Winston & Strawn LLP - The Inside View

Laying down the gauntlet to the legal industry with a formidable litigation practice and “unique” niches, W&S hopes to stand for ‘worldwide and successful’.

Many years before Jennifer Hudson, this firm started out in windy Chicago with dreams of something bigger. Much bigger. Rather than rocketing to success on some kind of BigLaw American Idol (we couldn’t think of anything worse), Winston & Strawn has grown larger each year since its birth in 1853 and now sits firmly under its own global spotlight. Notorious for taking roles on high-flying, complex litigation, this firm also has a keen eye for pinching top-tier laterals and teams from competitors. In February 2021 the firm ballooned its Los Angeles headcount with 18 extra attorneys, most coming on board from local litigation boutique Scheper Kim & Harris.

In its home state of Illinois, Chambers USA ranks Winston in pretty much every practice area it operates in including antitrust, banking & finance, corporate, IP, litigation, and employee benefits & executive compensation. The firm’s other offices also score strong points – New York for antitrust, the California offices for energy, Charlotte for litigation and Dallas and Houston for disputes (especially white-collar investigations) and IP. Looking for some quirkier practices? Consider the firm’s nationwide rankings in shipping and maritime regulatory, sports, renewable energy, cartel antitrust law and e-discovery and information governance work.

“People aren't afraid to show their quirks and their genuine personalities.”

The zesty mix carries over to the types of people Winston attracts: “Everyone loves to joke around, and people aren't afraid to show their quirks and their genuine personalities.” Juniors told us it’s not just the youngsters bringing the humor, and partners play an instrumental role in this culture. “They are very accommodating and respect you and your personal life,” we heard. “We can have casual interactions as well as professional ones.”

In our 2021 research, Winston & Strawn hit the top 25 for Associate Satisfaction.>

Strategy & Future

In early 2020, Winston’s managing partner Thomas Fitzgerald told us W&S is keen to position itself as a national or global outfit, rather than a Chicago firm. Associates told us “that direction hasn’t changed at all throughout the COVID-19 pandemic.” After breaking the $1 billion revenue mark in 2019, it’s been “business as usual as much as possible and the firm’s done a good job of staying busy.” Lateral hires in DC and the launch of an energy and infrastructure group in Houston and New York point to continued success early in 2021…

“That direction hasn’t changed at all throughout the COVID-19 pandemic.”

The Work

Just over half of the juniors in our sample were in litigation, with about a quarter in corporate and the rest scattered around the firm’s specialist departments including real estate, employee benefits, energy, environmental and tax. Geographically, New York and Chicago housed over half of second and third-year associates between them. Winston has traditionally run a free-market assignment system from the get-go; revolution has since come, and first-years now enjoy a “system that regulates who gets staffed where based on availability.” Sources told us this helps eliminate “periods of feast and famine.” Everyone else remains in a free market, which some found problematic: “I’d prefer a more evenly distributed workflow so one person can’t end up jam-packed.”

For their first two years, litigation juniors act as generalists. “It ensures people get to try enough variety to make sure they naturally fall into the group best for them,” interviewees explained. Associates technically have to declare a specialty in their third year, “but you’re still open to work on whatever you want” even then. There’s plenty of choice – antitrust, IP, commercial litigation and white-collar defense are all here. Antitrust in New York covers a lot of sports work, navigating regulatory decisions about exclusionary conduct in the sporting world. Winston’s taste for lateral hires has added some extra spice to the practice: many of the IP team in Dallas originated at Fish & Richardson and brought in a lot of ‘soft’ IP work including trade secrets litigation. Juniors felt “they’ve kept a boutique feel in the work they do.”

“…an emphasis on really developing young attorneys and making them valuable members of the team.”

Disputes juniors can expect to work on research and discovery, as well as preparing expert reports and depositions and taking notes. On top of that are ample drafting opportunities including summary judgments, motions and oppositions. Normal circumstances would see juniors quickly building court experience, “but because of the pandemic we’ve mainly been doing court conferences over the phone.” Juniors told us the team places an “emphasis on really developing young attorneys and making them valuable members of the team.”

Litigation clients: Tate & Lyle, National Rifle Association, Panasonic. Represented pharmaceuticals business Hikma in over 700 national opioid litigations alleging negligence, fraud and violation of consumer protection laws among others.

Junior corporateassociates also act as “free agents” at first, “unless you specifically come into a specialty subgroup like real estate or tax.” Securities, M&A and finance are the three generalist groups. On the transactional front, Winston also handles work in the special purpose acquisition company space and private offerings that are not registered with the SEC. Annual reports and filings, FCC complaints, stock work and IPOs make up the securities practice; juniors were especially excited about new market offerings work. “You get to learn about interesting companies and your work has a direct impact on them,” one said. Private equity was the dominant trend in M&A for our sources – we heard that in New York this kind of work is “hard to get placed into. The group that does portfolio deals can be very insular and they like to work with the same people.” One junior joked: “They’re the jocks of the department.” In-demand areas can be competitive…

“Gold, airplanes, farmland… it’s a unique, esoteric practice.”

Cash flow financing, project finance and structured finance are subdivisions in the – you guessed it – finance practice. The firm’s project finance team deals with “financing of renewable energy, including lots of solar and wind farm projects.” Winston & Strawn is well known for structured finance work, representing borrowers and lenders in asset-backed financing. The assets involved can often be “non-conventional – gold, airplanes, farmland. It’s a unique, esoteric practice.” Juniors here typically work on checklists, compile merger pages and closing documents and sometimes get to draft filings and registration statements; some had opportunities to work directly with clients. Though certain junior roles are “not exactly substantive,” partners don’t create “any ceilings on allowing you to handle more challenging work if you’re excelling.”

Corporate clients: Groupon, Morningstar, TreeHouse Foods. Represented mobile games platform Skillz in its combination with special purpose acquisition firm Flying Eagle, valuing the company at $3.5 billion.

Career Development

Just like the Sufjan Stevens song, new associates head to Chicago for “very comprehensive training over several days.” This regime continues for six more months in their own (or during the pandemic, home) offices. “After that we have speakers come in to present and ad-hoc trainings throughout the year,” juniors told us. The firm assigns an associate and partner mentor to all, but many found that “all partners are supportive, always providing feedback and seeking juniors’ input.” Describing senior attorneys as “easy to talk to, laid back and approachable,” one W&S-er went on: “They care about my development as a junior attorney and actively reach out to me to gauge how I’m doing.”

“…gives you all the tools you need to be a success, wherever your career takes you.”

Sources told us Winston & Strawn “gives you all the tools you need to be a success, wherever your career takes you.” It’s no secret that not everybody will become a partner at the firm and “they’ve always told juniors that, even since summer.” That said, “there’s no revolving door,” associates suggesting that partnership is “still a realistic goal” for those who want to pursue it. For those who don’t, the firm provides a coaching and wellness team: “You can talk about your long-term goals. It’s all confidential and really helpful; not having to worry about repercussions does a lot for your wellbeing.” W&S alumni tend to go in-house, to government, charity organizations or startups while “maintaining positive relationships with the firm.”

Pro Bono

Winston’s attorneys can tackle “all kinds of pro bono – you can even bring your own matters in.” During interviews we learned of housing matters, helping fraud victims, preventing federal executions, defending victims of excessive police or prison guard force, work on charities’ contracts and researching human rights issues. LGBTQ-related pro bono was popular, such as helping refugees seeking asylum and helping LGBTQ ex-military upgrading their dishonorable discharges from ‘don’t ask, don’t tell.’ Associates suggested Winston “encourages everyone to do pro bono work. If you’re behind, they’ll reach out to give you opportunities.” Winston has a target of 35 hours per attorney (20 if you're a lateral in your first year at the firm), but many comfortably exceed that.

Pro bono hours

  • For all (US) attorneys: 80,424
  • Average per (US) attorney: 102

Hours & Compensation

Billable hours: 2,000 target

100 of that 2K can take the form of “accountable hours – pro bono, recruiting, articles and firm development work.” The remaining 1,900 should be client-billable work, but anyone’s who’s reached 2,000 hours “can do as much pro bono and accountable hours as they like.” Interviewees said the firm’s been “more flexible during COVID-19 because billables dropped a little.” In such situations, partners “reach out to help and push for you to overbill to make it up later.”

“…more flexible during COVID-19 because billables dropped a little.”

Most of our sources worked until 7pm on an average day, or the small hours of the morning and weekends during busy stretches. “When it’s not too intense I only work a few hours on the weekend,” one added. Although many hit the target and found it attainable, “not everyone made their hours last year. It’s not our fault, it’s the world’s, so management definitely understood.” In normal circumstances, not hitting the target does mean no bonus, but in 2020 those that didn’t meet their hours got a proportional ‘special’ bonus tiered at either the full amount or 50% or 75%. “I was pleasantly surprised that we still at least get something,” one said.


Let’s build a dating app profile for a typical W&S attorney. Our sources suggested their description would read: “Calm and laid-back, but very outgoing and easy to have conversations with about non-work topics.” We’d swipe right! Juniors in the Chicago HQdescribed their base as a “busy, connected hub” where attorneys are “all comfortable with one another and you don’t always have to maintain a professional persona.” Likewise in New York we heard that, despite the city’s reputation, “interactions are very casual. I feel no nervousness walking to a partner’s office or giving them a call.” Those in smaller offices told us “people are always talking in the hallway and going into each other’s offices. There’s a real community type of environment.”

“I’ll know COVID is over when I’m at Martini Friday!”

Insiders told us small offices (such as Dallas) are “very family-oriented. People aren’t going out and partying – you don’t have to sacrifice time with your family to be a good part of the group.” It’s in the larger bases that you’re more likely to find “the kind of people who want to work together and have fun together, not just turn up, work, then go home.” New York has traditionally hosted Martini Fridays, which pandemic-weary Winstonians “miss very much!” They represent an opportunity to “talk to partners you’re interested in more informally about their practice” as well as to “decompress with colleagues” over food and drink. “I’ll know COVID is over when I’m at Martini Friday!” Events have been scarce in lockdown, though Winston “tries to make efforts to keep everyone connected,” including a virtual holiday party. The firm sent out drinks and hired a magician to perform over Zoom, drawing mixed reviews – “exhausting” was one of the less kind descriptions.

Diversity & Inclusion

Many interviewees agreed that D&I is “definitely at the forefront of the firm’s model and mind.” Winston & Strawn is home to affinity groups that “provide mentors and allow people to foster more connections.” There is a diverse attorney retreat each year, which went virtual in 2020. There’s also a firm diversity committee, working to ensure “there’s no shortage of opportunities to get involved in events and hiring programs.” This caring bunch “reached out during lockdown, sending care packages and helping people stay connected.”

Winston & Strawn “sent out a firmwide email the day after George Floyd’s murder condemning that unequivocally and restating our commitment to diversity and inclusion.” Becoming more inclusive is a “slower process than some people would like,” but interviewees agreed the firm is “committed to a better future.”

Get Hired

The first stage: recruitment on and off campus 

OCI applicants interviewed: undisclosed

Interviewees outside OCI: undisclosed

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 chair of the hiring committee, explains. 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 tells 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, chair of the hiring committee. 


Applicants invited to second stage interview: undisclosed

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,” says O’Neil. 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 tells 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 chair of the hiring committee. 

Summer program 

Offers: 75 

Acceptances: undisclosed

Winston’s ten-week summer program provides “real work experience, including pro bono work, mentoring relationships, training, and networking opportunities,” O’Neil explains. 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,” notes O’Neil. 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, chair of the hiring committee.

Interview with Winston & Strawn's chairman Tom Fitzgerald

Chambers Associate: How did Winston handle 2020 and the tumultuousness that came with it?

Tom Fitzgerald: Like most members of the AmLaw100, we were very nervous. I don’t pull any punches when I tell you that. I was chair during the 2008 financial meltdown and that felt like an isolated issue, once liquidity was back in the system. While it hurt momentum, it didn’t extract a change in the business model. We recovered from that and in 2019 edged over a billion and 2020 just under a billion. But, because of our cost structure our profitability soared to the highest it ever had. The reason we’ve not maintained revenue is we should have had 12 trials in December. but we only had two. Those are now slated for this year so I think there will be a flow of revenue from those matters into this year 2021 and next year 2022. We believe the slight reduction in revenue is going to come back and we’re going to see it this year.

Profitability as I said was up to highest level ever. The reason for this was remove a cost factor for our law firm that has long term positive implications. All of our assistant work is now done in a resource center in Houston that also houses our Winston Legal Innovation Center. That work consists of correspondence, billing, document production, production of marketing materials and other materials. We’ve been able to centralize that, which allowed us to reimagine how we deploy our workforce. We made the decision to do that mid-year and give people very generous voluntary retirement packages. They were given six months of salary, which gave people time to relocate or retire.

We created efficiencies and professionalism in those functions, which to us was a worthwhile investment in the middle of a Covid year. We reached levels of profitability we’ve not yet to foresee. Elsewhere, the transactional area took a slight pause for about six weeks and came back – and we’ve never been busier there. Finance, private equity, restructuring.

So, we had a successful year – but we are not doing cartwheels over it because of the disaster of this pandemic. We’re thankful for the opportunity to continue to serve our clients and work but we do it with a heavier heart than we normally have. The loss of jobs and lives in the USA means we’re sad as well as thankful.

CA: Tell us a little about your partnership with Chinese law firm Yuanda

TF: We were given this opportunity by a friend of the firm and we thought that long-term it would be very important for us. The U.S. and China are the two biggest economies in the world, so we’ve got to work together. If we do, we both win! So, this strategic alliance is a long-term investment for the firm, and we’re excited to make it. Our firm thinks long term – as leaders, we’re stewards of the firm, and we want to be better each year. When you think like that, you think a little differently about long-term investment in your firm and personnel.

CA: What’s the thinking behind your newly formulated Tech Antitrust group?

TF: The first things is that those separate areas in our firm are both very strong practices. And antitrust includes not only tech but other practice areas as well such as banking, commercial and consumer. So that practice has several aspects to it. Similarly, our tech group has a lot of aspects to it that are important, and we’ve worked hard to develop and invest in those. I think what you’re seeing is that tech firms are becoming positioned in aspects of their practice and business in a way that means they’re butting up against antitrust laws. They’re using their market positions in ways that may not be copacetic with antitrust rules. This isn’t an area where antitrust has historically been important, but it’s becoming a bigger factor in the tech space.

The principles of antirust are similar in any area. They’re mainly horizontal issues affecting market share or cause to the consumer. They’re becoming very important in tech space and there’s some very interesting issues here. Those market definition questions haven’t been answered in tech like they have in other industries. There are a lot of legal issues to be resolved in that industry. And we can’t go in with any preconceived notions because it’s too early to tell and there haven’t been developments in the law.

CA: What’s the firm’s plan in navigating 2021 and beyond?

TF: You see it in the actions we’ve already taken. We have analyzed. My background is a business background - I’m a CPA. I was a tax lawyer and have always been fascinated with the business of the law. We took a look at some of the legal surveys and we concluded there were five markets where we need a substantial presence: New York, Chicago, Texas, California and DC. Why? Because people need and use a lot of legal talent in those areas.

We do not seek to be in every major city in the US. We seek to be substantial in those five markets, and then London and a practice in Asia. Once we tackle that, we can think about all the other areas of the world where people need legal services.

I believe that you can’t be well-known or have a big presence until you have the people. With 20 or 30 people, you can’t make an impact - we believe you need more people. Our investments will be tailored to that. With our joint venture with Yuanda, and with Scheper Kim & Harris in LA, we’re looking for opportunities to make that offering based on where there’s talent and where people need us. We feel very confident we’re going to get there in Texas, and while it may be harder in California, we’ll get there, we’ll succeed.




Winston & Strawn LLP

35 West Wacker Drive,
IL 60601-9703

  • Head Office: Chicago, IL 
  • Number of domestic offices: 9
  • Number of international offices: 6
  • Worldwide revenue: $981,200,000
  • Partners (US): 341
  • Associates (US): 400
  • Contacts  
  • Main recruitment contact: Lisa A McLafferty, Director of Attorney Recruiting & Development
  • Hiring partners: William C O’Neil, Chair, Hiring Committee
  • Diversity officer: Sylvia James, Chief Diversity & Inclusion
  • Recruitment Details 
  • Entry-level associates starting in 2021: 57
  • Clerking policy: Yes
  • Summers joining/anticipated 2021: 94 (1Ls: 19, 2Ls: 75)
  • Summers joining/anticipated 2021 split by office: CA 8, DC 6, IL 25, NY 32, NC 2,TX 21
  • Summer salary 2021
  • 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 and critical motion, capital markets, class actions, complex commercial litigation, consumer products, e-discovery and information governance, employee benefits and executive compensation, energy, project development, and finance, environmental law, financial services, financial services regulatory, health and life sciences, intellectual property, international arbitration, labor and employment relations, litigation, maritime and admiralty, mergers and acquisitions, special purpose acquisition companies, patent litigation, private equity, product liability, public finance, real estate, restructuring and insolvency, securities litigation, securitization, sports, tax, technology, digital media and entertainment, private client services, white-collar, regulatory defense and 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 15 offices in key financial centers across the world (Brussels, Charlotte, Chicago, Dallas, 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 2021:
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, 2021

Ranked Departments

    • Corporate/M&A: Private Equity: Highly Regarded (Band 1)
    • Energy: State Regulatory & Litigation (Band 1)
    • Labor & Employment (Band 4)
    • Litigation: White-Collar Crime & Government Investigations (Band 3)
    • Litigation: General Commercial: Highly Regarded (Band 2)
    • Litigation: White-Collar Crime & Government Investigations (Band 5)
    • Antitrust (Band 1)
    • Banking & Finance (Band 3)
    • Corporate/M&A & Private Equity (Band 2)
    • Employee Benefits & Executive Compensation (Band 1)
    • Environment (Band 3)
    • Intellectual Property (Band 2)
    • Labor & Employment: The Elite (Band 4)
    • Litigation: General Commercial (Band 2)
    • Litigation: Securities (Band 2)
    • Litigation: White-Collar Crime & Government Investigations (Band 2)
    • Tax (Band 3)
    • Antitrust (Band 3)
    • Litigation: Securities (Band 5)
    • Litigation: General Commercial (Band 4)
    • Corporate/M&A: Highly Regarded (Band 2)
    • Intellectual Property (Band 2)
    • Litigation: White-Collar Crime & Government Investigations (Band 1)
    • Real Estate (Band 3)
    • Litigation: General Commercial (Band 2)
    • Antitrust (Band 4)
    • Antitrust: Cartel (Band 3)
    • Capital Markets: Securitization: CLOs (Band 2)
    • Corporate Crime & Investigations: Highly Regarded (Band 1)
    • E-Discovery & Information Governance (Band 2)
    • Employee Benefits & Executive Compensation (Band 4)
    • Energy: Electricity (Regulatory & Litigation) (Band 5)
    • Energy: Oil & Gas (Transactional) (Band 4)
    • Intellectual Property (Band 4)
    • Private Equity: Fund Formation (Band 4)
    • Product Liability & Mass Torts: Highly Regarded (Band 2)
    • Projects: PPP (Band 3)
    • Projects: Renewables & Alternative Energy (Band 2)
    • Sports Law (Band 2)
    • Transportation: Shipping/Maritime: Regulatory (Band 1)