McDonough, who looks and sounds like a distant Kennedy relative, was a sports buff as a boy. As a sophomore at Westwood High School in suburban Boston he landed a gig at local sports radio station WEEI. At 16 years old, he showed up on his first day and was asked to drive the company van down Boylston Street to Fenway Park and hand out flyers.
“I didn’t want to tell them I didn’t have my license,” he said. “I just figured it out.”
He made it to Fenway that day, and ended up working at the radio station on its promotions team, eventually setting up microphones and running wires for a famous Boston Globe sports reporter, who also happened to be named Will McDonough. As a freshman at Boston College, the younger McDonough started working for the Patriots, and after graduation joined the organization full-time.
There, the 2002 graduate found himself working in the team’s corporate affairs group at the same time a lanky, sixth-round draft pick named Tom Brady was ascending to the top of the NFL. McDonough won over Brady’s trust, something a former teammate and the current coach of the Tennessee Titans said was hard to do.
“We’d see Will around Foxborough, he’d say, ‘Hey, you need help with anything? Do you want to get into this bar, or this club?’ – you just start to trust him over the course of time as a guy who was really looking to help,” said former All-Pro Patriots linebacker Mike Vrabel.
As Brady became a household name in New England, McDonough transitioned from the team’s public affairs group to the quarterback’s first full-time manager. In the early days, the job centered around making sure Brady could focus on football after being “thrust into a whole new world of stardom,” McDonough said.
“I would only approach him on non-football things one day a week,” he said. “It matured into me negotiating sponsorship deals for him from my own network.”
Brady makes $8 million a year in sponsorships, according to Forbes’ latest estimates. Among those is an Under Armour deal, which McDonough says he helped broker by introducing Brady to the apparel-maker’s founder and CEO, Kevin Plank.
McDonough’s ability to network was tested as he traveled the world “on Brady’s hip” in 2005, which brought him to the dinner at Nobu that fateful evening. He recalled joking with billionaire and Avenue Capital founder Marc Lasry about the absurdity of the Nobu guest list and how “guys like us” were the glue that got groups like that at the same table. That conversation made an impression on Lasry, who recruited McDonough to his own firm in 2008.
“Will was deciding to change careers and leave the Patriots, I convinced him to come join us,” Lasry told CNBC.
With no economics degree (he was marketing and pre-law-at Boston College), McDonough took an entry level job at the global investment firm Avenue Capital, which had $9.4 billion of assets under management as of February.
“We ended up putting him in business development, and it turned out to be a great decision on our end,” Lasry said. “For a kid who had not been in finance he’s done really well.”