Industry Insights From a Restructuring Powerhouse: A Conversation With Jamie Sprayregen

In the latest TMA Chicago Midwest Podcast episode, I sat down with James (Jamie) Sprayregen, Vice Chairman at Hilco Global. Jamie, a legend in restructuring and corporate reorganization, shared insights from his robust career, from his founding of Kirkland & Ellis' market-leading Restructuring Group to his current role at Hilco Global, where he aims to expand the firm's financial services platform, particularly in private credit.

First, we delved into Jamie's career trajectory and his approach to building a successful practice. Though he was initially interested in real estate law, Jamie shared that he found himself in the restructuring space by chance and then never looked back. His career took a serendipitous turn when he joined Kirkland & Ellis, where he built a world-renowned restructuring group through proactive hard work and relationship building, both of which are factors that Jamie believes are crucial for success in the legal field. Following his initial departure from Kirkland & Ellis before rejoining the firm three years later, Jamie co-headed the restructuring group at Goldman Sachs, which provided invaluable insights into leveraged finance and syndication, further enhancing his skill set and expanding his professional network. Along with the insights gained and lessons learned throughout his career, Jamie also highlighted the importance of creativity and commercial pragmatism when faced with new and challenging situations that require innovative problem-solving. 

Jamie went on to share macro trends in the restructuring industry, including the rise of liability management transactions and the increasing prevalence of private credit. He noted that the evolution of these trends is driven by market dynamics and regulatory changes, and discussed the shift toward out-of-court restructurings, which he views as a testament to the system’s efficiency. Jamie said that while he believes that financial restructurings are well-suited for out-of-court deals, operationally complex cases may still require formal bankruptcy proceedings.

Finally, Jamie emphasized the value of professional organizations like TMA in fostering relationships and providing opportunities for professional growth, and advised young restructuring professionals to stay persistent, focus on doing great work and build meaningful relationships. As a moderator for the upcoming TMA Chicago Midwest's 16th Annual Executive Speaker Forum, Jamie welcomed our listeners to send their questions for keynote speaker Bob Costas along to him in advance of the event. You can reach Jamie at jsprayregen@hilcoglobal.com.

Listen to the full episode below.