Winston & Strawn LLP - The Inside View

One of Chicago's finest, this golden oldie is jazzing up its traditionally conservative image...

1853 was the year we could, for the first time, eat potato chips, protect our homes with a burglar alarm, enroll at the newly created University of Florida, and welcome the 14th President of the US, Franklin Pierce (usually ranked among the worst). That year long ago in the mists of time also saw the birth of Chicagoan stalwart Winston & Strawn. Despite the firm's impressive longevity, however, it isn't stuck in its ways. While Winston may once have had a reputation for being traditional, the associates we spoke had found this was changing: “It's still conservative in some ways because it's a law firm, but even the most prominent partners are very nice and approachable,” one junior told us. “As a result, the rest of the culture is pretty open.”

And the culture isn't the only thing that's evolving; this conqueror of the courtroom continues to expand in litigation and other practices for which it's less well known. Winston's managing partner Tom Fitzgerald tells us that "we're currently developing our corporate practice, with laterals this year from Pillsbury and McDermott, and we will continue to follow that strategy." As well as general commercial litigation, top-ranked practices in Chambers USA include intellectual property, transactional media & entertainment, energy, and shipping regulation. Winston's corporate/M&A and private equity expertise in Illinois is also highly regarded.

The Work

Around 60% of new associates go into litigation, while corporate accounts for roughly a quarter of juniors. The rest go into smaller groups including energy, employee benefits, labor & employment, real estate, and tax. Work assignment for most is based on a free-market system, which associates appreciated: “I was able to come in and align myself with partners who did the sort of work I wanted.” The system for New York newbies is more mixed: associates can talk to someone if they want more work or feel swamped, “but it's not formalized – we're not obliged to get work through the assigning partner.”

“I was able to come in and align myself with partners who did the sort of work I wanted.”

The litigation department offers associates a broad-ranging practice, which includes commercial disputes, patent litigation, white-collar crime, antitrust and bank fraud. “I like the fact that for associates who don't want to specialize, you can diversify,” one junior found. “It's good to get experience in different areas – it can be monotonous otherwise.” For the younger associates, the day-to-day involves “a fair amount of doc review and other tasks that are at the bottom of the totem pole,” although more substantial duties include second-chairing a deposition and drafting initial motions. As you begin to climb the proverbial totem pole, responsibility levels increase. “I've already taken depositions, argued motions in federal court, and had extensive briefing experience,” one third-year told us proudly, adding that “over the past eight months I've had more and more direct contact with the clients.” Among the clients that associates described were Fortune 100 companies, IP firms and technology companies.

When it comes to the fast-growing corporate group, we spoke to some newbies who had already begun to taper their practice. One junior explained the benefits of this: “If you specialize earlier, you do the same types of tasks over again, and the partners start to trust you more. As a result I've been able to get more responsibility.” Others, meanwhile, were still in the more generalist stage. “I've done some M&A, securities and lending – we have the ability to try everything until we decide what we like best.” We heard that private equity M&A was a particularly busy group, with deals ranging from “north of $3 billion to as low as $1 million. I'd say Winston's sweet spot for private equity is generally below $500 million.” This translates into some fairly substantial tasks for the juniors: “I've been able to take the first crack at drafting stock purchase or asset purchase agreements, and I've had some responsibility with negotiating ancillary issues.” One newbie added that “I've also become the primary client contact on some deals.”

Pro bono & Hours

For those who felt they hadn't yet had a chance to sink their teeth into meatier tasks, pro bono is a good way in. With four full-time pro bono attorneys, opportunities are abundant. On one domestic violence case, “it's been great because the partner let the associates take the lead. The first depositions I took were for a pro bono case.” Another added: “I've done two Seventh Circuit appeals, and I got to do all the briefing and the arguments myself.” Other examples we heard were immigration and adoption cases, and working on an assignment for the Hurricane Sandy Relief Fund. One source told us: “I've done a few patent applications for small entities that normally wouldn't be able to afford our rates, such as those doing work in the Third World.”

"The first depositions I took were for a pro bono case.”

Attorneys can count 100 pro bono hours toward their 2,000 hour billing target (increased from 50 a few years ago). Associates who hit this number receive the base bonus. After 2,200 they move to a higher tier bonus which increases in 100-hour increments, “so I got rewarded for the extra work I did.” An added incentive to do more pro bono is that if associates hit their billables, they can count any extra pro bono hours towards a higher bonus. “Once you hit 1,900 hours in regular billables, the firm will count however many pro bono hours on top of that,” one newbie explained. “I had a friend who billed 400 pro bono hours, but because he hit 1,900 hours he could count them all toward his bonus – it's nice padding.” In June 2016, the firm announced salary rises for associates in all its US offices, not just New York.

"I got rewarded for the extra work I did.”

The sense was that associates are “generally expected” to reach the 2,000 hour mark, with most of our interviewees having no problem at all in reaching it. Those in corporate in particular cited a very busy year, and many had far exceeded the target. That said, there aren't huge repercussions for any who don't reach 2,000: “I have friends that weren't able to hit it and they were fine – they just didn't get the bonus.” There's no formal vacation policy at Winston, which meant younger juniors sometimes felt uncomfortable taking time off: “I didn’t take vacation during my first year because I felt like it wasn’t appropriate.” Generally, though, our interviewees reported taking around two weeks off.

Pro Bono Hours 

  • For all attorneys across all US offices: 50,767 
  • Average per US attorney: 64

Training & Development

First-years at Winston are introduced to the firm with a week of orientation in Chicago, followed by weekly, hour-long sessions on various topics. For litigators, topics include how to prepare for trial, steps for discovery, and how to perform doc review, and every two years newbies gather in the Chicago office for firmwide deposition training. For those in corporate, training is on “anything from an overview of a private equity deal to secured lending and SEC filings.” Juniors in this department also spoke of doing sessions outside the firm: “PLI [Practising Law Institute] has seminars throughout the year which we can go to for free. I recently did one on drafting M&A contracts.”

“You have to go and ask for feedback.”

When it comes to feedback, the firm has a yearly evaluation which was described as “very brief,” and in the interim “you have to go and ask for feedback.” Interviewees weren't bothered by this, however, particularly as “everyone's willing to have that conversation with you.”

Culture & Offices

Some associates spoke of Winston's reputation for being fairly formal and conservative. Those in DC felt that “it's definitely hierarchical.  For instance, there's some extra capacity in the office, so technically everybody could have window offices, but in spite of this, first-years are required to have interior offices with no windows. Every year you move offices to a better view!” Other DC juniors agreed, pointing to the smarter smart dress code, although “there are people who also wear business casual, and our office has started doing jeans Fridays.”

"I've never once felt too timid to be able to ask questions.”

Associates in the Chicago HQ reported a shift in the culture over the past few years. “Previously, the firm had a reputation for being a bit formal, but I can tell you that in the past year alone it has changed dramatically,” one newbie assured us. Another elaborated: “I feel very comfortable with the people I work with. There's always an added layer of formality when you're working for a partner for the first time, but I've never once felt too timid to be able to ask questions.” And although many described Chicago as a family-friendly office, socializing isn't off the cards: “We have happy hours every Friday, then within our group we do events every month, whether that's a training event or a completely informal cocktail hour at a bar or restaurant.” Interviewees also pointed out that the removal of 'Ms.', 'Mrs.' and 'Mr.' from office name plates, as well as the opening of a new café for all staff (and not just associates), had gone a fair way to expelling any formality that might have lingered. We're sure it also doesn't hurt that the office space itself is “amazing,” and associates all have their own exterior offices: “Mine overlooks Lake Michigan, which is beautiful.”

“It's not stuffy at all!”

The Big Applers disagreed the most about Winston's traditional image. “It's not stuffy at all!” We were assured. “It's a big firm so obviously we have all different kinds of people, but everyone hangs out and we have a lot of social events.” Another interviewee expanded: “Every Friday we have a themed, officewide happy hour. We've had one for Mardi Gras and the Superbowl, and the firm puts on a food spread and an open bar. It's a nice time to relax and a great way to talk to partners and get new work.” The New York office, located in the MetLife Building above Grand Central, was praised for it's “well-kept” appearance, which is “all marble and very polished.” Another source added: “We're on the 42nd floor, so the views are pretty stunning.” Apparently, the cast and crew of The Good Wife even did some filming here. Juniors in New York share an office for their first two years.


“They're trying to make sure women are being promoted and that minorities are hired, but if you look at the make-up of the firm, right now it's not very diverse,” one junior acknowledged. That said, the firm is “definitely trying to fix that,” in part through its very active women's initiative. “We have a book club and dinners, and when new female partners were promoted they did a celebratory dinner and drinks for the female associates.” Someone else added: “We did a wine and cheese pairing event for all the female attorneys in the Chicago office.” The firm also has a parental leave liaison, who “helps to make it a more smooth transition” for those leaving and returning from maternity or paternity leave.

Winston has a diversity committee and affinity groups for ethnic minorities and LGBT attorneys, and offers three scholarships to diverse summers every year, helping them pay for their third year of law school. While the firm is making efforts, “it's still very Caucasian white male,” particularly at partner level.

Get Hired

"It's not intelligence but attitude that differentiates a candidate."

Bill O'Neil, co-chair of Winston's hiring committee, informs us that intellect, grit and interpersonal skills are the three key traits he looks for in a candidate. He continues that "public sector experience is a plus. For example, an internship at the SEC or DOJ is attractive on a resume." Associates echoed O'Neil's third point: that “the firm wants someone who's personable,” and this needs to shine through at interview. As one associate who had been involved in the recruiting process informed us, “I assume most of the people we're speaking to are intelligent. We're not doing rocket science, we're doing legal paperwork, so to me it's not intelligence but attitude that differentiates a candidate.” After all, "you don't want to be working on something until 2am with someone who is totally deadpan.” And an affable character is also useful because many at Winston “have to be able to interact and respond to clients on a daily basis.”

Strategy & Future

We were told that in the past, associates felt that they weren't being kept in the loop at Winston, “so now they're trying to get us more involved at different levels of the firm, and they're making the effort to tell us what's going on.” One newbie added that “they had a meeting just over a year ago to explain some of the new policies related to pro bono, and about being more transparent with the path to partnership.” All attorneys now also receive a copy of the firm's finances. “I think they've started to open up because of people telling them they’re a bit closed.”

"They've started to open up .”

The work has also seen a strategic shift in the past few years: “Several years ago, Tom Fitzgerald made it a point to grow the corporate group, so by the time I came into the firm, it was already much larger than in the past, and it's continued to be one of the fastest-growing parts of the firm.” 

Chambers interview with managing partner Tom Fitzgerald

Chambers Associate: How's 2015 been for Winston & Strawn?

Tom Fitzgerald: We've had a record year in terms of revenue and profitability, which is the direct result of the hard work of our attorneys and our staff. It's also a measure of our dedication to delivering exemplary client service.

We scored a number of victories in landmark litigation matters and guided our clients through several of the year’s highest-profile corporate transactions. We handled Tom Brady’s case against the NFL in the “Deflategate” matter, which garnered widespread media attention. We also amassed a number of precedent-setting victories for our clients in federal and state courts across the country, including a U.S. Supreme Court win in one of the most important and long-awaited securities litigation matters in recent years. In addition, we represented a few of our corporate clients in transactions that exceeded $1 billion.

CA: What do you think the firm will look like in the next three or four years?

TF: I think that is a difficult question to answer in today's legal environment. Firms need to focus on continually developing their practices to address emerging legal and regulatory threats and to seize opportunities to assist our clients with a growing number of corporate transactions. We are focused on acquiring the best talent out of law school to meet these challenges. We are deeply invested in our summer associate program, and we’re committed to training our attorneys throughout their careers. We’ve also made significant investments in training programs to equip associates with the skills necessary to become partners.

We’re currently focused on developing our corporate practice, and we’ve added significant lateral talent this year from Pillsbury and McDermott. We will continue to follow that strategy going forward. At the same time, we think our strong litigation brand will give us opportunities to develop that practice as well. We couple these priorities with a very successful lateral integration program, and that has served us well in expanding the range of services we provide to our clients.

CA: Are there any plans to open new offices?

TF: Not at this time. Geographical expansion is always driven by client need and opportunity, and that takes careful thought and deliberation. Right now we're looking to bolster our capabilities in the offices that we currently have.

CA: What is the firm doing to promote and encourage diversity?

TF: First and foremost, we've made dramatic changes to our leadership structure to boost representation of women and minority partners. We now have five women on our executive committee (up from two), and we appointed a woman partner to lead our Chicago office – which is our oldest and largest office. Our San Francisco office is also led by a woman. In addition, a diverse partner runs our tax practice, and several women chair firmwide practice groups. And we are continuing to look for opportunities to further our commitment to diversity in all areas of the firm.

CA: The associates we spoke to felt that Winston's culture is evolving from its traditionally conservative values. Would you agree?

TF: Our culture has been and remains grounded in fiscal conservatism. This means not incurring debt, avoiding recourse liability at the partnership level, and being very sensitive to how we manage the firm. But at the same time, our culture is based upon mutual respect: the partners and associates here really respect each other and our professional staff. Secondly, our partners recognize that in order to succeed, the firm has to continue to evolve, to become more efficient and forward looking. So while we are fiscally conservative, we also understand the need to adapt to changing marketing conditions and evolving client needs to remain relevant and help our clients with a broad range of legal needs.

CA: What would you say to our student readers that may be interested in applying to the firm?

TF: I think there are three things that young lawyers want. First, they want to be paid fairly, and we certainly believe that our compensation structure satisfies that requirement. Second, this generation is more experienced and skilled than previous generations, and training and development are especially important to them. Finally, young lawyers want opportunity; they want to know that if they do good work and develop their skills, they have the possibility for advancement. We offer all of those things.

CA: What do you think makes Winston stand out from other law firms?

TF: Winston enjoys a position among the best firms in the U.S. and around the world because of our exceptional client base and the depth of our talent at every level of the firm. It is also due to our commitment to training young lawyers and giving them opportunities for professional growth. This past September, we made added a number of partners under the age of 45 to our leadership team. That change demonstrated the firm's commitment to develop and promote the next generation of leaders at Winston.

Chambers Interview with Bill O'Neil, co-chair of the hiring committee

Chambers Associate: How do you pre-screen candidates? What are the key things you look for on a resume?

Bill O'Neil: My partner [Suzanne Jaffe Bloom] and I took over the Hiring Committee in June 2015. We have attempted to bring some new energy and perspective to the hiring process at Winston. We've tried to really communicate to our lawyers across the firm a clear set of objectives in terms of what we're looking for in a Winston attorney. We completely revamped our evaluation form and distilled what we're looking for into three things:

First, like most law firms, we're looking for intellect. Secondly, we want grit, and that's the aspect that I believe separates us from our peer firms. We want students who have looked adversity in the eye, overcome it, and shown the ability to persevere. Our clients expect greatness from us on very short deadlines, and we have found that those who have grit in their character work well here. Third, we're looking for leadership and interpersonal skills. We don't want people who can just do the job well, we want people who have depth of character, a good reputation for helping their community, for instance – people who you'd be proud to call one of your colleagues. We look for those three things a resume. When we invite candidates back to the firm, we're constantly asking ourselves if they have these three qualities.

CA: What other qualities are you looking for in a candidate?

BO: Cultural fit is really important. Every law firm has an identity. In general, large law firms pay similarly, and have similar offices, and similarly impressive clients—the thing that separates our firm is really the culture. Our attorneys are people that you're proud to be associated with and who you enjoy spending time with. That's the foundation of our recruiting philosophy: we want hard workers, but also people who you wouldn't mind sharing a beer with. As I said before, this job can be challenging at times—for that reason, we really value working with people we trust and respect and whose company we enjoy.

CA: What can students be doing now, for instance in their 1L summer, to increase their chances of impressing you at interview?

BO: The first year summer is a good chance for law students to do something interesting before they start on the BigLaw trajectory. Public sector experience a plus. For example, an internship at the SEC or DOJ is attractive on a resume. We look for anything that is a little different or interesting that gives students a different perspective when they come to us. People who have some prior work experience tend do very well here. With the recruiting schedule having become so compressed, we also like to start talking to students during their first year summer. At Winston we're going to be having receptions in our offices, taking students for lunch or coffee and starting to get to know them better in their 1L summer.

CA: How can someone stand out as a summer associate?

BO: We provide students with a lot of opportunities for work during the summer. We have a program where we let our billing partners write off a significant portion of a summer associates time. This enables partners to use summer associates for meaningful, engaging client work. When the cost element is taken out the equation, every case or deal team has something they want done, and that really enables opportunities for great work.

What I tell our summer associates is to focus as much on relationship building as the legal work. I always tell them: “You will come back to the firm, and the thing you'll really value is making connections, because success in a large law firm has a lot to do with sponsorship and mentorship.” The very best mentoring is natural and it starts as a summer associate. Those who have been successful here have relationships that they built in the summer that serve them well years later.

We really encourage students to try out different practice areas during the summer. After the first project, which is assigned, the system is completely self-directed. When students finish one project, they sit down with one of our summer committee members, and through our assignment database they can choose what to do next. It's a good system for helping people who aren't sure what they want to do; they can sift through the possibilities and have a better understanding of what is available.

CA: What is the firm doing to promote diversity in recruiting?

BO: We're doing several things. We've reconstituted our hiring committee recently, and there have been sweeping changes across the firm management. In the executive committee we've added more women and diverse attorneys, with an eye focused on having a diverse workforce. We go to some of the diverse job fairs, and we have a pretty clear objective that the firm's leadership has set: we have a goal of 20% or more diversity in our attorney ranks top to bottom. We also have a diversity scholarship that we've offered to three law students each year, who get $10,000 each for their third year of tuition. We're thinking of expanding that this year.

CA: Winston was once known for being fairly traditional and conservative, although the associates we spoke to said that is changing. Do you agree?

BO: The firm's had a historical reputation of having a conservative culture, but I think that's a bit unfair. We manage our financial affairs very conservatively, but that doesn't mean we're a conservative place to work. I've been here for 13 years and I've seen a shift into a much more relaxed environment. We have a jeans day every Friday, and in the Chicago office we closed our attorney dining room and built a café that's open to everyone, all staff and not just the attorneys. We have Friday happy hours that are really well attended, and we had a charitable event recently where we put spinning bikes in the café, and had people working out. Those are a few examples of how the firm has changed over time.

In addition, associates now have more influence over the firm's future and leadership than I've ever seen before. We have a really active associates committee which is an elected group across all offices and practice areas, and they regularly meet with the managing partner, myself, and other members of the firm's executive committee. We fully embrace the fact that today's associates are tomorrow’s partners and we try to treat people as such. We offer a really compelling proposition: a good conservative financial base, combined with a progressive, interesting and fun workforce. That represents a great opportunity for someone coming out of law school.

Winston & Strawn LLP

35 West Wacker Drive,
IL 60601-9703

  • Head Office: Chicago, IL 
  • Number of domestic offices: 9
  • Number of International offices: 9
  • Worldwide revenue: $818,300,000
  • Partners (US): 359
  • Associates (US): 381
  • Summer Salary 2016 
  • 1Ls: $3,461/week  
  • 2Ls: $3,461/week  
  • Post 3Ls: N/A
  • 1Ls hired? Yes  
  • Split summers offered? No  
  • Can summers spend time in overseas offices? No  
  • Summers 2016: 65  
  • Offers/acceptances 2015: 54 offers, 48 acceptances

Main areas of work
Litigation, corporate and financial, intellectual property, labor and employment relations, tax, employee benefits and executive compensation, energy, environmental, government relations and regulatory affairs, healthcare, maritime, real estate, trusts and estates.

Firm profile
Throughout its more than 160 year history, Winston & Strawn LLP has handled many significant, high profile matters for its clients – from antitrust litigation to cross-border mergers, energy transactions to labor negotiations. The firm is a global law firm with more than 800 attorneys across the US, Europe and Asia. The firm’s mission is to provide the highest quality legal services to meet the difficult legal challenges of the world’s most important companies and organizations. Winston & Strawn is consistently honored by its clients for outstanding legal service.

Recruitment details
• Number of 1st year associates: 54
• Number of 2nd year associates: 52
• Associate salaries: 1st year: $180,000
• 2nd year: $190,000
• Clerking policy: Yes

Law Schools attending for OCIs in 2016:
Please visit the Careers section of for a list of OCI Schools.

Summer details
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 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.