The MLB Winter Meetings are in the rearview mirror, and while it took a couple of days, the Red Sox wound up coming home with one of the big prizes of the week in ex-White Sox ace Garrett Crochet. How does the club look now? And what moves do they still have to make?

The Herald’s Red Sox beat writers, Gabrielle Starr and Mac Cerullo, discuss.

Starr: Well, the Winter Meetings are over and the Red Sox certainly had a very interesting week. From losing out on Juan Soto Sunday and Max Fried on Tuesday, to making an enormous trade for Garrett Crochet right at the end of the meetings, they really had us in the first half, didn’t they, Mac?

Cerullo: Man, talk about a vibes shift. On Wednesday morning my Twitter feed was a complete mess, but the Crochet trade changed everything. Finally, after weeks, months and even years of talking a big game, the Red Sox went out and made the kind of big splash fans have been craving. Crochet has obviously been talked about as one of the big prizes of the trade market since last summer, but now that he’s officially Boston-bound, what do you think of the acquisition and the price the Red Sox paid to get him?

GS: This is the biggest pitching trade they’ve swung since Chris Sale, ironically enough. A December trade of four top prospects for a Chicago White Sox left-hander with two years of control left? The parallels are eerie! Going by past precedent, two Octobers from now Crochet will be on the mound closing out the ninth inning of the deciding game of the World Series!

Nevertheless, this was the kind of big move the Red Sox needed to make. It was time – arguably overdue – and they knew it. It’s evident in the return package they sent to Chicago, including their most recent first-round picks, catcher Kyle Teel and outfielder Braden Montgomery. Teel, especially, because he was supposed to be the catcher of the future. We know that prospects don’t always pan out, but it’s noteworthy that the Red Sox were willing to part with someone they previously felt was too important to trade. Not to mention the lack of catching talent in the upper levels of their farm system. What do you think?

MC: I think the club deserves a lot of credit for being willing to make the kind of investment needed to land an arm of Crochet’s caliber. Teel and Montgomery are significant pieces to lose, but like you said, prospects don’t always pan out, and the fact the Red Sox were able to get Crochet without giving up Roman Anthony, Kristian Campbell, or any of their current major leaguers is a big deal. They can figure out their catching situation later.

The thing with Crochet though is the prospects were only an upfront cost. If the Red Sox really want to make the most of that investment, they’ll need to sign him to a long-term contract extension. That won’t be cheap. He’s only 25 and should have the best years of his career ahead of him. Unlike with Max Fried, who will be 31 come Opening Day next year, an eight-year deal would be completely justifiable and only take Crochet through his age 33 season. I guess the question there is risk versus reward. Crochet might want the security of a life-changing contract, but he could also bet on himself, have a monster 2025 and raise his asking price significantly next offseason. The Red Sox could also try to lock him in at a more favorable rate now and risk him getting hurt or taking a step back, or they could wait and risk paying through the nose later. I’m honestly not sure which approach is better and it’ll probably depend in large part on what Crochet wants to do.

GS: Crochet is a very exciting addition to the rotation, though he’s not nearly as established as Sale. The Red Sox haven’t spent very much on pitching in the last half-decade, particularly young pitching, so let’s make a somewhat-flawed comparison to Brayan Bello, who’s a month older. Bello signed a six-year, $55 million extension through 2029 (with a club option for 2030) last March, when he was about to turn 25 and only had a year and a half of big-league experience under his belt. At the time, he’d thrown 214⅓ big-league innings over 41 games, 39 of them starts. Crochet is coming to Boston with 219 career innings, but this was his first season in the starting rotation; he’s pitched in 104 career games, but only made 32 starts.

The key difference, of course, is that Bello’s deal primarily covers his remaining years of club control; he was due to reach free agency after the ‘28 season. Crochet is only two years away from free agency. It’s always expensive paying for a player’s prime years, especially when he’s a lefty, but Crochet’s lack of a track record as a starter should help offset some of the cost. Any deal the Sox would offer would include a lot of performance-based incentives and escalators.

Another arm coming?

GS: It’s safe to assume the Red Sox have more pressing matters. They’ve been in several other trade rumors, specifically concerning the Seattle Mariners. What are you hearing?

MC: Well, Wednesday night MLB Network’s Jon Morosi reported that the Red Sox were working to acquire one of the Mariners’ starting pitchers, and local reporters in Seattle have specifically floated Luis Castillo as a possible target. There seems to be conflicting information on who the Red Sox would send in return, but two of the logical headliners would be Triston Casas or Wilyer Abreu.

Personally, I don’t want the Red Sox to trade Casas. He has 40-homer potential and is coming off an injury-plagued season, so the team wouldn’t be maximizing his value if they tried to move him now. There also aren’t as many internal alternatives at first base, and while I don’t think they necessarily need to trade Abreu either, there are other options in the outfield who could step in right away. Plus, he’s coming off a Gold Glove season and a sixth-place finish in the AL Rookie of the Year vote, so his value might be near its peak. I’m curious though, if Boston did make another trade for a starter, who would you prefer to see? One of Seattle’s arms? Someone else?

GS: You’re right, who plays first base if they trade Casas? Alex Cora has been very high on Abreu since they acquired him at the ‘23 trade deadline, but he’s certainly a valuable trade chip. The Mariners really need position players and bat power, but they’re holding tight to their starting pitching, and the Red Sox just gave up a ton of prospects for Crochet. And honestly, with the rotation now being Crochet, Bello, Tanner Houck, Kutter Crawford, and Lucas Giolito, with depth options of Richard Fitts, Quinn Priester, Cooper Criswell, and Josh Winckowski, is there really a need for another pitching trade? It may not be the most elite array of starting options, but they’re certainly not lacking in quantity.

What’s next?

GS: Let’s talk about free agency before we wrap this up. The Red Sox have barely spent on the market. What do you think they need, and who do you think they could get?

MC: Their top priority in free agency now should be finding a right-handed bat. Personally, I’d try to go out and get one of Teoscar Hernandez or Alex Bregman, if not both.

Hernandez’s appeal is obvious. He’s a right-handed masher who could slot right into Tyler O’Neill’s old left field role. He’s coming off a career year, helped lead the Dodgers to a World Series championship and has expressed interest in playing at Fenway Park. He checks every box.

As for Bregman, here’s a guy who also bats right-handed, produces at a high level and has 99 playoff games and two World Series rings to his name. He’d be an upgrade on offense, defense and in the clubhouse, and he’s also close with Cora, who served as Houston’s bench coach in 2017 before coming to Boston. If Bregman is open to playing second base I think he’d be a great addition, and if the club eventually decides to move Rafael Devers off third down the road, Bregman could slot back over to the hot corner. How does that sound to you?

GS: It would be a full-circle moment, since the Red Sox originally drafted Bregman in the 29th round back in 2012, but he didn’t sign. I’m not sold, though. He turns 31 the week of Opening Day, and I’m concerned by some of his recent numbers. His strikeout rate has climbed the last few years, and after walking at a 13.8% clip between 2018-23, he only walked 6.9% of the time this year. He entered the season with a .373 career on-base percentage, then posted a .315, his worst mark since his rookie year (.313).

Hernandez is a year older, but his bat offers more power. That’s what the Red Sox need most now that O’Neill is an Oriole. He’s coming off an All-Star, Silver Slugger, World Series championship season. Both players have hit very well at Fenway in their careers, though; Bregman averaged .375 with a 1.240 OPS in 21 games in Boston, and Hernandez has hit .282 with a .950 OPS.

One thing is certain, the Red Sox are far from done working on the roster. It’s going to be a very exciting few months!