Red Sox: 3 best and 2 worst trade deadline deals in franchise history

Houston Astros v Philadelphia Phillies
Houston Astros v Philadelphia Phillies / Mitchell Layton/GettyImages
3 of 3
Next

Things could certainly be going better for the Boston Red Sox in 2023. While we have been able to enjoy Boston thumping the Yankees on occasion recently, the reality is that the Red Sox have been at the bottom of the American League East for most of the season and the rest of the division seems to be good to very, very good. That creates an interesting dynamic heading into this year’s trade deadline.

On the one hand, winning the division seems all but out of reach as the Rays don’t seem to have much interest in losing much at all. However, a wild card berth isn’t out of the realm of possibility as the Red Sox are hanging around .500 despite a ton of setbacks in the first half.

As a result, what moves the Red Sox make (or don’t make) could be very consequential for their chances in the short-term and could end up being pivotal to the franchise for years to come. While most trade deadline deals end up being forgotten, a select few go down as moves that turn a team around and others make fans actively mad when you bring them up.

We don’t know what the future holds just yet, but we can look back at previous trade deadline moves and smile/get mad all over again. Here is a look at some of the Red Sox’s best and worst trade deadline moves in franchise history.

Best Red Sox trade deadline move: Adding World Series MVP Steve Pearce

This is a classic move that may not have given Boston a Hall of Famer for next to nothing, but gave them exactly what they needed at the right time and got them over the hump. Back in 2018, Boston was in need of a bat and made the move to acquire Steve Pearce from the Blue Jays for prospect Santiago Espinal.

To be clear, Espinal has been a pretty useful major leaguer for Toronto at times. However, Pearce would join Boston and go wild after the trade and end up winning World Series MVP and was a key reason that the Red Sox took home the title in 2018. He didn’t do much at all after that, but that doesn’t mean the trade wasn’t easily worth it.

Worst Red Sox trade deadline move: Trading Curt Schilling and Brady Anderson away

There is not a shortage of highlights from Curt Schilling’s time with the Boston Red Sox. In fact, there are exhibits in Cooperstown devoted to a couple of them. However, that was Schilling’s SECOND stint with the Red Sox and the first one did not end as favorably for Boston. Back in 1988, Boston traded the Baltimore Orioles Schilling and Brady Anderson for pitcher Mike Boddicker.

Boddicker was fine if unremarkable for Boston despite getting shelled by Oakland in the ALCS, but the “hindsight is 20/20” view of this trade is pretty brutal. Brady Anderson was a good player for Baltimore for over a decade including hitting 50 homers during the 1996. As for Schilling, he wasn’t a super highly regarded pitching prospect at the time, but he would end up becoming a very good pitcher with the Phillies and then forged a borderline Hall of Fame resume with the Diamondbacks and Red Sox as things came full circle.

Best Red Sox trade deadline move: The Nomar Garciaparra trade

You won’t find us slandering Nomar Garciaparra here as he was a very good player for a long time in Boston. However, the Red Sox were very close to being a real contender for a title in 2004 and while Nomar was hitting well when he was on the field, he was banged up and his defense left something to be desired. It wasn’t a great situation between him and the team by the time the trade deadline rolled around, so Boston worked a four team trade that ended up sending Nomar to the Cubs and brought Boston shortstop Orlando Cabrera and first baseman Doug Mientkiewicz.

Nomar would go on to be a productive hitter in the big leagues for the next six seasons or so, but the move got the job done for Boston. Mientkiewicz was pretty disappointing at the plate, but he was a good defender at first base and Cabrera was a stud in a Red Sox uniform. He hit close to .300 after the trade while playing strong defense at short and was a big reason why Boston took down the Yankees in that legendary ALCS in 2004. Nomar was (and is) missed, but the move was exactly what the Red Sox needed to finally win a World Series.

Worst Red Sox trade deadline move: Passing on Jeff Bagwell

Back in 1990, the Red Sox bullpen was a horror show despite the rest of the roster being very promising. Boston GM Lou Gorman (who was also responsible for the aforementioned Schilling/Anderson trade) felt like the correct move was to trade for the Astros’ Larry Anderson which made a lot of sense in a vacuum. To acquire him, Boston sent one of their top position player prospects to Houston. His name: Jeff Bagwell.

Yeah, that one hurts and is a lesson in why you should always hang on to bats you believe in and try to find a spot for them instead of valuing them less because they are “blocked”. Mo Vaughn was also a prospect at the time and while he was awesome, having him DH and Bagwell at first seems like it would have been….a much better option than what Boston did. Instead, Bagwell would end up being a Hall of Famer with the Astros and Anderson put together one decent half of a season with Boston before moving on to the Padres and Phillies. 

Best Red Sox trade deadline move: Derek Lowe and Jason Varitek solidify a World Series winning core

This one was a bit of a slower burn to pay off, but it would eventually turn into one of the best trades in Red Sox history. The Seattle Mariners needed help in their bullpen and for whatever reason, they wanted Heathcliff Slocum despite the fact that he had not been good that year. So, Boston was happy to send him to Seattle in exchange for Jason Varitek and Derek Lowe.

It is probably fair to say that the Mariners ended up having some buyer’s remorse without considering what they gave up in the trade too much. While he was marginally better the rest of the 1997 season than he was in Boston, it was still a 4.17 ERA and just 0.3 rWAR and the next season was worse as he put up a 5.32 ERA in 57 appearances which is decidedly not great. Slocum would bounce around after that with a few teams and while he had a decent season with St. Louis in 1999, he was pretty mediocre the rest of his career.

As for Boston, they had to be thrilled with what they got in return. From 1998 to 2004, Lowe would post a 3.73 ERA in 111 starts and finished in the top three of the AL Cy Young voting in 2002. He would end up being a very solid big league pitcher until his career came to an end in 2013. Jason Varitek would become a Red Sox lifer who went to three All-Star Games, won a Gold Glove, and was a critical part of Boston’s 2004 World Series-winning roster.

The lessons here: make sure you value your prospects properly, be wary of trading for relievers, and if a team wants to overpay for one of your mediocre relievers you should let them. 

More Red Sox news from BoSox Injection

manual

Next