’s ranking of the best free-agent signings in MLB history puts two of the Red Sox’s biggest gambles near the top, with David Ortiz and Manny Ramirez both making the kind of impact that changes a franchise. The list, compiled by Bradford Doolittle, comes 50 years after free agency began and spotlights how Boston got elite production from two very different stars.
Ortiz arrived in 2003 on a one-year, $1.3 million contract after the Twins let him go at age 26, even though he had just posted his best season with 20 home runs and a 120 OPS+. In Boston, he answered with a.288/.369/.592 line and 31 home runs in his first of 14 seasons, finished fifth in AL MVP voting, and eventually hit the second-most home runs in Red Sox history with 483. He also helped the club win three World Series titles and carried a.947 career postseason OPS, a postseason résumé that few sluggers in history can match.
Manny Ramirez came first, signing before the 2001 season to an eight-year, $160 million deal that turned into one of the great bargains in hindsight. He hit.312/.411/.588 during his Red Sox tenure, made eight straight All-Star appearances, won six Silver Slugger awards and helped Boston win two World Series titles. Ramirez lasted 7½ years of the deal before being traded to the Dodgers in 2008, but the stretch was long enough to leave him right beside the game’s great hitters in franchise history.
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That judgment is reflected in Doolittle’s ranking, which places Ramirez alongside Ted Williams, Tris Speaker, Jimmie Foxx, Ortiz and Wade Boggs in terms of OPS+. He described Ramirez as “Manny being Manny,” but said the slugger ranks with the best hitters ever to play for the franchise. On Ortiz, Doolittle noted that he was not a free agent because he reached a service-time threshold, but because Minnesota released him despite that breakout season, and that he kept re-signing and extending in Boston until he reentered free agency after the 2011 season.
The Red Sox connection is what makes the ranking linger. Boston landed two of the best pickups in the history of free agency two years apart, then watched both players become central figures in a dynasty. The same list also nods to more recent risk-reward moves, including Aroldis Chapman, who paid huge dividends for the Red Sox last year, and Ranger Suarez, who has allowed four runs in each of his first two starts to begin a $130 million contract.
For a club built as much on stars as on scouting, the lesson is plain: Boston’s best free-agent wins were not minor upgrades. They were the kind that altered October, filled the ballpark and, in Ortiz’s case, never really ended.
