In professional sports, the only thing worse than pinching purse strings is spending money stupidly. Unfortunately, halfway through this decade, a few Boston teams have already written their own cautionary tales via check book. Here are five contracts of the last five years that have aged like milk:
Trevor Story
Chaim Bloom’s big free agent signing has become the Red Sox’ heaviest albatross since the 2019 Chris Sale extension. Story signed a six-year, $140 million contract in 2022 after playing his entire career with the Colorado Rockies. His career in Boston has been marred by injuries, and he’s yet to play even 100 games with the Sox. His OPS this year is just .594. It hasn’t hit .800 in his Red Sox career, despite reaching those heights as a hitter five out of six years in Colorado. The Sox can’t exercise a club option until the 2028 – the final year of his deal.
Juju Smith-Schuster
One of Bill Belichick’s final free agent signings in New England was also one of his more boneheaded decisions because of its surrounding context. Patriots undrafted free agent project Jakobi Meyers had proven himself an adept volume receiver, but Belichick was happy to let him walk in free agency in 2023 to sign Smith-Schuster a three-year, $25,5 million contract. Smith-Schuster played in just 11 games and had 260 receiving yards and one touchdown. Meyers, meanwhile, continues to thrive on the Las Vegas Raiders. He had over 1,000 receiving yards last season.
Elias Lindholm
The Bruins made headlines signing 30-year-old Elias Lindholm to a seven-year, $54.25 million contract last summer. Boston needed to shore up its center position, and kudos to Lindholm for playing in every game of his debut season. Unfortunately, his productivity was miles behind his last complete season. In 2022, he scored 42 goals and 40 assists for the Calgary Flames over 82 games. In 2025, those numbers dropped to 17 goals for the and 30 assists for the Bruins. He also tallied 39 giveaways. With the Bruins fully entering a rebuild and still searching for a new head coach, the outlook for the future of this long-term contract isn’t great.
Devante Parker
The Patriots first acquired Parker in 2022,via trade, for 3rd and 5th round picks. That move was egregious enough for a team that’s been in a rebuild since 2020. But after a totally pedestrian 2023 season, (13 games, 539 receiving yards and three touchdowns), Belichick resigned Parker to two-year, $10.8 million extension. (In retrospect, the 2023 receiver moves may have been some of the worst decisions of Belichick’s career pertaining to any one position group – save the treatment his own 2023 quarterbacks). Parker played another 13 games and recorded 394 receiving yards and 0 touchdowns in what would be the final season of his NFL career.
Jonnu Smith
Watching the Jonnu Smith experience in Miami last season was one of the better Bob Lobel “Why can’t we get players like that?” moments in the 2020s. The tight end who recorded a career-high 884 receiving yards and eight touchdowns for the Dolphins in 2024 never showed his face in Foxborough, despite inking a four-year, $50 million deal in Belichick’s 2021 free agent bonanza. Smith, who looked totally lost at times in Josh McDaniels’ system, had just 294 receiving yards with the Patriots in Mac Jones’ rookie season, and one touchdown. He got even worse the following year, with 245 receiving yards and 0 touchdowns. Alas, he was worth just a seventh-round pick in a 2023 trade with Atlanta.