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Sterling is a corporate attorney who guides clients through both major transactions and day-to-day business matters. Private companies, family offices, private equity firms, strategic buyers, and independent sponsors rely on his smart, steady advice as they navigate complex decisions.

In his transactional practice, Sterling handles lower middle-market and middle-market mergers, acquisitions, joint ventures, and more. He leads due diligence review, drafts core documents, and negotiates agreements for both buy-side and sell-side deals. Whether Sterling is representing a large private equity firm or an independent sponsor building its reputation, he commits to understanding his client’s priorities and driving the full life cycle of the transaction with his client’s goals in mind.

Sterling also acts in an outside general counsel role for some clients, serving as a trusted advisor with a pulse on the market and deep business experience. His knowledge of structuring matters, operations, corporate governance, and more positions him as a valuable resource for entrepreneurs and investors building their businesses and portfolios.

A born-and-raised Chicagoan with four degrees from Northwestern University, Sterling is an active alumnus who is ingrained in the community. In his undergraduate tenure, he served as captain of the university’s men’s varsity basketball team. His passion for athletics inspired him to develop a sports law practice focused on contract negotiations.

Much More Than My Work

I’m a proud Northwestern University alumnus, and I stay actively involved, having served as a co-chair for the Class of 2008’s 10-year reunion and a board member for the 15-year reunion. I’ve also served as an interviewer on the Admissions Council for Northwestern University’s Kellogg School of Management for seven years.

In my free time, I like both playing and watching basketball. I cheer for both the Chicago Bulls and the Chicago White Sox, and I particularly love following the journeys of individual athletes.

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