The Best & Worst Trades at the MLB Trade Deadline in Red Sox History

The Best & Worst Trades at the MLB Trade Deadline in Red Sox History
Fact Checked by Thomas Leary

With the Aug. 2 MLB trade deadline looming, the Boston Red Sox struggled throughout the month of July, putting up a paltry 8-19 record, including a sizeable losing streak that took them out of playoff contention in rapid fashion. 

That losing streak, combined with the New York Yankees season-long dominance and the Toronto Blue Jays heating up in the latter half of July, has all but put a nail in the coffin of Boston’s season and sees it heading into the trade deadline as sellers, a position that this storied franchise isn’t overly comfortable being in. 

While the Red Sox are only three and a half games back of a Wild Card spot, they are the last of seven teams in the mix for the final three playoff spots.

Massachusetts sportsbooks have seen the Red Sox decline and adjusted their numbers on the oddsboard, and Boston now sits at +9000 to win the World Series and +25000 to stage a miracle comeback and win the AL East Division.

Up for grabs following the trade of catcher Christian Vazquez are another two key members of the Red Sox 2018 Championship squad, most notably J.D. Martinez. Martinez had two doubles in what is likely to be his final home game at Fenway Park in a 7-2 win over the Milwaukee Brewers on Sunday afternoon. 

Starting pitcher Nathan Eovaldi is also likely to be dealt as the Red Sox look to fill some holes and add to their prospect base in hopes of a quick turnaround in a strong AL East division.

Despite having an opt-out clause in his contract after this season, star shortstop Xander Bogaerts has been told by club management that he will not be dealt. He and Rafael Devers appear to be a big part of the clubs plans going forward.

Varitek, Lowe Helped Bring Title To Boston

Trade on July 31, 1997 Total WAR of Acquisitions
⚾️ Red Sox receive P Derek Lowe & C Jason Varitek43.7
⚾️ Mariners receive P Heathcliff Slocumb-.02

The Best Trade in Red Sox Deadline History

While this year's trades won’t be able to be judged anytime soon, the Red Sox have certainly had success in a similar position in the past. 

The most notable trade that worked resoundingly in their favor was the 1997 deadline move with the Seattle Mariners. The Mariners were looking to strengthen their bullpen and Boston sent them Heathcliff Slocumb in exchange for young catcher Jason Varitek and starter Derek Lowe. 

The trade didn’t pay off immediately, but these two players were key members of the 2004 championship team and spent the better part of a decade as key members of a consistently contending Red Sox club.

Using the website to breakdown the analytical impact of the trade makes a strong case that this was the best trade deadline acquisition in Red Sox history. 

Varitek and Lowe combined to add 43.7 Wins Above Replacement (WAR) in their time with Boston, while Slocumb had a negative effect on the Mariners with a -0.2 WAR in his time there.

Boston also went into their 2004 championship run on the heels of another successful trade, sending star shortstop Nomar Garciaparra out the door in exchange for two key members of their World Series squad in Orlando Cabrera and Doug Mientkiewicz.

Jeff Bagwell: The One Who Got Away

Trade on Aug. 30, 1990 Total WAR of Acquisitions
⚾️ Red Sox receive P Larry Andersen 1.2
⚾️ Astros receive 1B Jeff Bagwell79.9

The Worst Trade in Red Sox Deadline History

Not all trades have their desired impact, and that was the case in 1990 when Boston sent future hall of famer Jeff Bagwell to the Houston Astros for relief pitcher Larry Andersen. 

Andersen only made 15 appearances for the Red Sox, adding 1.2 WAR over his time there while Bagwell transformed from an average prospect into a perennial All Star who hit 449 home runs and added 79.9 WAR over his tenure with the Astros.

Trading a future All-Star like Bagwell is unlikely this year, as the Red Sox are more interested in acquiring young players. Getting a haul like they did with Varitek and Lowe in 1997 would have an incredibly positive effect on the team for the next decade. 

With players like Martinez aging and no longer a part of the team's future plans, this is the perfect time to try and land some solid prospects to have another run like they did in the early 2000’s.

Massachusetts Sports Betting Officially On Its Way

The MLB trade deadline comes as the state legislature finally reached a deal to make legal, regulated sports betting in Massachusetts a reality. 

The bill will allow betting on pro sports for those over 21 and includes provisions for retail and Massachusetts betting apps.

Four of the five states that border Massachusetts — New Hampshire, Rhode Island, Connecticut and New York — have live and legal online sports betting.

Over the past several weeks, a legislative committee had met to hammer out the differences in two sports betting bills. Now after reaching a compromise, Massachusetts could become one of the nation’s most competitive markets.



Cecil Peters is a Senior Betting Analyst for A professional sports bettor in Canada, Cecil specializes in analyzing the latest odds impacting professional sports teams across North America.

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