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Milliken: The meaning behind the Garrett Crochet extension? Urgency and Conviction.

Author Tyler Milliken

EXHALE! Since the moment Garrett Crochet was acquired by the Red Sox for a package of Kyle Teel, Braden Montgomery, Chase Meidroth, and Wikelman Gonzalez back in December, there’s been an internal battle most fans have been fighting. Was it safe to fall in love with one of the most electric young arms in the sport, especially as it looked like negotiations between him and the team weren’t particularly close for most of the spring? Thankfully, that question has been put to rest by Craig Breslow and John Henry after inking Garrett Crochet to a 6-year, $170 MM extension that starts in 2026 with no deferrals.

Urgency and Conviction. Those were the two words that immediately flooded my mind after taking a few minutes to process the nuke Jeff Passan dropped on the timeline. There was a clear understanding from the Red Sox of what was at stake if they decided to kick the can down the road on another key member of their nucleus.

It wasn’t hard to see Crochet’s price potentially doubling, especially if he takes the step forward many are expecting from him in 2025. At that point, it wouldn’t make much sense for Crochet to sign an extension with only a year until free agency, as he’d be the rare ace that could cash in before his age-28 season That would leave the front office in a nearly impossible spot of trying to justify the package they gave up for him, while also being forced into a massive bidding war and paying the full free agent price.

Keep in mind, while Crochet’s 3.58 ERA in his first season as a starter was good but not great, all the underlying metrics screamed to everyone that he was an ace. In terms of FIP, he finished 3rd in all of baseball with a 2.45 mark (minimum 145 IP), only trailing Tarik Skubal and Chris Sale, who both went on to win the Cy Young in their respective leagues. On top of that, he had the highest K% of any starting pitcher and was the hardest throwing southpaw starter in the game. That also included elite command with only a 2.0 BB/9. Not too shabby for a guy being forced to play for one of the worst teams in the history of sports.

This all pointed to whether the Red Sox had the conviction to be all-in on their player evaluations. From the moment the Red Sox acquired Crochet, they’ve screamed he’s an ace and top 5 pitcher in the sport, despite his resume not justifying yet. For an organization that hasn’t been able to develop an ace since Jon Lester, this was their chance to lock down a team-friendly deal for an arm of that caliber.

To Breslow’s credit, he showed the needed urgency to get the deal done now. He didn’t let Crochet’s camp push him around as they tried to set an Opening Day deadline for these talks. Instead, the organization seemed confident it was only a matter of time. Last week, Red Sox CEO and President Sam Kennedy was basically gloating about all the deals they’ve been able to get done over the years, despite arbitrary deadlines. This was Breslow’s only chance to secure a deal like this and once there was blood in the water, he didn’t stop. That became clear after Crochet revealed to Rob Bradford that extension talks were down to the wire before he made his Red Sox debut against the Rangers (5 IP, 2 ER/R, 4 K, 2 BB).

It’s been impressive to see Breslow continue to show he can convince ownership to spend, and whether that’s because of the help of Theo Epstein or not, it’s a great sign of what could be possible for the franchise in the coming years. Crochet’s $28.33 MM AAV shouldn’t be a burden or their books whatsoever, and if he turns into the #1 pitcher the Red Sox believe he can be, it will be one of the better contracts in baseball. Right now, that would rank as the 7th-highest AAV among starting pitchers (including Shohei Ohtani), but there’s a fair chance he drops even farther down that list with Dylan Cease, Zac Gallen, Framber Valdez, and Michael King on the verge of free agency.

Diving deeper into the details of the contract, Crochet does have an opt-out after the 2030 season. That would be following his age-31 season, which would make him a year older than when Max Fried reached free agency, who just signed the biggest deal for a left-handed pitcher in baseball history at 8 years, $218 MM. If Crochet pitches anywhere close to what he’s capable of, it’s hard not to imagine him jumping at that opportunity. In the year 2031, $28.3 MM AAV might be backend rotation money with the price of pitching continuing to go up.

While it was likely necessary for the Red Sox to include that type of opt-out for Crochet with where he’s at in his career, it was also huge to get some protection against a major injury. According to Alex Speier of the Boston Globe, the Red Sox secured a conditional option of $15 MM for 2032 if Crochet misses 120 consecutive days due to a significant arm injury. It’s very reminiscent of the clause John Lackey had in the 5-year, $82.5 MM deal he signed with the Red Sox back in 2009. Only difference is that Crochet’s number is much more expensive, since Lackey was making the league minimum in 2015 after getting flipped to the Cardinals for Allen Craig and Joe Kelly.

That type of detail would be significant in any massive contract for a pitcher, but it makes even more sense for Crochet, who has dealt with a lengthy list of injuries dating back to college. He’s already had one Tommy John procedure back in 2022, but as we’ve seen with Nate Eovaldi, Walker Buehler, and even Garrett Whitlock, that doesn’t mean an end to UCL’s barking. If the clause is forced to come into play, it would also void Crochet’s opt-out after the 2030 season, ensuring the Red Sox eventually get the production they’re paying for.

Crochet’s extension did set some new standards, with it being the most expensive deal for a pitcher between 4 and 5 years of service time. The previous record was the 5-year deal Jacob deGrom agreed to with the Mets in 2019 for $137.5 MM. Passan also noted that Crochet was the first pitcher ever to sign a deal for at least $100 million before throwing at least 800 innings in either MLB or the NPB. That type of risk is necessary for the Red Sox with their hesitancy to hand out long-term deals to players over the age of 30 or go the extra mile for someone like Fried, who convinced the Yankees to tack on an extra year to his deal over the offseason.

Next up for Crochet will be showing the Red Sox why they made the right decision to pay him. That starts tonight against the Orioles, as he’ll be tasked as the stopper for a club that has lost four in a row after an exhilarating win on Opening Day. Seems like a perfect time to give the fanbase a preview of what the rest of this decade should like with him at the top of the rotation.

Tyler Milliken started out at the Sports Hub as an intern in 2020 for the Zolak & Bertrand program before eventually becoming the associate producer in late 2021. He often joins the baseball conversation on Zolak & Bertrand and is a contributor to The Baseball Hour throughout the season. Along with that, he has been a co-host on DraftKings Name Redacted Podcast with Jared Carrabis for the last two years, where they cover everything going on with the Red Sox. Born and raised in Brockton, he reps the city proudly.

Milliken: How did the Red Sox end up in this spot with Rafael Devers…

What the hell has happened in the last 48 hours? It was hard to find better vibes than what the Red Sox had cooking at the end of last week, as Alex Bregman arrived in Fort Myers fresh off signing his 3-year, $120 MM deal with visible excitement about his new home. At that time, the message from the organization had been about making Bregman the club’s second baseman, but that changed quickly once Alex Cora wouldn’t commit to a defensive position at Bregman’s introductory presser.

“We’ll talk about that later on,” Cora told the media. “Right now, there’s a lot of stuff going on as far as where we’re going to be roster-wise. We’ll make the decision when we have to make it… He hasn’t played second base in the big leagues. I do believe he can be a Gold Glove second baseman, too. There’s other stuff that comes into play as far as roster construction and what’s better for the team and what can be the best lineup. Competition comes into play.”

If you want to go back to the first initial buzz between the Red Sox and Bregman, it started with Cora gushing about viewing Bregman as a second baseman at the Winter Meetings. He doubled down on that sentiment roughly a month later at Fenway Fest. “Raffy Devers is our third baseman. Alex was a Gold Glover at third base and we all know that, but in 2017 I had a conversation with him, and he needed to play third because it was Correa and Altuve. I always envisioned Alex as a Gold Glover second baseman. His size, the way he moves.”

That message from the Red Sox never changed once as they pursued Bregman. Jeff Passan reported within the hour of the agreement going public that the plan was for Bregman to be at second base. Not to mention, Breslow had emphasized at the end of season presser and again at the Winter Meetings that they hadn’t discussed moving Devers off of third base, despite there already being rumors about their interest in Nolan Arenado.

  • Whenever the question about a potential positional change for Devers came up, Breslow made it clear that those talks would happen internally before anything else. “Any conversation that we would have about [a position change] is going to happen internally before it goes external. At the same time, we saw progress [from Devers] on the defensive side, and it’s unclear to what extent the knees and the shoulders impacted his ability to defend at third [down the stretch]. But what we’re after is putting a winning team on the field. And we’ll have conversations as needed, as things go, but as of right now, that’s not where we are.”

    From Devers’ standpoint, I don’t think it’s hard to see why he’s upset about the Red Sox dropping a positional change on him. He was never spoken to about moving off of third base all offseason, despite his bosses saying they’d talk things over with him if something changed. Instead, he heard exactly what the fans were told, which was that Devers was the third baseman and Bregman could win a Gold Glove at second.

    As we know, the Red Sox weren’t seriously in on any of the DH/OF options like Teoscar Hernandez and Tyler O’Neill. In Jen McCaffrey’s story about how the Bregman deal went down, it was noted that after the Red Sox missed out on Juan Soto, they turned their focus to Bregman. Even Sean McAdam had written in November that Arenado was essentially a “Plan B” for the Red Sox, which was obviously the case as they waited out the Bregman sweepstakes over the last two months.

    During that entire period, the Red Sox had the opportunity to at least approach the topic with Devers. That would’ve ensured they kept their word from earlier in the offseason, while also showing a level of respect towards Devers, who was reportedly promised he’d be the third baseman of the team for “several” years after signing his extension. Yet the organization dropped the bomb on him this past Friday after Bregman had already been signed and he had been in Fort Myers since the middle of January. 

    Christopher Smith on X (formerly Twitter): "Cora and chief baseball officer Craig Breslow met with Devers Friday to discuss different scenarios, including the possibility of him being the DH.Cora said Devers told him and Breslow "I'm a third baseman.""I knew he was going to say that," Cora said. "So I wasn't surprised" / X"

    Cora and chief baseball officer Craig Breslow met with Devers Friday to discuss different scenarios, including the possibility of him being the DH.Cora said Devers told him and Breslow "I'm a third baseman.""I knew he was going to say that," Cora said. "So I wasn't surprised"

  • While many didn’t take Devers’ agent, Nelson Montes de Oca, too seriously over the course of the offseason, he made it clear that his client expected to be at third base. Whenever rumors started to fly about Bregman or Arenado, Devers’ camp sent their message both locally and nationally. You even had, which pointed to him feeling disrespected by those saying he should be a DH moving forward. Beyond the poor communication, this is an example of just not reading or understanding your players correctly, which is a dangerous game to play with someone who just signed an 11-year, $331 MM extension.

    If the front office felt it was that important to upgrade the infield defense, that should’ve been communicated at the start of the offseason. Strictly from a baseball perspective, Devers wouldn’t have much of an argument, but they chose to muddy the waters with their comments about his improved performance in 2024 and Bregman playing second base. Devers himself admitted that he thought he made strides last season, which only matches what the organization said about him.

    I was shocked when the Red Sox applauded Devers’ defense at the time. While he didn’t fall into his typical error funks for once, he registered a rough -6 Outs Above Average and -9 Defensive Runs Saved. So, why not be upfront when the data in front of you justifies the conversation you need to have with your best player? If you were that committed to Devers only swinging a bat moving forward, the best course of action would’ve been to let him process it away from everything. Even after coming up short on that front, they could’ve slow played the conversation early in camp to make up for the lack of communication in the first place. Nobody is a bigger Kristian Campbell fan than me, but why ruffle any feathers until he proves to be a real candidate for the Opening Day roster?

    Fuzzy on X (formerly Twitter): "Red Sox mega prospect Krisitian Campbell last year:.330-BA/32-2B/20-HR/24-SB/.440-OBPHe was seen today taking reps at 2nd base, while Bregman was at 3rd base. Again, give me chaos pic.twitter.com/vTpiK1sowQ / X"

    Red Sox mega prospect Krisitian Campbell last year:.330-BA/32-2B/20-HR/24-SB/.440-OBPHe was seen today taking reps at 2nd base, while Bregman was at 3rd base. Again, give me chaos pic.twitter.com/vTpiK1sowQ

  • Make it appear as if Campbell was battling for a spot in left field. In that scenario, Jarren Duran could move to center field where he posted elite defensive numbers in 2024 and Ceddanne Rafaela works in a super-utility role. If Campbell decided to show out and Rafaela was deserving of an everyday role in center field, then the convo changes during camp and there’s direct proof of why that’s happening.

    It wasn’t only Devers that was put in a tough spot with how the Red Sox framed things either. They made it pretty hard to envision where Masataka Yoshida would slot into things. That’s a major reason why I was cautious to pencil in Devers at DH and Bregman at 3B because if you hope for Yoshida to rebuild any of his value, that’s not happening with a lot of time on the bench. This was a way to put your best offensive lineup out there, keep everyone happy, and still improve your defense from where it was a year ago.

    Does the poor communication from the Red Sox justify Devers completely shutting down the idea of being a DH or first baseman? No, not one bit. In a perfect world, you’d hope his sole focus was on the Red Sox being the best version of themselves, but he said himself that he feels like a victim of bad business. This is where Cora will have a chance to earn his money as a player’s manager, but it’s going to take some real work after contradicting himself the last few months.

    NESN on X (formerly Twitter): "Alex Cora shuts down the notion of any tension between Devers/Bregman:"It didn't look [awkward] at the house, I'll tell you. They were talking for 45 minutes. Things like this happen."#RedSox pic.twitter.com/VvVFenx0CB / X"

    Alex Cora shuts down the notion of any tension between Devers/Bregman:"It didn't look [awkward] at the house, I'll tell you. They were talking for 45 minutes. Things like this happen."#RedSox pic.twitter.com/VvVFenx0CB

    The Red Sox can claim that Campbell forced them to reconsider their defensive alignment, but he hasn’t done anything to dramatically change their evaluation since the offseason started. If you felt this strongly about him playing against the Rangers on March 27th, why not approach things with that outlook all offseason? Talking out of both sides of your mouth did you no favors in this scenario and has now created an uncomfortable position for a team looking to solidify themselves as contenders in the American League.

    Over the next 5 weeks, there’s going to be a focus on Red Sox spring training that hasn’t existed in a long time. Every defensive rep that Bregman and Devers takes is going to be questioned or noted. Same goes for Campbell, who will be in the midst of his first big league spring training. Even when it comes to the media, players are going to be asked about it constantly, which is where you risk guys stepping in it and starting fires (Yes, I’m talking about Triston Casas). That attention is a product of how the Red Sox handled things over the course of the offseason and into camp, which they can only blame themselves for.

    At the end of the day, it’s Cora’s job to fill out the lineup. If he wants Devers at DH, that will be a pill he’s forced to swallow. It just feels like there was a simpler way to handle this situation that didn’t make Devers feel blindsided and defensive. The last thing the Red Sox need with their image on the upswing again is a public dispute with their longest-tenured player, who is right at the center of what should be a lengthy competitive window for the organization.

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