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Inside Former NFL First-Round Pick Gosder Cherilus' Uphill Climb Into Commercial Real Estate

Breaking into Boston’s tight-knit commercial real estate community is a tall task, even for a local football hero.

Gosder Cherilus in his Seaport office.

Retired NFL offensive lineman Gosder Cherilus may be best known for his role on Boston College’s breakout 2007 team, when the 6-foot-7, then-316-pound tackle blocked for star quarterback Matt Ryan. He named his first development company Eagle Development Partners as a nod to his alma mater.

Today, Cherilus and his new company, Bastion Cos., are joint venture partners on 10 World Trade, a 600K SF office and lab development in the Boston Seaport. Cherilus serves as a project manager on the Boston Global Investors-led project. 

The development, his first major joint venture, comes nearly a dozen years after he first began to mull real estate as a post-NFL investment and career opportunity. 

Cherilus was born in Haiti, but his family immigrated to Boston and he went to Somerville High School, taking summer jobs at construction sites. Those sites are where he took an interest in the industry, listening to workers talk about the value and scarcity of real estate. 

After he started a BC-record 51 straight games — including all 13 for the 2007 team, which ended the season ranked No. 10 in the country — the Detroit Lions drafted Cherilus 17th overall in 2008 and signed him to a $15M rookie contract. Financial advisers entered Cherilus’ life as he sought to invest his new money, but he said he didn’t know who to trust.

“One of the things I wanted to do was to start investing into real estate, buying homes, establishing relationships with banks,” a slimmed-down Cherilus said in his Seaport office this week. “[I thought], hopefully by the time I retire, those will be almost paid for and I can actually really retire and start to have some sort of cash flow going on and create some work life after football for myself.”

Gosder Cherilus with the Detroit Lions in 2011

Cherilus thought he found his first opportunity when he was set to buy a 20-unit apartment building in Malden, a few miles from his adopted hometown of Somerville. Cherilus was eager to close, but realized late in the process that the property had previously flooded, and the deal fell through. Following that experience, Cherilus decided to form his own real estate entity, Eagle Development Partners. 

Following the recommendation of industry colleagues, Cherilus moved to certify his firm as a Minority-Owned Business Enterprise. He attended NAIOP workshops, learned about joint venture partnerships and said he was inspired to think bigger and seek contracts with larger industry players to help his company grow. 

“We were doing that for about four or five years, but we couldn't get any jobs,” Cherilus said. “You know, it was just tough.”

He heard praise from potential partners about his pitches and his company, but was often rejected because of concerns over Eagle’s résumé or simple lack of opportunities on projects, he said. 

“I decided, you know what, I wasn’t going to keep going after some of these contracts,” Cherilus said. “I was going to go back to doing what I know, which was build some smaller apartments anywhere between eight to 16 units.”


All the while, Cherilus was enjoying a career as a stalwart offensive lineman. He played games across nine seasons in the NFL, blocking for some of the league's top quarterbacks in the Lions’ Matthew Stafford and the Indianapolis Colts’ Andrew Luck. He retired in 2017 after a stint with the Tampa Bay Buccaneers, then his real estate activity picked up.

Eagle started developing apartments in Allston, Brighton and Woburn and secured permitting for a 269-unit market-rate community in Quincy, which it sold to Dolben Cos. in 2018. The firm was on the verge of a partnership on an 87-acre project in Kennebunkport, Maine — what would have been Cherilus’ largest project to date — but it fizzled when his team didn’t agree with some of the aspects of the partnership, he said. 

A rendering of 10 World Trade Boston, right, in the Seaport.

Cherilus’ struggle to gain major traction wasn’t unique — minority-owned firms secured 1% of the $2.1B in contracts for construction and professional goods and services during the first term of Mayor Martin Walsh’s administration, a February report revealed.

Cherilus sought mentorship from prominent Black Boston developers like Richard Taylor and the late Kenneth Guscott, a fellow Caribbean. Cherilus said there is a healthy professional network of Caribbeans in Boston, including Haitians.

“When you talk about Haitians, you have some of the most resilient, hard-working people in the world,” he said. “It was just good to see some of these opportunities finally being provided to people who deserve them.”

He said his allies in the real estate industry didn’t come from the NFL, but rather his BC alumni network. Playing for one of the best teams in school history helped with visibility, Cherilus said, and there weren’t many rooms he walked into that didn’t include a fellow Eagle.

Cherilus attended BC with John Hynes IV, the son of Boston Global Investors CEO John Hynes III. It was Hynes IV who sold Cherilus on the joint venture for 10 World Trade, at a time when Cherilus said he was thinking about leaving real estate and getting into coaching. Hynes IV didn't respond to requests for comment this week.

BGI also partnered with minority-owned Cogsville Group, and the Massachusetts Port Authority awarded development rights to the group in 2018. The Boston Planning and Development Agency approved the project last August.

Cherilus serves as the project manager for diversity and inclusion efforts, and he has focused on working with minority-owned subcontracting companies. He wants smaller MBE like himself to get a foot in the door and grow, like his own firm did.

“Show up with a joint venture contract or partnership, bring a minority-owned company with you,” Cherilus said, in a message to developers. “That way they can work with you, learn with you, learn from you, and they can start being a little bit bolder.”