He was told he would be “litigating tractor pulls.” He chose Rockford anyway and has never looked back.
When Tim Rollins told his Army commanding officer he was leaving behind offers in Washington, D.C. and other major markets for an opportunity in Rockford, Illinois, the response was not particularly supportive. His CO told him he’d be wasting his talent and litigating tractor pulls. However, within six months of starting at WilliamsMcCarthy LLP, Rollins was helping unwind a joint venture between a Rockford-based company and a Japanese firm for a factory in Tennessee.
That was more than 30 years ago, and he’s still here.
Rollins is no stranger to the Midwest. He grew up in Mendota, Illinois, the son of a Canadian immigrant who left school after eighth grade. As the first male on his father’s side of the family to ever attend college, he was awarded a federal four-year ROTC scholarship to the University of Illinois. On graduation, he deferred his military service to attend law school. He applied to Harvard, University of Chicago, and University of Virginia, all of which accepted him.
Ultimately, the prestige of Harvard and the allure of New England won out. At Harvard, Rollins continued to excel, becoming an editor of the Harvard Law Review – a distinction he is careful not to overstate. “There is a board of editors. I wasn’t the Editor-in-Chief.”
He does, however, share that he served with a law student one year behind him – Supreme Court Justice Elena Kagan. Rollins quips, “I knew her, but I’m sure she doesn’t remember me.”
When sharing the impact his time at Cambridge made on his practice of law, Rollins reveals that Harvard Law School isn’t about training you to be a practicing lawyer – it’s about training you to think.
The Pentagon and the Personal Computer
After graduation, Rollins fulfilled his Army commitment and went on active duty, being stationed at the Pentagon doing government contract work. While the line on his resume is impressive, he shares that it was not glamorous.
“The first office I was in was in a part of the building that was not on the tour. We had rats running through our office. My second assignment was in the Office of the Judge Advocate General’s Contract Law Division. That was a nicer office, but it was in the part of the Pentagon that was obliterated on September 11, 2001.” The work, in hindsight, was hugely consequential.
This was the early days of personal computing, and Rollins was a contract attorney for an agency that handled contracting for the Secretary of the Army, the Secretary of Defense, and the Strategic Defense Initiative Organization – Star Wars. He also served as the contract attorney for contracts involving a legendary DoD entity: Defense Advanced Research Projects Agency, or DARPA. “That was the cool stuff,” he acknowledges.
One of his assignments was to serve as the contract attorney for the first-ever office-wide automation contract for the Office of the Secretary of Defense. Another assignment involved attempting to get the Army National Guard to allow competition for its national marketing contract after years of awarding contracts to a sole-source vendor. Rollins discovered that documents had been falsified in an attempt to justify awarding a contract to the preferred vendor, resulted in the forced retirement of a brigadier general and the convening of a court-martial for one of the other individuals directly involved.
Midwest Calling
When his service was completed, Rollins had offers from D.C. and other big-city firms. Having spent years dealing with urban commuting, he knew that he wanted something different than a life organized by time spent in traffic. He wanted space to grow and room to breathe. Being there for soccer games, fall concerts, and parent-teacher conferences would matter, so he looked at returning to the Midwest, and specifically Rockford.
He sent letters (actual letters) to every law firm in town with more than five attorneys and got responses from each one. He interviewed them as thoughtfully as they interviewed him, and when it came time to choose, he landed on WilliamsMcCarthy. Part of it was the people and the firm’s culture. The other part was how they answered one question he asked every firm: could he have his own personal computer? They said it would be on his desk the day he arrived. “They were a leader,” he says simply.
What Stayed, What Has Changed
More than a quarter century later, Rollins has been a part of the firm’s continued growth and ongoing commitment to the community. He’s seen changes to local businesses as well as the expectations for practicing law.
As an example, he shared a story from Jack McCarthy, one of the firm’s founders, who lamented that the fax machine had ruined everything – it introduced the demand for immediate receipt and quick replies compared to sending correspondence by mail.
“I think about that story more now,” reflects Rollins. “The next iteration was email. And now some clients text us.”
He worries about what that means for younger attorneys and the temptation to lean on technology for speed when sometimes the situation requires slowing down to think. While not a technophobe – he was using personal computers before most law firms even owned one after all – he does caution that excellent representation requires more. “That’s what people are paying us to do: to think.”
Outside the Office
The firm’s commitment to the community was also something Rollins took seriously. He’s been on more boards and committees than he can quickly list, including Family Counseling Services, the Center for Sight and Hearing, the Discovery Center Museum, the Dean’s Council for the University of Illinois College of Medicine, the Rockford Chamber of Commerce and others. No more deeply has the community felt his contributions than in his time on the Rockford Public Schools Board of Education, on which he served for 12 years. During his tenure, the district navigated operational turbulence, a ransomware attack, and then, in 2020, the global pandemic.
He’s candid about the challenges and his contributions. “We made some progress. On the operational side, things run a lot better.” He also acknowledges there is still work to be done to reach the student achievement milestones he’d like to see – an honest assessment from someone who took the work seriously and doesn’t like spin.
What’s Next
Today, Rollins is happy to focus on what he does best – helping businesses navigate the complexities of transactions. His CO was wrong about the tractor pulls. His work at WilliamsMcCarthy – and contributions to the community he continues to choose – is anything but small.
Timothy Rollins, a partner with WilliamsMcCarthy LLP, attended the University of Illinois and received his B.A. in Political Science, magna cum laude, in 1982. He graduated from Harvard Law School, magna cum laude, in 1985, where he served as an editor of the Harvard Law Review. He can be reached at trollins@wilmac.com or (815) 987-8942.
