A look back at Boston's most impactful November trades

November 16th, 2023

This story was excerpted from Ian Browne’s Red Sox Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

Instinctually, you are probably waiting for the Winter Meetings the first week in December to see what new Red Sox chief baseball officer Craig Breslow might have in store.

However, history tells us you might not need to wait that long.

Three of the most memorable and impactful trades in Red Sox history happened in the second half of November. Here is a look back, in chronological order.

Date: Nov. 18, 1997
The trade
: Red Sox acquire right-hander from the Montreal Expos in exchange for righty Carl Pavano and a player to be named later. The sides completed the deal on Dec. 18 when 19-year-old righty Tony Armas was the player to be named later.

The impact: Martinez was an up-and-coming ace for the Expos, having won his first Cy Young Award in 1997. In Boston, he turned into one of the best pitchers in MLB history. Every Martinez start at Fenway Park was an event, with Dominican flags waving and the K cards being posted to the scoreboard in center field. His masterpieces were numerous.

Making the deal even more impactful? The Red Sox signed Martinez almost immediately to a six-year, $75 million extension that included a $17.5 million option for 2004. Martinez’s overall body of work over those seven seasons with Boston? A 117-37 record with a 2.52 ERA and 1,683 strikeouts in 1,383 2/3 innings. The Sox played in the postseason in four of Martinez’s seven seasons. In 11 playoff outings, Martinez was 6-2. In 2015, Martinez was elected to the Hall of Fame on the first ballot.

Pavano went on to have a decent 14-year career, winning 108 games, but only 24 with Montreal. He did win a World Series with the ’03 Marlins pitching against the Yankees. Armas earned 48 of his 53 wins for the Expos/Nationals.

Bottom line: The trade was a landslide win for the Red Sox.

Date: Nov. 28, 2003
The trade
: Red Sox acquire right-hander from the Arizona Diamondbacks in exchange for left-hander Mike Goss, lefty Casey Fossum, righty Brandon Lyon and lefty Jorge De La Rosa.

The impact: As great as Martinez was, he couldn’t lift the Red Sox to that elusive World Series championship on his own. Enter Schilling, who gave Boston a co-ace combo. Schilling already proved what heights he could reach when paired with another all-time great when he and Randy Johnson combined to defeat the Yankees in the 2001 World Series. That gave Schilling instant credibility when he joined a Boston team that had won zero titles compared to New York’s 26 championships from 1919-2003.

Schilling came in with swagger, and backed it up, winning 21 games for the Red Sox in 2004. And when a tendon in his right ankle tore in the postseason, Schilling got an innovative procedure in which sutures were used to keep the tendon in place. The bloody sock was the stuff of legend, as the Red Sox first came back from a 3-0 series deficit to beat the Yankees in the American League Championship Series, and then swept the 105-win Cardinals in the World Series. For good measure, Schilling helped Boston to another title in his final season of ’07.

Red Sox general manager Theo Epstein pulled off a true heist. Goss never made it to the Majors. Fossum had a 5.45 ERA in nine seasons. Lyon had a nice career, pitching in 572 games over 12 seasons. De La Rosa wound up being the best player Boston sent over in the deal, winning 104 games over 15 seasons. Unfortunately for the D-backs, only three of those wins came for their franchise.

Bottom line: Another steal for the Red Sox.

Date: Nov. 24, 2005
The trade
: Red Sox acquire right-hander , third baseman , righty Guillermo Mota from the Florida Marlins in exchange for shortstop , righties Aníbal Sánchez, Jesús Delgado and Harvey Garcia.

The impact: Beckett was the top target for this trade for the Red Sox, who needed another front-line pitcher as Schilling was starting to age. Lowell, who had a brutal season in 2005, was viewed as a throw-in. That view wound up wrong. Lowell (World Series MVP) and Beckett (20 wins in regular season, ALCS MVP) were equally important to a 2007 Boston team that won it all. In that magnificent playoff run, Beckett went 4-0 with a 1.20 ERA. Beckett pitched for the Red Sox from ’06-12. Lowell, a Red Sox Hall of Famer, was a core member of the club and a Fenway favorite from ’06 until his retirement after the ’10 season.

Bottom line: A good trade for both teams. Ramirez,  Boston’s best prospect at the time of the trade, became an instant star for the Marlins, winning the National League Rookie of the Year Award in 2006 and the NL batting title in ’09. Ramirez wound up back with the Red Sox for four seasons late in his career and was a key cog in the club’s ’16 AL East championship squad. Sánchez won 116 games over 16 seasons --  44 of them for the Marlins. He led the AL in ERA for the Tigers in ‘13, but the Red Sox beat that Detroit team in the ALCS.