Boston’s Best Bets: The Greatest Free Agent Signings of the 2000s

Since the turn of the millennium, the Boston Red Sox have inked some unforgettable free agent deals. While not all have panned out, several have proven to be history-changing decisions that brought championships to Boston. Here are the five most impactful free agent signings by the Red Sox since 2000.

1. David Ortiz (2002 Offseason)

Arguably the greatest signing in Red Sox history, David Ortiz transformed from an under-the-radar acquisition into one of the franchise’s all-time greats. Originally signed to a one-year deal after being released by the Minnesota Twins, Ortiz quickly made his mark. "Big Papi" was the heart and soul of the Red Sox for over a decade, leading the team to three World Series titles (2004, 2007, and 2013) and establishing himself as one of the best clutch hitters in baseball history. His postseason heroics, especially in 2004 and 2013, cemented his status as a true Boston legend. We have Minnesota to thank, but also Pedro Martinez, who pleaded with the team’s management to give Ortiz a chance after the Twins cut him. With Boston, Ortiz hit a mind-boggling 483 home runs and drove in more than 1,500 runs, all while batting a very respectable .290.

2. Johnny Damon (2001 Offseason)

When the Red Sox signed Johnny Damon to a four-year, $31 million contract before the 2002 season, they were looking for a spark at the top of their lineup — and Damon delivered. His speed, solid defense, and superb ability to get on base made him a perfect fit for Fenway Park and an essential catalyst for Boston's offense. Damon played a crucial role in the 2004 World Series run, particularly in Game 7 of the ALCS against the Yankees, when he hit two home runs, including a grand slam. His energetic, scrappy style of play made him a fan favorite and a key figure in ending Boston’s 86-year championship drought. Unfortunately, he may be remembered poorly by some due to his turning to the dark side and joining the Yankees after his contract expired. Damon racked up 730 hits in his four years with Boston, batted .295, and drove in nearly 300 runs. He swiped 98 bases to boot.

3. Manny Ramirez (2000 Offseason)

The Red Sox made major waves when they signed Manny Ramirez to an eight-year, $160-million contract in 2000, one of the richest deals in baseball at the time. While Ramirez’s tenure was often tumultuous off the field, there’s no denying his production on the diamond. Ramirez was a key piece in the middle of the Red Sox lineup, hitting for both power and average. Ramirez and Ortiz quickly became a dynamic slugging duo, terrorizing the league together. His performance in the 2004 postseason, where he was named World Series MVP, remains one of the high points of his career. In eight years with Boston, Ramirez ran a batting average of .312, launched 274 round-trippers, drove in 868 runs, and racked up over 1,200 hits.

4. J.D. Martinez (2017 Offseason)

When the Red Sox signed J.D. Martinez to a five-year, $110 million contract in the 2017 offseason, they were banking on his ability to be a difference-maker in their lineup—and he delivered in spectacular fashion. Martinez’s impact was immediate, leading the team in both home runs and RBIs while posting one of the best offensive seasons in franchise history (.330/.402/.629 with 43 home runs and 130 RBI). His presence powered the Red Sox to a franchise-record 108 regular-season wins and culminated in a World Series championship. Martinez’s ability to hit for power and average helped anchor the Red Sox offense for multiple seasons before departing in 2023. Martinez launched 130 home runs with the Sox while registering 430 RBI. He batted .292.

5. Keith Foulke (2003 Offseason)

While often overlooked, Keith Foulke was a critical component of the Red Sox's 2004 World Series run. Signed to a three-year deal before the season, Foulke provided much-needed stability to the bullpen as the team’s closer. His performance in the 2004 postseason, where he saved crucial games and closed out the final inning of the World Series, was pivotal to the Red Sox’s success. Foulke’s contributions in high-pressure situations were vital, making him one of the most underrated yet essential free agent signings of the 2000s. During his three-year tenure in Beantown, Foulke registered a 13-9 record along with 47 saves and an ERA of 3.73.

An honorable mention goes to southpaw thrower David Price, who inked a seven-year, $217 million deal in December of 2015. Price had an up-and-down tenure with the Sox, but he ultimately helped them take home the 2018 World Series with a handful of masterful starts in that postseason. In four years with the ballclub, Price compiled a record of 46-24, struck out 609 batters across 588 innings, posted a 3.84 ERA, and had a highly-publicized altercation with Dennis Eckersley.