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Who is your favorite trade deadline acquisition in Red Sox history?

July 31, 2025 by Over the Monster

MLB: Boston Red Sox at Kansas City Royals
Jay Biggerstaff-Imagn Images

Eovaldi? Pearce? Someone from the Nomar trade? Fernando Abad? Other?

With the trade deadline just a matter of days away, the OTM team would like to take you on a trip down Memory Lane. Who, would you say, is the best player that the Red Sox acquired at (or around) the trade deadline? Or your favorite? Your criteria for the choice may differ—that’s OK, because one way or the other we’re talking about guys who helped our favorite team.

Let’s get into it.


Jason Varitek and Derek Lowe

This is kinda cheating since it’s two guys, but come on now: this feels like an easy one for me.

I expect that I’m going to see some of my OTM colleagues point out some of the other worthy contenders for this honor: your Nathan Eovaldis (Jalen Beeks, your contributions will never be forgotten), your Steve Pearces (even if you believe that WS MVP should’ve gone to David Price), your Jason Bays, etc. All worthy choices, to be fair!

But how are you gonna pick against a battery that was a huge part of a curse-breaking team in exchange for a reliever?

I was just a year old on July 31, 1997, when the Seattle Mariners agreed to send a lanky righty and a catcher out of Georgia Tech out to Boston in exchange for 1995 All-Star Healthcliff Slocumb. I couldn’t tell ya how good he was based off of an in-person experience. What I can tell you is that Slocumb had a very solid 1996 campaign with the Red Sox (168 ERA+ and 88 strikeouts across 83.1 innings), though his ‘97 numbers with our favorite club was….well, the 5.79 ERA in 46.2 innings tells you the story.

The Mariners had legit playoff aspirations in 1997, and any team in the hunt could almost always stand to bolster their bullpen. Boy, oh boy, are we lucky that Seattle fell into that box.

In return for Slocumb’s services, the Red Sox got a combined total of 43.6 bWAR, five All-Star selections, and one captaincy patch. The trade got us someone who threw and caught the same no-hitter in April of 2002, while it got Alex Rodriguez a swift knock to the head and the Oakland Athletics a quick “suck it” upon their elimination in the 2003 ALDS. Above all else, Varitek became a world champion twice over and Lowe won all three series-clinching games for the most important team in this franchise’s history.

It’s no question: this is the best haul we’ve ever gotten at or around the trade deadline.

— Fitzy Mo Peña


Hansel Robles

Toronto Blue Jays beat the Boston Red Sox 7-2
Steve Russell/Toronto Star via Getty Images

I have a soft spot for the 2021 team. I’ve written before about how I moved to Cambridge in September 2021 and spent nearly every night at Fenway Park from the day I moved until the end of the season. I was actually getting paid like a real adult, could walk to Fenway Park in about 25 minutes, and the team was winning against all odds.

Hansel Robles was brought in to bolster the bullpen at the deadline, and hurt more than he helped at first. In 13 appearances in August his ERA was over seven. In September he turned a corner. Over his final 14 appearances of the regular season, he didn’t allow a run. He secured two saves in the final series of the season, helping the Red Sox clinch a Wild Card spot. My friends and I used to joke that you could tell if you were getting good Hansel or bad Hansel based on the first pitch of the outing. In September 2021, bad Hansel never showed up.

Author’s Note: His playoff performance left something to be desired, but I was drinking for a lot of that. The whole run is kind of an adrenaline-fueled blur for me.

— Jacob Roy

Nathan Eovaldi

I’ve written about my gratitude and love for Eovaldi before. In only his second start for the Red Sox, he pitched a great game against the Yankees (back when we were both vying for the top of the division). For me, it was love at first sight. This game coincided with my wedding anniversary…as a newly single person. I was in the middle of a divorce that I didn’t ask for or want and watching Eovaldi come in and take down the Yankees felt like a personal victory. Fresh starts for everyone! That he later was so masterful over six innings—of relief, remember—in that incredible 18-inning World Series game against the Dodgers, even though he took the loss…gah! I still get choked up.

— Maura McGurk

Dave Roberts

World Series - Game 4: Red Sox v Cardinals
Photo by Brad Mangin/MLB Photos via Getty Images

Everyone wants to look at the 2004 trade deadline as the year Theo Epstein grabbed a first baseman that was so direly needed by a team that would end up winning the World Series for the first time in 86 years. Or, if it’s not that, it’s that the shortstop debate and the Nomar drama. That’s valid, sure, but Theo acquired a veteran player who had wheels on him and used him to do exactly what his profile suggested he was best at: stealing bases.

Funny enough, though he was used in 101 at-bats down the stretch, Roberts only stole 5 bases in the regular season, but everyone in the ballpark and in the world knew what he was there to do in the bottom of the ninth in that fateful ALCS Game 4. And he did exactly that. This team would not have won this game, let alone the World Series, if not for that stolen base. Full stop. Dave Roberts will possibly go to the Hall of Fame as a manager for the magnitude of success he has achieved as manager of the Dodgers, but his plaque will also say his only World Series as a player was as a member of the Boston Red Sox.

The other piece of this that made Roberts’ pickup so special was the player the Red Sox, or rather, the PawSox, sent to L.A., or rather, to the Triple-A Las Vegas 51’s. Henri Stanley never ended up playing a Major League game, but he was the perfect leadoff man in Triple-A. He hit .299 in 2004, was increasing his power as of that deal, and was on the speedier on the basepaths, though not enough to steal bases. This analytics aggregator article from earlier that season touts him as Johnny Damon Lite. I loved watching Stanley bat before some guys that would eventually make some marks on future Red Sox teams such as Kelly Shoppach, Cesar Crespo, former third base coach Carlos Febles, and a guy you may have heard of before, Kevin Youkilis. To go to McCoy in 2004 was a magical experience, and it was in part thanks to the magic of Henri Stanley.

A product of Clemson University, Stanley ended up a player agent, including to former Roberts-managed pitcher Yu Darvish. Roberts admits to Darvish inquiring about Stanley at least once when he pitched for the Dodgers in 2017. Unfortunately, Stanley never had so much as a cup of coffee in the bigs, which stinks because in today’s game, he absolutely would have a home at least SOMEWHERE with his career OPS in the minors topping .850. He was thrilling to watch, which made the deal for Roberts even more tantalizing to an 11-year-old kid who was about to see his team do the unthinkable against their rival, thanks to what would go down as his favorite trade deadline acquisition ever.

— Dean Roussel

Rick Aguilera

baseball player Rick Aguilera in Boston uniform, holding news Conference // The new Boston Red Sox closer Rick Aguilera met the media before Friday night’s (7-7-95) game at the Metrodome

The 1995 Red Sox probably shouldn’t have been as good as they were. I mean, seriously, what kind of baseball team relies on an unknown knuckleballer plucked off the waiver wire to be their ace? But, somehow, there they were, leading the American League East in July, as they had for most of the season. That’s when they traded for Minnesota Twins closer Rick Aguilera.

I had never heard of Rick Aguilera until a few weeks before he was traded to the Sox. But in those weeks he had become the most important baseball player in the world, the guy the Sox had to get if they were going to shore-up the pen for a pennant chase. And that, to me, is what can make the trade deadline so fun. Suddenly, otherwise unremarkable players are thrust into the spotlight and given the opportunity to become heroes to an entire fanbase who didn’t even their names at the start of the season.

Rick Aguilera, unlike the guy Dean wrote about, did not become a Red Sox hero. But he was nails down the stretch, saving 20 games and putting up an ERA+ of 184 before returning to the Twins the very next season. He was like some magical drifter who came and lived with us for a few months, taught us the meaning of life, and then slung his bindle over his shoulder one day and walked off into the sunset.

Aguilera would later call the trade the lowest moment of his career — he apparently really, really didn’t want to leave the Twins — and it was also an incredibly awkward trade, since he was traded in the middle of a Twins-Red Sox game and was immediately asked to record a save against guys who had been his teammates like five minutes before. But it was cool for us. So, thanks, Rick. Sorry you hated those three months in Boston so much.

Filed Under: Red Sox

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