The team has won two MLR shields after defeating the San Diego Legion in 2023 and the Seattle Seawolves in 2024.

Early rosters from these matches included a mixture of veteran professional players from the disbanded PRO Rugby competition and top local talent from clubs such as the Boston Irish Wolfhounds and Mystic River.

NFL players Nate Ebner and Patrick Chung are minority owners of the Free Jacks.

On March 12, 2020, MLR announced the season would go on hiatus immediately for 30 days due to fears surrounding the COVID-19 pandemic.

The Free Jacks' first game of the 2021 season was played on March 20, facing LA Giltinis in Los Angeles.