Mark your calendars. It’s November 5th and the Red Sox have already sent their fanbase into a frenzy with their first move of the offseason. On Monday night, Craig Breslow and company made the surprising decision to extend the Qualifying Offer to Nick Pivetta, which comes with a price tag of $21.05 MM for 2025.

That’s a somewhat steep price for Pivetta, who’s shown flashes of being more than a backend starter, but has never been able to capture that for a full season in his big league career. It’s a calculated risk from Breslow, who has a chance to earn a compensation pick if Pivetta chooses to decline the QO and sign elsewhere, which would result in a draft pick after the second round. Just for reference, Roman Anthony and Kristian Campbell are two recent compensation picks over the last few years.

Current projections for Pivetta on the free agent market had him landing a 3-year deal in the range of $45-48 MM, with Kiley McDaniel having the most bold projection of 3 years, $63 MM. While the QO is a clear overpay for Pivetta’s services, I wouldn’t have an issue with the decision if the Red Sox forgoed staying under the first luxury tax threshold of $241 MM. At that point, if you’re not counting pennies and willing to spend, I have no problem overextending to ensure you’re going to have some of the better pitching depth in the sport.

You could picture a reality where Kutter Crawford is moved to the bullpen in a high-leverage role to help with the losses of Chris Martin and Kenley Jansen. If there’s ever an injury or issue, you have Crawford ready to step-in and if Pivetta can’t get the job done, he’s had his own success in a bullpen role while in Boston. This would all be with the belief that the front office found a way to add a top of the rotation arm, which is the team’s most obvious need as they prepare to make a push to win the AL East.

• What’s the problem with that dream? I don’t have much faith in the Red Sox pushing past that $241 MM mark, which is a shame if they’re actually serious about their competitive window opening up. My guess is they’re still at least a year away from that point as they wait on the arrival of The Big 4. I expect the plan is to get close to that threshold number by the end of 2025, which is an improvement over the last two seasons, but still a reminder that the team isn’t ready to go all in.

  Truth is, it’s extremely early in the offseason. Similar arms like Luis Severino and Nick Martinez were offered the QO, so this isn’t some absolutely insane decision by the front office. But it has a chance to blow up in their face if they enter another season with clear issues on the big league roster while being under the luxury tax.

  When examining where the Red Sox will be if Pivetta accepts the QO, that would put their luxury tax number at roughly $196 MM (@RedSoxpayroll). That leaves about $45 MM to work with as they try to fulfill their offseason needs, which include a top of the rotation arm, an impact right-handed bat, high-leverage bullpen help, and a backup catcher. Immediately your mind starts to float to the trade market in this scenario, where you start to wonder if someone like Crawford or Tanner Houck could be moved in a bigger deal for someone like Garrett Crochet of the White Sox.

  We know the Red Sox were checking in on Crochet at the trade deadline this past year, so he’s clearly on their radar. If the Red Sox are searching for a young arm with ace potential, they’ll have some flexibility with Pivetta as part of the mix to deal from that group. Still, it potentially points to the Red Sox not flexing that financial muscle many have been waiting on with Corbin Burnes, Max Fried, and Blake Snell all on the free agent market.

  Tyler Milliken ⚾️ on X (formerly Twitter): "Here's @jonmorosi on Nick Pivetta's market being "surprisingly strong" at the GM Meetings. If you go back to the trade deadline, the Astros were hot on Pivetta before dealing for Yusei Kikuchi.pic.twitter.com/UigXPZbkvn / X"

  Here's @jonmorosi on Nick Pivetta's market being "surprisingly strong" at the GM Meetings. If you go back to the trade deadline, the Astros were hot on Pivetta before dealing for Yusei Kikuchi.pic.twitter.com/UigXPZbkvn

• Are the Red Sox finally on the right path with their rotation depth?

  Over the last 3 seasons, whenever Red Sox officials are asked about why the team has fallen off in the second half, it revolves around pitching depth. That’s arguably the main reason Breslow was hired as Chief Baseball Officer roughly a year ago with the organization starving for a pitching pipeline to finally be constructed again. Heading into 2025, it’s clear there’s a stable of arms awaiting at Triple-A and Double-A that hasn’t existed for quite some time.

  If the Red Sox properly address their need at the top of the starting rotation for 2025, it should look like [INSERT], Tanner Houck, Lucas Giolito, Brayan Bello, and Crawford/Pivetta. It’s hard to forecast exactly how things will play out, but I’d expect at least one name of the group above to not be here on Opening Day (Houck, Crawford, Pivetta). For all we know, Pivetta might reject the QO and Breslow ends up looking like a genius for reading the market correctly, which seems possible with a “surprisingly strong” market already shaping for the righty at the GM Meetings.

  That would leave both Richard Fitts and Quinn Priester starting the season at Triple-A, with both showing at the end of 2024 they were capable of making competent spot starts if called upon. Beyond those two, Cooper Criswell, Zach Penrod, and Hunter Dobbins are also options, with Wikelman Gonzalez likely due for a promotion to Worcester.

  The Criswell situation is a little different than the other names mentioned above because he’s out of options, but there’s no reason he can’t be in the big league bullpen serving a role similar to Chase Anderson. Not to mention, you can actually use Criswell in spots that have some leverage to them. It’s easy to overlook that he posted a 4.08 ERA/4.15 FIP in just under 100 innings in his first season working with Andrew Bailey.

  It’s a shame that Luis Perales ended up blowing out his elbow last summer, because he would’ve taken the group at Triple-A to another level. He was Baseball America’s #57 ranked prospect before needing to get his UCL repaired. Still, there are arms like David Sandlin and Connolly Early who could easily be pushing for a promotion to Triple-A after the first few months of 2025.

  Tyler Milliken ⚾️ on X (formerly Twitter): "Richard Fitts picks up the first strikeout of his career.Tanner Houck asks for the ball.Through 2 scoreless. pic.twitter.com/jGWLHOVcTc / X"

  Richard Fitts picks up the first strikeout of his career.Tanner Houck asks for the ball.Through 2 scoreless. pic.twitter.com/jGWLHOVcTc

• Just going back to the depth of the Triple-A rotation over the last four seasons shows how dire things were on the pitching front. After Criswell and Fitts (who hadn’t pitched at AAA), Grant Gambrell, Brian Van Belle, and Jason Alexander were the next guys up. It was clear the front office had no faith in those guys either, as they added Naoyuki Uwasawa and Brad Keller, while continuing to jerk Winckowski between the rotation and bullpen.

  Things were supposed to be better in 2023 with 7 rotation options between Chris Sale, Corey Kluber, Tanner Houck, Crawford, Pivetta, Whitlock, and James Paxton, but injuries derailed that group. It also didn’t help that Pivetta and Kluber were basically black holes in terms of production. Before you knew it, Matt Dermody was starting for the Red Sox in June, who was a walking public relations disaster that the organization embarrassingly had to rely on.

  In 2022, Darwinzon Hernandez, Thomas Pannone, Connor Seabold, Josh Winckowski, and Brian Keller were waiting in the wings. Yes, Garrett Whitlock and Crawford were options in the big league bullpen, but they were initially slated to strengthen a thin group late in games. This ultimately led to the entire pitching staff collapsing after both were forced into the rotation and there was nobody able to offer the proper support in the minors.

  Just looking at the Dodgers this season, it’s hard to ignore what their pitching staff has overcome. They’ve had an entire rotation of arms go down and yet they just won the World Series. Tyler Glasnow, Clayton Kershaw, Dustin May, River Ryan, Gavin Stone, Tony Gonsolin, and Emmet Sheehan were on the IL, with Jack Flaherty, Yoshinobu Yamamoto, and Walker Buehler forced to carry the load.

  Now, there’s an obvious difference between the elite talent the Dodgers have at their disposal, but they burned through a ton of depth and STILL made a significant acquisition at the deadline. They leaned on Ryan, Knack, Justin Wrobleski, and Ben Casparius (Game 4 of the World Series) at different points to survive the year. Guys like Bobby Miller, James Paxton, and Buehler were shells of themselves, but racked up a combined 47 starts.

  MLB Metrics on X (formerly Twitter): "The Dodgers were able to win the World Series with essentially an entire starting rotation sitting on the IL. Just unbelievable. pic.twitter.com/T40NV4O1Jq / X"

  The Dodgers were able to win the World Series with essentially an entire starting rotation sitting on the IL. Just unbelievable. pic.twitter.com/T40NV4O1Jq

• It goes to show what a big market organization can do when they not only flex their financial muscle but also build up a farm system of quality arms to lean on. Part of the equation for building this depth also factors in the pitching at your disposal. The Dodgers knew the injury concerns that could follow with Glasnow and Kershaw’s history, Yamamoto making the transition from Japan, Gonsolin recovering from Tommy John, Maye being a question mark after getting his flexor tendon repaired, and Buehler’s lengthy recovery from a second UCL repair.

  Fortunately, the Red Sox rotation doesn’t have that many injury questions at the moment. So, they shouldn’t need such a lengthy list of arms unless the injury bug shows up and beats the brakes off of everyone. But the Dodgers should be the ultimate reminder in 2025 of how crucial building that depth is, even if you feel like you’re making progress in that department.

  Criswell, Fitts, and Priester as starting options are a decent place to start though. I’m guessing the Red Sox would also factor Whitlock and Winckowski into that conversation, but I’d hesitate, especially until the bullpen picture is a bit more clear. Dobbins feels like the most underrated arm of the group, with his combination of velocity and 4 secondaries.

  The goal should be to continue to find more useful depth arms like Criswell on both the free agent market and through trade. Especially until the pitching pipeline reaches the level an organization like the Dodgers is at. It’s possible to do that and add elite talent… the two shouldn’t be separated.

  Still just a year later, it’s much easier to see the pitching vision. 3 homegrown starters in the rotation that made 30 starts in 2024. Then 3 to 4 arms in the wings that profile as backend rotation options, with other intriguing guys like Yordanny Monegro and Blake Wehunt not too far off.

  Next up, go give the bag to a top of the rotation arm and the whole picture looks a lot better. Better yet, go over the luxury tax and ensure you have a stable of arms that can go head to head with almost every team. The opportunity is right in front you.

  Tyler Milliken ⚾️ on X (formerly Twitter): "Hunter Dobbins is quickly becoming of the most interesting arms in the Red Sox system.Since his promotion to AA:3 Starts (16 IP)2.81 ERA/3.00 FIP10.7 K/93.4 BB/92.86 ERA over 10 starts this season. Nice to see a crop of arms emerging in the system.pic.twitter.com/ly77LK66CU / X"

  Hunter Dobbins is quickly becoming of the most interesting arms in the Red Sox system.Since his promotion to AA:3 Starts (16 IP)2.81 ERA/3.00 FIP10.7 K/93.4 BB/92.86 ERA over 10 starts this season. Nice to see a crop of arms emerging in the system.pic.twitter.com/ly77LK66CU

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