to law school; their proudest accomplishment, and what sort of activities they engage in for fun.” Finally, for ‘grit’, they’re on the look-out for work ethic, motivations, business savvy-ness, and resilience: “We may ask about a student’s most challenging work or school assignment and how they handled it; steps they’ve taken to ensure success in law school; the career path they would have chosen had they not gone to law school; and their most rewarding work experience.”

Top tips for this stage:

“Be yourself.  But be the best version of yourself.  Listen carefully to the questions and try to answer using examples from your own experiences. Genuine answers are the best answers.” – Bill O’Neil and Suzanne Jaffe Bloom, co-chairs of the hiring committee.



Applicants invited to second stage interview: 592

In general, each student meets with at least four attorneys – a combination of partners and associates. Each interview typically runs between 20 and 30 minutes. Interviews are held in the attorneys’ offices, which “provides opportunities for students to see our space and informally meet others at the firm as they are escorted from office to office,” say O’Neil and Jaffe Bloom. A callback interview could also include a lunch, coffee break or another meeting in a less formal setting.  Winston also hosts evening interview programs in some offices.

“At the callback stage, we are primarily focused on “fit”—both for us and for the student,” O’Neil and Jaffe Bloom tell us. “At this stage, we are examining our mutual chemistry and cultural fit. We ask questions that are designed to allow the candidates to demonstrate in greater depth their interpersonal and leadership skills, their grit, their analytical skills and judgement, and also what drives them.”

Top tips for this stage:

“Listen carefully; be genuine; share your unique experiences and perspectives; and show us that you know about our firm.  But be prepared to do that for a longer period of time over the course of back-to-back interviews.  Remain enthusiastic and engaged throughout each of the interviews.” Bill O’Neil and Suzanne Jaffe Bloom, co-chairs of the hiring committee


Summer program

Offers: 218

Acceptances: 63

Winston’s ten-week summer program provides “real work experience, including pro bono work, mentoring relationships, training, and networking opportunities,” O’Neil and Jaffe Bloom explain.The firm has an open summer program, which means that summer associates are not assigned to a department or practice group: “We find that our summer associates appreciate having flexibility during their summer program to work with multiple practice groups to determine which group best fits their interests.” Assignment coordinators assist summers in getting assignments based on summers’ preferences.

Summer associates are assigned at least one formal mentor and there is a formal lunch program that allows any attorney to take one or more summer associates to lunch: “This is a great opportunity for summer associates to connect with attorneys in a less formal environment,” note O’Neil and Jaffe Bloom. The summer program focuses on providing training opportunities for all summer associates across Winston’s two major departments: litigation and transactional.  Litigation training is often focused on a mock trial and/or a deposition. The corporate component typically consists of a workshop designed around the negotiation of a purchase agreement.

“Social activities are crucial components of our summer program and provide summer associates with a great feel for the firm’s culture.” The firm has many social events that “allow our summer associates to share fun experiences and develop strong personal relationships with each other and with our attorneys.” Some of these events include sporting, art and cultural excursions, as well as lunches and dinners.

Top tips for this stage:

“One of the greatest benefits of our summer program is the opportunity to build deep, meaningful, and lasting relationships with peers and mentors.  When our summer associates return as full-time associates 16 months later, it is those relationships that allow them to hit the ground running and access great professional development opportunities early in their career.” Bill O’Neil and Suzanne Jaffe Bloom, co-chairs of the hiring committee.

Winston & Strawn LLP

35 West Wacker Drive,
IL 60601-9703

  • Head Office: Chicago, IL 
  • Number of domestic offices: 9
  • Number of international offices: 7
  • Worldwide revenue: $991,036,557
  • Partners (US): 382
  • Associates (US): 407
  • Contacts  
  • Main recruitment contact: Lisa A McLafferty, Director of Attorney Recruiting & Development
  • Hiring partners: Suzanne Jaffe Bloom, William C O’Neil, Co-Chairs, Hiring Committee
  • Diversity officer: Sylvia James, Director of Diversity & Inclusion
  • Recruitment Details 
  • Entry-level associates starting in 2019: 64
  • Clerking policy: Yes
  • Summers joining/anticipated 2019: 79(1Ls: 16, 2Ls: 63)
  • Summers joining/anticipated 2018 split by office: Charlotte 2, Chicago 23, Dallas 13, Houston 4, Los Angeles 6, New York 21, San Francisco 5, Washington DC 5
  • Summer salary 2018
  • 1Ls: $3,653/week
  • 2Ls: $3,653/week
  • Split summers offered? No
  • Can summers spend time in an overseas office? No

Main areas of work

Antitrust/Competition, Appellate & Critical Motion, Capital Markets, Class Actions, Complex Commercial Litigation, Consumer Products, eDiscovery & Information Governance, Employee Benefits & Executive Compensation, Energy, Project Development, & Finance, Environmental Law, Financial Services, Financial Services Regulatory, Health & Life Sciences, Intellectual Property, International Arbitration, Labor & Employment Relations, Litigation, Maritime and Admiralty, Mergers and Acquisitions, Patent Litigation, Private Equity, Product Liability, Public Finance, Real Estate, Restructuring & Insolvency, Securities Litigation, Securitization, Sports, Tax, Technology, Digital Media & Entertainment, Private Client Services, White-Collar, Regulatory Defense & Investigations

Firm profile

 For more than 165 years, Winston & Strawn LLP has served as a trusted adviser and advocate for clients across virtually every industry. In that time, through careful growth and thoughtful fiscal management, we have built a law practice with tremendous breadth and a global reach. We are proud of the many accolades we have received over the years—a tribute to our lawyers’ creativity, flexibility, depth of experience, and commitment. The most meaningful accolade to us, though, is the continued trust and confidence of our clients.

With nearly 1,000 lawyers and 16 offices in key financial centers across the world (Brussels, Charlotte, Chicago, Dallas, Dubai, Hong Kong, Houston, London, Los Angeles, Moscow, New York, Paris, San Francisco, Shanghai, Silicon Valley, and Washington, D.C.), we bring an understanding of the global legal issues our clients face to both transactional and dispute-related matters.


Law Schools attending for OCIs in 2019:
Please visit the Careers section of for a list of OCI Schools.

Summer associate profile:
Winston & Strawn prefers strong academic performance, participation in law review or other law school publications or competitive endeavors and a good balance of academic and interpersonal skills.

Summer program components:
Summer associates have the opportunity to learn about a wide range of Winston practice areas and the specialized skills each one demands. Individual department presentations allow summer associates to meet lawyers from specific practice groups who detail what they do in their daily practice. The firm’s ‘Highlights Lecture’ series gives an inside look at some of the most publicized and interesting cases that the firm handled in the past year. In addition, the firm offers a practical training component that provides hands-on experience with activities such as drafting a legal research memorandum, negotiating a deal, drafting an IPO document, taking a deposition and trying a case in a mock trial. Summer associates learn from veteran Winston attorneys with years of experience and insight, who make the law come alive through examples, personal experience and anecdotes. In addition, summer associates have the opportunity to build relationships with attorneys through a variety of social activities throughout the summer.

Social Media

Linkedin: winston-&-strawn-llp
Twitter: @winstonlaw
Facebook: WinstonStrawnLLP
Instagram: winstonstrawnllp

This Firm's Rankings in
USA Guide, 2019

Ranked Departments

    • Bankruptcy/Restructuring (Band 3)
    • Energy: State Regulatory & Litigation (Band 1)
    • Labor & Employment (Band 4)
    • Antitrust (Band 3)
    • Banking & Finance (Band 3)
    • Corporate/M&A & Private Equity (Band 2)
    • Environment Recognised Practitioner
    • Intellectual Property (Band 2)
    • Labor & Employment (Band 3)
    • Labor & Employment: Employee Benefits & Compensation (Band 1)
    • Litigation: General Commercial (Band 2)
    • Litigation: White-Collar Crime & Government Investigations (Band 2)
    • Tax (Band 3)
    • Antitrust (Band 3)
    • Litigation: General Commercial (Band 4)
    • Intellectual Property (Band 2)
    • Litigation: General Commercial (Band 4)
    • Litigation: White-Collar Crime & Government Investigations (Band 1)
    • Real Estate Recognised Practitioner
    • Antitrust (Band 4)
    • Antitrust: Cartel (Band 3)
    • Capital Markets: Securitisation Recognised Practitioner
    • Corporate/M&A: Highly Regarded Recognised Practitioner
    • Energy: Electricity (Regulatory & Litigation) (Band 5)
    • Intellectual Property (Band 4)
    • Projects: Renewables & Alternative Energy (Band 2)
    • Sports Law (Band 2)
    • Transportation: Shipping/Maritime: Finance Recognised Practitioner
    • Transportation: Shipping/Maritime: Regulatory (Band 1)