McDonough, who looks like a distant relative Kennedy, was a keen sports fan. As a second-year student at Westwood High School in the suburbs of Boston, he gave a concert at the local WEEI sports radio station. At 16, his first day appeared and he was asked to drive the company van along Boylston Street to Fenway Park and hand out flyers.
"I did not want to tell him that I did not have my license," he said. "I just understood."
He arrived at Fenway that day, and ended up working on his promotion team's radio station, eventually installing microphones and cables for a famous Boston Globe sports reporter, who also happened to be called Will McDonough. As a freshman at Boston College, young McDonough began working for the Patriots, and after graduation he joined the full-time organization.
There, the 2002 graduate found himself working in the team's corporate affairs team, at the same time a lanky, the sixth round draw called Tom Brady was climbing the top of the NFL. McDonough won Brady's confidence, something that a former team-mate and current Tennessee Titans coach said was hard to do.
"We would see Will around Foxborough, he would say," Hey, you need help with anything? Do you want to get into this bar, or club? "- you just started to trust him in the course of time as a guy who was really trying to help, "said former All-Pro Patriots linebacker Mike Vrabel.
As Brady became a household name in New England, McDonough passed from the team's public affairs team to the first full-time quarterback manager. In the early days, the work was focused on making sure that Brady could concentrate on football after being "pushed into a whole new world of celebrities," McDonough said.
"I would like to tackle it only on non-football stuff one day a week," he said. "He matured me by negotiating sponsorship agreements for him from my own network."
Brady earns $ 8 million a year in sponsorships, according to Forbes' latest estimates. Among these is an Under Armor deal, which McDonough says he helped with the broker by introducing Brady to the founder and CEO of apparel maker Kevin Plank.
McDonough's network capacity was tested as he traveled the world to "Brady's hip" in 2005, which brought him that fateful evening to dinner at Nobu. He recalled joking with the billionaire and founder of Avenue Capital, Marc Lasry, about the absurdity of the list of Nobu guests and how "the guys like us" were the glue that got groups like that at the same table. That conversation impressed Lasry, who recruited McDonough on his own company in 2008.
"Will was deciding to change career and leave the Patriots, I convinced him to come with us," Lasry told CNBC.
With no bachelor's degree in economics (he was marketing and pre-law at Boston College), McDonough did an entry level job at the global investment company Avenue Capital, which had $ 9.4 billion of assets under management from February
"We ended up putting it in business development, and it turned out to be a great decision for our end," said Lasry. "For a guy who had not been in finance he did really well."