The group of about a dozen Yale alumni, internally dubbed the “Fight Club,” has so far raised about $5.5 million for DeSantis from their contacts, according to the campaign. They meet for 45 minutes each week to discuss strategy and fundraising outreach. DeSantis, who graduated from Yale in 2001, joins the calls about once a month. 

Michael McClellan, a partner at law firm Newmeyer Dillion and one of DeSantis’s Yale classmates, organized the group back in March, months before the governor formally launched his presidential bid, and has since led multiple California fundraisers in June and September. It raised more than $1 million from those events, McClellan said.

The Fight Club is the DeSantis network’s take on what is called bundling in political circles. Affluent and well-connected supporters willing to recruit their friends to give are known as bundlers — and they’re critical to many candidates’ fundraising efforts. 

Federal campaign contribution rules limit individuals to give only $6,600 to a candidate. Bundling several smaller donations into a larger gift from multiple people gives the donors greater access to the candidate.

“The best part of this is seeing our college classmates and teammates raising money and growing support from their networks across the country — especially the people who haven’t participated in politics before,” McClellan said. 

Cash on hand

DeSantis’s campaign has been beset by money troubles over the past several months. At the end of September, the campaign had about $5 million on hand for the primary, well behind the funds former President Donald Trump and former United Nations Ambassador Nikki Haley have amassed. A DeSantis campaign official said the governor raised an additional $1 million since the start of October.

DeSantis has also failed to make any significant gains on Trump’s lead in the polls. But the alumni group is focused on ensuring the campaign has money consistently coming in, not on the polling, said Sudha Reddy, founder and managing principal of Haven Realty Capital. 

“Unlike others who may be getting swayed by polls or are waiting for something, it doesn’t really affect us,” said Reddy, one of DeSantis’s fraternity brothers and baseball teammates.

The Yale alumni are continuing to assist with more fundraisers this fall. Already on the calendar is one at the end of October in Miami, ahead of the third Republican debate on Nov. 8, which is scheduled to take place in the same city.

“Some of my closest friends that I’ve had for 20, 25 years, they are killing it for me raising money,” DeSantis said in an interview on Fox News in October. “I mean it’s really, really cool to have guys I was in college with playing baseball that are now here as part of this.” 

Other investors

Other Fight Club members include the governor’s fraternity brother Nick Sinatra, founder and chief executive officer of real estate firm Sinatra and Co. and a former George W. Bush administration official, who helped organize events in New York, Pennsylvania and Connecticut. Fellow fraternity brother Tom Gioia, a private equity investor with Hemlock Partners, planned a cocktail reception in early October for other wealthy investors.

Matthew Schmidt, a member of the group who is the chief executive officer at the Brewery in Milwaukee, hosted an event after the first presidential debate in August. Schmidt said he always votes, but before DeSantis, he questioned whether donating to political candidates actually made a difference.

“It’s easy for me to have that conversation with somebody else who hasn’t donated before,” Schmidt said. “I can tell them ‘hey, it’s not scary, don’t worry. It’s a great campaign and you’re doing something that can help the country.’”