Milliken: Should Craig Breslow get aggressive for Willson Contreras?

For years, Willson Contreras has been one of those names that has constantly surrounded different Red Sox trade speculation. Now, it seems like there’s a real chance he could end up calling Fenway Park home, with reports from Chris Cotillo of Masslive.com and Katie Woo of The Athletic confirming Craig Breslow’s "significant interest” in the first baseman. After choosing to not make an offer to Kyle Schwarber and failing to land Pete Alonso, Contreras has quickly become one of the more intriguing names that could end up filling the hole at first base in Boston, while also being a threat in the middle of the lineup.

Contreras is entering his age-34 season and is coming off a really solid year after moving to first base exclusively. He slashed .257/.344/.447/.791 with 20 homers and 31 doubles in 135 games, which was good for a 127 wRC+. Not quite at the levels of his injury-riddled 2024 campaign (141 wRC+ in 84 games), but it was nice to see him produce without freak injuries taking him off the field again. Over the last two seasons, his 130 wRC+ ranks 25th in the sport (minimum 800 PA). He also ranked 8th in xwOBA for first baseman in 2025, which had him ahead of names like Freddie Freeman, Vinnie Pasquantino, and Josh Naylor. Who ranked #1 in that stat you might ask? Alonso.

Since the start of the offseason, Brelow has emphasized the importance of adding more power to the lineup, which was a clear need after watching the Red Sox struggle to generate offense against the Yankees in the Wild Card round. Following the trade of Rafael Devers, the Red Sox ranked 23rd in homers, but were 9th before the deal. Contreras won’t bring the same power as Schwarber or Alonso, but he’s a safe bet to hit 20-30 homers, which would likely surpass the total reached by Red Sox first baseman in all 162 games last year (21). Even at age-33, he ranked in the 87th percentile for xwOBA, 85th percentile in xSLG, 86th percentile in Barrel%, and 76th percentile in Launch Angle Sweet-Spot%, with 95th percentile Bat Speed. While diving through his batted ball data, it was interesting to see his PullAIR% jump up to 19.8 in 2025, which should play quite well at Fenway Park if given the opportunity. His OPS on the road was .824 compared to .752 at home last season.

The one part of Contreras’ offensive game that isn’t great is his K%, which sat at 25.2 in 2025. It’s not like he’s hovering around 30%, but for a team that had the 10th-highest mark in the sport, it’s noteworthy. To be fair, it was a slight improvement over what Contreras posted in 2024 and he was able to improve his Whiff% considerably, jumping from the 2nd percentile to the 23rd percentile. I’d be curious as to whether there’s a way for him to get his BB% back to where it was in 2023 and 2024 as well, even with him still posting a solid 7.8 mark in 2025 after ranking in the 97th percentile a year ago. I also want to give Contreras his flowers for having a career .845 OPS with RISP, which is something this team badly needs after their inability to regularly cash-in last season.

On the defensive side of things, Contreras didn’t look overwhelmed in his first extended taste of first base. He was able to post 6 Outs Above Average, which was the 4th-best mark of anyone at the position in 2025. Only Ty France, Matt Olson, and Carlos Santana were better. It’d be interesting to see how the Red Sox would deploy him, especially since Cardinals manager Oli Marmol recently left the door open for him to get some work at catcher again. Splitting some time between first base, DH, and catcher could make a lot of sense, especially with Triston Casas still in the organization, Masataka Yoshida’s uncertain future, and Breslow continuing to discuss potential upgrades at catcher.

Another positive aspect to potentially adding Contreras is that his contract isn’t lengthy or overly inflated. After agreeing to a 5-year, $87.5 MM deal before the 2022 season, he’s only owed $18 MM in 2026 and $18.5 MM in 2027. There’s also a $17.5 MM team option for 2028, which includes a $5 MM buyout, but an AAV in the $18 MM range puts him in a similar camp as Yoshida from a financial standpoint. That should be something this front office is able to handle, whether their follow up move would be re-signing Alex Bregman or dealing for Ketel Marte. For all we know, the Cardinals might be willing to eat a chunk of money in order to get a better return, which just happened in the Sonny Gray deal.

According to Red Sox Payroll (follow them if you don’t, they do an incredible job), the Red Sox Luxury Tax number currently sits at $226.19 MM. Just combining the projected money for Bregman and Contreras in this situation ($40-$50 MM), it would be a tight fit, but there’s always the path of trading Jarren Duran, Patrick Sandoval, Yoshida, or even Brayan Bello in different deals to create some more financial flexibility. Just examining some of the other names they’ve been connected to (Eugenio Suarez, Kazuma Okamoto) and with Bregman still being reported as their #1 priority, they’d be working with a similar budget situation, so it’s more than plausible.

What will the return look like? That’s a good question. As I mentioned above, a lot of it will come down to how the money is handled in the deal. If a significant amount of money doesn’t get eaten, I’d expect a prospect in the 8-10 range to be going the other way. Who knows, maybe the package could get even more lucrative if someone like Jojo Romero is involved, who would help replace the loss of Justin Wilson (FA) and Steven Matz (Rays) in free agency. While the Red Sox have been connected to Brendan Donovan, they aren’t reported to be a front-runner, so I wouldn’t expect a bigger deal including him either. Could Jimmy Crooks be a target with how the Red Sox are pursuing some catching help? He’d be a great fit alongside Carlos Narvaez. As we know, Chaim Bloom knows the Red Sox farm system well and the two sides have had plenty of trade conversations in recent years. Who knows what could come to fruition…

Overall, I’d be happy with the Red Sox dealing for Contreras. It still leaves you plenty of room to play this game of chicken with Bregman or to go all-in on Marte. Who knows, maybe they even make a run at Kazuma Okamoto for third base. Beyond that, Contreras was very well-liked in the Cardinals clubhouse, so he should fit in well with the current group in Boston. You wouldn’t have to worry about posting a 96 wRC+ at the position again or being in the bottom 3 for Defensive Runs Saved. This would be a significant upgrade on both sides of the ball, even if he doesn’t pack the same punch at the plate as a guy like Alonso. Does that excuse their weak pursuit of the former Met? Nope. But this is about making the Red Sox better in 2026 and 2027, and Contreras should be able to do that.

Time to see if Craig Breslow and Chaim Bloom can make some more magic.