Last month, the Haslam family committed more than $300 million to launching an NWSL expansion franchise in Columbus. That deal included a $205 million expansion fee, a record for the women’s soccer league and a nearly 25% premium over the prior expansion team sold in Atlanta just last November.
The league’s stratospheric growth has been guided by Maddie Winslow, an investment banker with Inner Circle Sports who has overseen the NWSL’s recent expansion efforts. The announcement of the Columbus deal actually marked Winslow’s five-year anniversary at ICS, where she’s emerged not just as a trusted confidant to leagues and team owners, but as one of the leading deal advisers across women’s sports.
Three questions with Maddie Winslow
What’s something people miss about the growth of women’s sports? “Not all these properties in the women’s sports space are at the same point in their life cycle. One of my big things in women’s sports is that people treat them like a collective, since they have a collective tailwind, but these properties are very different. The structures are different and the growth opportunities are different.”
Are you spending time on women’s sports abroad? “We’re definitely paying attention; it’s just watching different dynamics. For instance, in European football, relegation completely changes how you look at an investment. Some women’s teams are tied to a men’s team, some are not. The tailwinds of women’s sports are being felt over there, too; it’s just a different structure.”
What lesson did you take from playing high-level ice hockey through college? “I always learned that the opportunity and exposure you get at an elite level, in anything you do, comes with sacrifice. If you’re not passionate about it, it’s probably not worth it. But if you are, it definitely is.”
When Winslow first arrived at the bank’s New York office five years ago, the NWSL was still selling expansion teams for around $2 million apiece.
“It’s pretty crazy to look back on. When we first got hired, it wasn’t something the industry was really talking about, or frankly had much data on,” Winslow said. “Now, it’s hard to have a conversation on high-growth opportunities in the sports ecosystem without it coming up.”
The path to preeminent dealmaker
Winslow grew up on Massachusetts’ North Shore playing field hockey, ice hockey and lacrosse. She excelled on the ice, winning four youth national championships before later earning All-American honors at Middlebury, where she studied economics and art history. Without a path to pro play at the time and little interest in coaching, Winslow put her focus on investment banking and spent her early career doing tech M&A work for AGC Partners and Jefferies.
Winslow hadn’t really considered a career in sports until she saw a post on LinkedIn from fellow Middlebury alum James Burke, then a banker with ICS. She recalled that a career at the intersection of sports and finance initially seemed too good to be true, but her outreach led to an interview and ultimately a role at the firm. She first worked on representing Marc Lore and Alex Rodriguez in their acquisition of the Minnesota Timberwolves.
“I definitely get exposure to everything we do, whether it’s sports tech, men’s sports deals, league deals, stadium financing deals,” said Winslow, who highlighted Austin FC’s stadium refinancing in 2022 and capital raise last year, as well as the sale of the Tampa Bay Lightning in 2024.
Though the Timberwolves deal included the WNBA’s Lynx, Winslow’s first full-time women’s sports assignment came when the NWSL hired ICS in 2022 to formalize the league’s expansion process.
“Maddie has played a critical role in helping us navigate a highly competitive expansion landscape.”
— NWSL Commissioner Jessica Berman
Winslow spearheaded that project and led the NWSL’s 2023 expansion round, which added Bay FC and Boston Legacy FC for a league-record $53 million apiece. Each expansion team sale since has blown away the prior deal’s record value. Last year, Winslow oversaw deals for expansion teams in Denver for $110 million and Atlanta for $165 million. Those were followed by Columbus at a $205 million valuation last month.
“Maddie has played a critical role in helping us navigate a highly competitive expansion landscape,” said NWSL Commissioner Jessica Berman. “She understands both the complexity of these transactions and the broader trajectory of women’s sports, and has been a trusted adviser as we’ve worked to bring in ownership groups that are committed to investing at the highest level.”
Shepherding the growth of women’s sports
ICS staffers don’t have formal titles, but Winslow has effectively made women’s sports M&A advisory a specialty practice. Beyond expansion, Winslow has worked on ownership transactions for the NWSL’s teams representing Chicago, New York and San Diego. She’s tight-lipped on other assignments in the space, given confidentiality agreements, but Winslow has also advised startup women’s leagues and buy-side bidders for women’s sports assets.
“Maddie has quickly become one of the most influential and trusted advisers in the NWSL and across the broader sports landscape,” said Ryan Dillon, Gotham FC’s chief business officer. “Her strategic insight, credibility with a wide range of stakeholders and relentless focus on delivering for her clients make her a truly invaluable partner — and a key force behind the continued growth of the NWSL.”
Looking ahead to the years to come, Winslow anticipates that her deal volume in women’s sports will remain robust, especially as an ongoing “cultural shift” leads to more young girls playing and caring about sports.
“That is one of those things that we’re not going to see the full impact of overnight, but in the next couple decades as that becomes the main consumer generation, the benefit economically that’ll have on women’s sports is going to be so huge,” Winslow said. “There is a lot of opportunity here, and I’m excited to play a role in what’s ahead.”
