Red Sox trade deadline primer: 3 early storylines to watch (2024)

With the trade deadline approaching in less than 50 days, it’s crunchtime for many teams.

The Boston Red Sox sit at 33-34 after a 4-1 loss to the Philadelphia Phillies on Tuesday.

The last two Red Sox trade deadlines have lacked a clear direction, and it has resulted in two straight last-place finishes. This summer marks the first trade deadline for new chief baseball officer Craig Breslow, and because of that, it will be an important time for him to shape the future of the club.

With that in mind, over the weekend, the Financial Times published an extensive profile on Red Sox principal owner John Henry, who made some interesting comments about the team’s payroll and how it correlates to winning.

“Because fans expect championships almost annually, they easily become frustrated and are not going to buy into what the odds actually are: 1-in-20 or 1-in-30,” Henry told the newspaper.

Henry was also frustrated by the response to chairman Tom Werner’s remarks this past offseason about the team needing to go “full throttle” to improve for 2024, noting that those remarks “overshadowed every other word, paragraph and interview of the winter because it reaches so deeply into the false belief that many fans and media have that you should mortgage the future each year for the present.”

Despite speculation, Henry also noted the Red Sox would not be put up for sale, saying they “generally don’t sell assets.”

The comments made it seem even more apparent that the Red Sox are continuing to lean into their sustainable approach: building for the future.

Tuesday, manager Alex Cora was asked for his opinion on Henry’s comments.

“I like John. I respect John. He’s invested. That’s what I can tell you. We had conversations throughout the year, throughout the offseason about where we are at, what we’re trying to accomplish and where are we going. And he wants to win. He wants to win,” Cora said. “Obviously, he said what he said and people are going to feel differently about what he said — or agree with him. From my end, I think we are in this situation as an organization, probably better than last year.

“Our young players are doing an outstanding job. Some veterans are stepping up, the pitching program is better. I think, record-wise, we’re the same as last year. But as far as the process and where we are structure-wise, we’ve taken a step forward. That’s what he wanted.”

On one hand, the Red Sox are a .500 team struggling for consistency in a tough division. On the other, they’re a young team that’s sustained a .500 record despite a slew of injuries to key players. If they can regain health and make a push in July, adding for a wild-card push might be more realistic. But is that the message Cora is getting from Henry and upper management?

“Nobody in the clubhouse, the dugout or as a manager will say that they want the team to sell, but I understand where we are at as an organization, and we just got to keep playing better. We have to play better,” Cora said. “And whatever decision is made is going to be the decision that is going to be made. We’re going to respect it, and we’re going to keep going. I think Craig has a pretty good idea of who we are and what we can be in the upcoming weeks, but at the end of the day, that scoreboard, that standings is going to dictate what we’re going to do later on.”

The Red Sox can take three approaches to the trade deadline over the next several weeks, so we’ll take a look at how each might pan out.

If they buy: Adding pitching or a bat by trading prospects

Monday, The Athletic’s Jim Bowden compiled some trade deadline tidbits he’d been hearing and noted Breslow is searching for more starting pitching and a short-term solution at shortstop.

The Red Sox have been platooning David Hamilton and Ceddanne Rafaela at short, with Hamilton taking on more of the reps recently after a rocky start. Trevor Story is out for the year after shoulder surgery, but the Red Sox also have top shortstop prospect Marcelo Mayer closing in on the majors, so there’s an emphasis on a “short-term” solution there. The Hamilton-Rafaela combo has filled in well, though, and finding an impactful middle-infield bat isn’t an easy proposition, so there might be more of a focus on pitching. The caveat there, though, is that Bowden also noted how expensive and competitive the pitching market figures to be.

Boston’s top three prospects — Mayer, center fielder Roman Anthony and catcher Kyle Teel (all currently in Double A) — are almost certainly not on the trading block, and it might be hard to get any meaningful pitching additions without including one of them. Still, Boston’s farm system has taken a step forward over the past two years and could produce a few intriguing packages. Infielder/outfielders Nick Yorke and Matthew Lugo were just promoted to Triple A, and utilityman Chase Meidroth and first baseman Niko Kavadas could be intriguing pieces who could be packaged with one of the big leaguers in the following section. But are a few top-30 prospects and a big leaguer enough to nab a middle-of-the-rotation arm in this market?

If they sell: Impending free agents Tyler O’Neill, Nick Pivetta and Rob Refsnyder

The Red Sox have young outfield depth with Wilyer Abreu, Jarren Duran and Rafaela (not to mention Anthony on the horizon) in addition to O’Neill and Refsnyder. Losing the offense and leadership of O’Neill and Refsnyder would be a clear sign of a sell-off.

Meanwhile, outside of Tanner Houck, Nick Pivetta has been the most consistent Red Sox pitcher, and trading him would be a blow to the rotation. Given the high premium for pitching this summer, though, the Red Sox might be tempted to trade Pivetta, considering he’ll be a free agent this winter. Pivetta might not garner a prospect haul like some of the other rental starters, but if the Red Sox are out of contention, they’ll surely be listening.

If they buy and sell: Trading Kenley Jansen and/or Chris Martin

It might seem like trading Jansen or Martin would be a strict sell move, but not quite. Jansen is one of the top closers in the game, and for a contending team, he would be a commodity, and Martin is an established setup man. Meanwhile, the Red Sox bullpen has been strong with the ninth-best ERA in the league (3.54), and they also have a closer in the waiting.

Back in February, the Red Sox signed Liam Hendriks to a two-year deal as he recovered from Tommy John surgery. Hendriks set a return date of the trade deadline and is drawing close to that goal. He has been throwing all of his pitches on flat ground, and after a scheduled de-load week last week, he has started to ramp back up. He’ll likely start throwing off a mound within the next few weeks, with a rehab assignment in mid-July a real possibility.

With that in mind, it becomes easier to trade Jansen even if the team is still in the wild-card mix. Additionally, Justin Slaten (2.84 ERA) or Greg Weissert (2.93 ERA) could be options for the ninth, or even Brennan Bernardino (1.03 ERA). The club has bullpen depth with Zack Kelly, and in Triple-A, Isaiah Campbell and Josh Winckowski remain options.

(Top photo of Craig Breslow: Charles Krupa / Associated Press)

Jen McCaffrey is a staff writer for The Athletic covering the Boston Red Sox. Prior to joining The Athletic, the Syracuse graduate spent four years as a Red Sox reporter for MassLive.com and three years as a sports reporter for the Cape Cod Times. Follow Jen on Twitter @jcmccaffrey