When you hear the words "Boston Red Sox" and "free agency," your mind immediately goes to the likes of David Ortiz, Manny Ramírez and Johnny Damon — the trio at the heart of the team that put the Curse of the Bambino to bed back in 2004.
And, really, who could blame you? Ortiz is one of the biggest free agent steals in the history of the game, Ramírez was an offensive juggernaut and Damon was the perfect table-setter for those big bats during his four years in Boston.
But what about the last 20 years? How have the Red Sox fared in free agency since then? It's been a mixed bag and now seems like a perfect time to revisit some of the wins and losses of the past two decades.
The best & worst Red Sox free agent contracts handed out in the last 20 years
Best Red Sox free agent contracts of the last 20 years: #3 - Nathan Eovaldi
After coming to Boston in a deadline deal with the American League East rival Tampa Bay Rays, Nathan Eovaldi decided to re-up with the Red Sox in the winter of 2018, inking a four-year, $67.5 million deal in free agency.
There will be a lot of fans in Boston who can't believe Eovaldi made this list, but when he was healthy and at his best, he was a difference-maker in the Red Sox rotation. It's hard not to look at his body of work in the 2018 postseason, when he helped Boston bring home its fourth World Series title since 2004. While he only captured that brilliance once more during the next four years, he still deserves mention.
Injuries were a major issue for the veteran, limiting him to just 116 innings during the first two years of the deal, although it should be noted the 2020 campaign, his second full season in Boston, was just 60 games long. On the heels of that shortened season, though, Eovaldi showcased what he was capable of, finishing fourth in AL Cy Young voting in 2021, leading the league with a 2.79 FIP and 1.7 BB/9 in 32 starts.
He closed out his Red Sox tenure in 2022, again battling injuries, but you have to factor in a largely successful (although imperfect) postseason resume when looking at his run in Boston. Health was an issue for much of this deal, but Eovaldi was a key piece of the puzzle during this era.
Worst Red Sox free agent contracts of the last 20 years: #3 - Masataka Yoshida
Boston wanted to make a splash in the international market and their answer was a five-year, $90 million pact with outfielder Masataka Yoshida prior to the 2023 campaign.
Despite finishing sixth in AL Rookie of the Year voting, Yoshida was, more or less, a league-average outfielder with some pretty glaring defensive deficiencies. He appeared in 140 games for Boston in 2023 and was worth just 1.4 bWAR while bringing home $15.6 million.
In 2024, manager Alex Cora made it clear how he felt about Yoshida, relegating him to the designated hitter role and keeping him off the field as a defender. The end result? He had another 1.4 bWAR year where he was a barely above-average offensive player. He's not a bad player by any stretch, but he's not worth the $90 million over five years, either.
The lack of growth from Yoshida is what's most alarming. By contrast, another Japanese outfielder who made the jump to MLB in recent years, Seiya Suzuki, has steadily improved year after year, going from 1.8 bWAR in his 2002 rookie season to 2.8 bWAR in 2023 and 3.5 bWAR in 2024. There doesn't seem to be any positive growth like that from Yoshida, whom the Red Sox still owe $55.8 million over the next three seasons.