Winston & Strawn LLP - The Inside View

W&S is one of Chicago’s most well-known BigLaw exports and offers its associates a generalist start in market-leading litigation and transactional practices. 

When you think of the great BigLaw firms that have emerged from Chicago, Winston & Strawn is definitely among the top entries on that list. Associates dubbed it “a litigation powerhouse” and that’s no exaggeration: about 60% of the juniors on our list were based in that department and Chambers USA bestows a lot of kudos on the firm’s general commercial, securities, and corporate crime and government investigations expertise in the litigious space. “Winston has extremely strong litigation practices and the experience you get as a junior associate is really hands-on,” a source observed. “I’ve worked on individual criminal defense cases right up to multibillion-dollar class actions!” 

But all this talk of litigation only tells one side of the story, because Winston is highly respected in the transactional space, too. Here, the firm’s private equity, projects, capital markets, and M&A work stands out, as an inspection of Chambers USA reveals. Sources here were chuffed to encounter “a mix of everything, from renewables-related M&A to infrastructure projects on both the developer and lender side.” Themajority of the associates on our list were located in the firm’s Chicago HQ and New York offices, with the rest split between the Charlotte, Dallas, Houston, LA, Silicon Valley, Miami, San Francisco and DC bases. 

The Work  

The firm was perceived to lean a little more on the free-market side when it came to work assignment, although centralized coordinators were in place as well. “When you first start, you will get assigned to matters,” a source noted, “but it’s safe to assume that this is a free-market system and you can do the work that you want to do.” The formalized system seemed to be more robust in the litigation department, with this interviewee explaining that “we report our capacity on a weekly basis and have an ongoing discussion with the assignment coordinator. But if you hit it off with a partner, they encourage the collaboration more! I wouldn’t want assignment to just be all of one or the other system, and that’s why I like this firm.” 

Litigation is pretty big time here!” a source beamed. The department is split into different subgroups – like complex commercial, white collar, antitrust, IP, and labor and employment – but juniors start as generalists and don’t have to pick a specialism until they’re three years in. Associates found that they got responsibility quickly: “There are opportunities to draft early on if you can show you can handle it,” said one, while another added that “within the first two years, I got to argue my first motion for a client and that was a big deal.” One interviewee noted that “it's pretty standard to expect document review as a junior, which is arguably the sexiest part of law!” When we questioned the appeal, they confirmed that it’s because “you aren’t just reviewing contracts, but also messages and emails, so it can be fun.”  

“I am constantly in contact with the government and clients, which is crazy!”  

The complex commercial cases tended to be on the larger size, while white-collar matters were reportedly staffed more leanly. This meant that our sources were able to “work closely with partners; draft outlines for depositions; participate in motion drafting; and research those motions.” And for those who want client contact? “I am constantly in contact with the government and clients, which is crazy!” Given the nature of the cases, the department comes with “high pressure and heavy workloads,” but one source told us: “I know I’m not alone, and I have confidence in everyone around me to be working at the same pace if not harder than I am!”  

Litigation clients: Fox News Network, Hertz Corporation, Philip Morris and Altria Client Services. Representing Hikma Pharmaceuticals during multi-district proceedings tied to opiate litigation. 

We were told that the corporate group has grown significantly in recent years and is split into areas like finance, M&A, capital markets and funds. Some found the “the corporate department to be quite M&A and private equity-centric,” whereas others found that “some of the partners are more finance-oriented, so I feel the work is more motivated in that way.” Despite certain trends emerging across offices, our sources were still able to dabble in all types of transactions thanks to their generalist status. When it came down to day-to-day tasks, juniors tended to register a quick rise in responsibility levels: “Within four to five months, I was doing deal checklists and leading calls, as well as completing first drafts and reviewing security documents.” On M&A deals, “there’s a decent amount of diligence to be done, so you’re acquiring and drafting ancillary documents as the deal progresses.” Those who had sampled finance work were very happy to tell us that they’d been able to “participate in the negotiations of credit agreements.”  

Corporate clients: The Jordan Company, SPX Flow, Arbor Investments Management. Advised MacLean Power Systems on its majority investment from Centerbridge Partners. 

Hours & Compensation  

Billable hours: 2,000 expectation for bonus eligibility

“We’re not a leader, but we do follow suit and raise whenever the market does!” 

We heard mixed opinions on Winston’s billable target. A litigator, for example, was “pretty happy with it, as I can still maintain a healthy balance and there are systems in place to support juniors,” while a corporate source said that “the number is sometimes hard to hit because of the market – I don’t think about it too much and just do the work!” Associates can count up to 100 hours of pro bono, DE&I, firm investment, and firm citizenship hours towards the target. If they reach it, they become eligible for a lockstep bonus, with amounts increasing in intervals for those who bill above and beyond. There were no complaints about the compensation at Winston: “We’re not a leader, but we do follow suit and raise whenever the market does!” 

Corporate juniors did find that they were “at the mercy of the deal pace – if things heat up, then the urgency and sporadic nature of the work increases and gets in the way of plans. I have spent some weekends working.” Another reflected that “it is BigLaw, so you’re expected to meet your hours, which means you can’t have an evening free sometimes. It’s sustainable right now, but I’m not sure how sustainable it would be if I had kids and rose up the ranks.” Our survey respondents recorded an average of 47.8 hours worked in the previous week, which was just below the market average we record. Areas with high hours included capital markets and litigation areas like securities, commercial, and patent. 

Pro Bono  

“...the team accommodated my interests by giving me local art projects to work on.” 

“The firm encourages you to get pro bono done as early as possible in the year to ensure that you actually do it,” an insider told us. To help them on their mission, Winston’s dedicated pro bono team ensures that attorneys receive emails detailing opportunities. The team also registers associates’ requests to get involved in a particular area: “I expressed a preference in the arts and the team accommodated my interests by giving me local art projects to work on,” a source confirmed.   

Another plus was that opportunities were said to be evenly tailored for both corporate and litigation attorneys. This meant that corporate associates had been able to help startups and non-profits with their transactional needs, while litigators had been looped into asylum matters and opportunities to file briefs in the supreme court. Others had drafted clemency petitions for prisoners; taken on wills and family matters; and got stuck into civil rights class actions. “If you have a side interest from law school – like criminal or public defense work – then you can do that here as part of your pro bono practice!” a source enthused. 

Pro bono hours  

  • For all (US) attorneys: 67,000
  • Average per (US) attorney: 66


“One of the dominant themes in the culture is that we try to be as collaborative as possible and build teams that are comfortable around each other,” a source remarked. Another told us that “the firm values people who work hard and work well with others, and you can really see that in the way we recruit: we don’t put as much value on the grades you got as we do on how hard-working and likeable you are! The best people in our practice are like that – they have grit and are selfless.” Our interviewees clearly liked their colleagues, as we heard about regular social events that brought people together, including martini Fridays, monthly trivia nights, holiday parties, and cocktail receptions.  

“...we go to fitness classes together!” 

With this array of activities in mind, sources concluded that Winston is a “place where people keep their doors open so you can come into the office and speak with them. They’ll pick up the phone to chat with you and ask you questions about a new dispute. It’s an open, forgiving place to work and we get together on a regular basis.” For this associate, that looked like “hanging out on the weekend with people from classes above and below me – we go to fitness classes together! There’s no big difference between lawyers and staff here, we all hang out.” Associates are encouraged to come into the office three times per week and social activities have been organized to entice people back.

Diversity, Equity & Inclusion  

A junior observed that “the classes around me are very diverse, but when you get to the more senior levels, the representation isn’t great.” These “issues are evident across the industry, and the firm is making an effort to address them by giving us billable DE&I hours and hosting events like a corporate Zoom session for women across the offices with panel speakers, which I appreciated.” Of course, “having affinity groups and meeting people outside of Zoom is great,” and one of the flagship initiatives that sources identified was Winston’sdiversity retreat, which takes place every other year and was most recently held in Miami.

“Our firm chair is making great waves on diversity – it is a priority.” 

Juniors were also positive about the sense of inclusivity at the firm: “As a person of color, you can feel like an outsider in a majority white environment, but I’ve never felt that here.” Another source in New York praised the racial diversity in the office’s corporate group but felt that “the rest of the office is less reflective of that, and litigation has more work to do.” Overall, our interviewees felt that the firm was “deffo aware of what needs to be done” and highlighted that “our firm chair is making great waves on diversity – it is a priority.” 97% of Winston’s survey respondents were positive about the firm’s efforts to recruit diverse associates, and efforts to fund diverse lawyers’ attendance at external events were also commended. 

Career Development  

Winston’s associates have access to a formal mentorship program that allows them to choose a senior associate and a partner mentor. This structure gives them the chance to select mentors who they click with enough “to hang out with them outside of work, which creates a comfortable atmosphere!” Sources also flagged that they could see a career development coach: “We talk about two to three times a year, and actually I should speak with them more often!” said one, while another found these conversations “helpful for giving me an open space to discuss what my concerns and priorities are.” 

“People do take you under their wing.” 

We were also told that there are plenty of opportunities to develop informal mentor relationships. “People do take you under their wing,” one insider noted, and their colleague added that they “use my informal mentors more. The diversity retreat was also important and allowed me to connect with lawyers of color and LGBTQ+ attorneys for guidance and support.” When it came to formal training, Winston University was a reliable provider of ongoing sessions: “It covers programs for attorneys at all levels, so as a junior you do some deposition training while as a mid-level you move on to trial and business development sessions.” This source added that “we have many Winston lifers here – we had a meeting with the partners, and we were told ‘If you want partnership, we will get you there!’ There are internal steps at the firm that help you to become a successful partner.” Of course, partnership isn't for everyone, and not all associates will head in this direction. 

Strategy & Future  

Associates felt that Winston’s a firm that gets ahead of the curve, as exemplified by the recent rush of firms to open in Miami, which the firm highlights as "a magnet for business and capital formation." Associates were delighted with the development. “That office has become a focus for growth," they noted, with one reckoning, "we’ll be looking to pursue more cross-border opportunities with Latin America.”

Another reflected: “When I started, Winston was seen as a litigation firm, but the corporate side has been growing, particularly when it comes to project finance and financial services work tied to digital assets.” This interviewee was reassured by the firm’s “financial health – we aren’t dependent on the technology sector, like some other firms – we do a little bit of everything!” Indeed, the firm tells us it anticipates growth across practices, highlighting private equity, finance, M&A, capital markets, antitrust, intellectual property, trials/CCL, and white collar in particular. In 2022, the firm took on 29 lateral partners, with roughly a 50/50 split between litigation and corporate.

Get Hired

The first stage: recruitment on and off campus

OCI applicants interviewed: 1,198

Interviewees outside OCI: 237

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 firmwide 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 judgment, 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: 287 (both 1L and 2L offers)

Acceptances: 100 (1Ls and 2Ls)

Winston’s ten-week summer program provides “real work experience, including pro bono work, mentoring relationships, training, and networking opportunities,” O’Neil explains. 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 Transactions. Litigation training is often focused on a mock trial and/or a deposition. The Transactions 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


Winston & Strawn LLP

35 West Wacker Drive,
IL 60601-9703

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 and infrastructure, project development, finance, funds, environmental law, financial services, financial services regulatory, health and life sciences, intellectual property and patent litigation, 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 16 offices in key financial centers across the world (Brussels, Charlotte, Chicago, Dallas, Hong Kong, Houston, London, Los Angeles, Miami, New York, Paris, São Paulo, 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 2022:
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, 2023

Ranked Departments

    • Intellectual Property: Patent Litigation (Band 5)
    • Labor & Employment: The Elite (Band 4)
    • Litigation: White-Collar Crime & Government Investigations (Band 3)
    • Private Equity: Buyouts (Band 5)
    • Employee Benefits & Executive Compensation (Band 5)
    • Litigation: General Commercial: Highly Regarded (Band 2)
    • Litigation: General Commercial: Highly Regarded (Band 3)
    • 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: White-Collar Crime & Government Investigations (Band 2)
    • Real Estate (Band 4)
    • Tax (Band 3)
    • Antitrust (Band 3)
    • Litigation: General Commercial: Highly Regarded (Band 5)
    • Litigation: Securities (Band 4)
    • Media & Entertainment: Litigation (Band 4)
    • Litigation: General Commercial (Band 4)
    • Corporate/M&A: The Elite (Band 5)
    • 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 2)
    • 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: Oil & Gas (Transactional) (Band 4)
    • Intellectual Property (Band 4)
    • International Arbitration: Highly Regarded (Band 2)
    • Offshore Energy (Band 2)
    • Private Equity: Fund Formation (Band 4)
    • Product Liability & Mass Torts: Highly Regarded (Band 2)
    • Projects: Power & Renewables: Transactional (Band 3)
    • Projects: PPP (Band 2)
    • Projects: Renewables & Alternative Energy (Band 2)
    • Sports Law (Band 2)
    • Transportation: Shipping/Maritime: Regulatory (Band 1)

More from Winston & Strawn: