James Sterling

James Sterling has been at the forefront of Chicago corporate law for over two decades. After beginning his career at a top-tier national firm, he recognized that mid-market businesses deserved the same caliber of legal counsel available to Fortune 500 companies — without the prohibitive costs and impersonal service.

He founded Sterling & Associates in 2005, building a firm rooted in deep client relationships and strategic business thinking. James personally oversees the firm's most complex transactions, bringing a rare combination of legal precision and commercial pragmatism that clients consistently credit for their successful outcomes.

His M&A practice has encompassed transactions ranging from $5 million to $500 million across industries including technology, manufacturing, healthcare, and professional services. James is known for his ability to navigate multi-party negotiations, structure creative deal terms, and identify risks that other counsel often miss.

Beyond his transactional work, James serves as outside general counsel to several prominent Chicago companies, advising boards on governance, compliance, and long-term strategic planning. He is a frequent speaker at the Chicago Bar Association and the Executives' Club of Chicago on topics including deal structuring, corporate governance best practices, and business succession planning.