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
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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.