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.
Best Red Sox free agent contracts of the last 20 years: #2 - Adrian Beltré
Adrian Beltré might take top billing on this list had he been in Boston for more than one year. The Red Sox masterfully swooped in and took advantage of a soft market for the third baseman after a down year in 2009. They picked him up on a reasonable one-year, $9 million deal, and that 2010 season proved to be the springboard to a powerful back half of the Hall of Famer's career.
From 2010 to 2018, Beltré was worth 48.9 bWAR with the Red Sox and Rangers, outpacing his early-career numbers from 1998 to 2009 (44.6 bWAR) with elite-level production throughout his 30s. That all began with that stellar year in Boston.
Beltré played for 21 years and he only had one better year, at least in terms of bWAR, than he did in 2010. In 2010, the slugger led the league with 49 doubles along with 28 home runs, 102 RBI and a .321/.365/.553 slash line. He earned the first All-Star selection of his career to that point and his offensive exploits netted him the second Silver Slugger of his career, as well.
He parlayed that into a five-year, $80 million deal with Texas, and he wound up spending the rest of his career with the Rangers. But for one summer, Beltré was beloved by Red Sox Nation — and rightfully so.
Worst Red Sox free agent contracts of the last 20 years: #2 - Carl Crawford
Early in his career with Tampa Bay, Carl Crawford was a stud. A four-time All-Star, the speedster averaged 4.0 bWAR a season, led the league in stolen bases four times and put it all together in his final year with the Rays, bringing home a Silver Slugger and Gold Glove to set himself up for a massive payday in free agency.
Boston handed the outfielder a seven-year, $142 million deal on the heels of his monster 2010 season and things went sideways almost immediately. It proved that betting on a guy who made his name with his legs in his 20s attempting to maintain his athleticism into his 30s isn't the best idea.
His OBP fell below .300 in his first year in Boston and a historic September collapse from the club did little to endear their big-dollar outfielder to them. Due to a wrist injury, he didn't make his 2012 debut until mid-July and appeared in just 31 games before undergoing Tommy John surgery. Two days later, he was included in the blockbuster trade with the Los Angeles Dodgers that saw Crawford, Josh Beckett, Adrián González and Nick Punto head west in exchange for Iván De Jesús, James Loney, Allen Webster and two players to be named later.
That ended Crawford's Red Sox tenure, and if you ask any Boston fans, they'll tell you it was two years too long. A disaster from the start, this one is an all-time bust.
Best Red Sox free agent contracts of the last 20 years: #1 - JD Martinez
During the span of his five-year, $110 million deal with the Red Sox, JD Martinez was an All-Star four times, a Hank Aaron Award recipient, had a 135 OPS+ and helped Boston win a World Series championship. Not a bad return on investment for the club, eh?
Martinez got things started with a bang in 2018, his first season with the team, leading the league with 130 RBI and 358 total bases to go along with an OPS over 1.000. His 43 home runs were the most by a Red Sox player since Big Papi belted 54 in 2006. Boston put it all together as a club that year, winning 108 regular-season games before winning it all and vanquishing the Dodgers in the Fall Classic.
The next year, a relative 'down' season compared to the year prior, Martinez still hit 35 home runs, surpassed 100 RBI and posted a .939 OPS in 657 trips to the plate. He left no doubt: this guy was the offensive powerhouse the team had been searching for in the post-Ortiz era.
Martinez led the league with 42 doubles in 2021 and actually bested that mark in his final year with the Red Sox, racking up 43 two-baggers in 2022. In those five years with Boston, he established himself as one of the game's premier extra-base threats - and that contract proved to be worth every penny for the team.
Worst Red Sox free agent contracts of the last 20 years: #1 - Pablo Sandoval
Picking between Pablo Sandoval and Carl Crawford for the top spot on this list was a challenge, because both were complete dumpster fires in Boston.
A three-time World Series champion with the San Francisco Giants (2010, 2012, 2014), Sandoval hit the open market on the heels of the '14 title and signed a five-year, $90 million deal with the Red Sox. His free-swinging ways in his first year with Boston didn't go unnoticed and the fanbase soured on him quickly after he batted just .245/.292/.366 in 2015.
Sandoval was told to get in shape that winter and lose weight. He showed up to Fort Myers the following spring looking heavier than ever, denying anyone from the team told him to drop some pounds. His Red Sox tenure only worsened from there.
He tallied all of six at-bats in 2016 due to a shoulder injury, and although he returned to action the following spring, a 62 OPS+ and below-average defensive marks led Boston to designate him for assignment in July with more than three years still left on his contract. The Red Sox had to foot another $41 million after dumping him — one of the worst free-agent signings in recent memory.