2021-2022 Offseason Preview: The starting pitching market

With option decisions having been made and the five-day window after the World Series closed, we are now officially in free agency and player movement should be upon us. (The CBA situation is likely to slow down that progress, but players can change teams now.) For the coming week, every day we will look at a new position group of free agents and trade candidates, finding some who may or may not be fits for the Boston Red Sox this winter. Note that this is not a complete list of free agents and trade targets. Today we look at the starting pitchers available.

Where the Red Sox stand now

It’s not really up for debate whether or not the Red Sox need starting pitching help, but reasonable minds can disagree about how many new starters the Red Sox need and what quality of arm they should be targeting. So it’s useful looking at what they already have. At the top of the rotation is Nathan Eovaldi, who should get a handful of Cy Young votes for this season, and Chris Sale, who obviously has been a legitimate ace in the past and showed some real flashes towards the end of the postseason run. And then there’s Nick Pivetta, who is a back-end arm with consistency issues but someone who will likely be pencilled in for one of the top five spots to start next season.

After that, there are the big wildcards in Tanner Houck and Garrett Whitlock, both of whom have looked very good in relief but are likely to go into next season with starting pitching on the mind. One of the big questions for the Red Sox this winter is which one, if either, can be part of the top five on the depth chart. If Boston is willing to have one of them in that mix, then they really only need one clear top three starting pitcher, with another depth arm mixed in.

What’s more likely in my mind is that they grab two pitchers who they can see as clear top-five options, with Houck and Whitlock serving (not necessarily in this order) as the sixth and seventh options to fill in in case of injury. In that scenario, they could look for someone to slot in as a clear top three option in the same tier as Eovaldi and Sale, and then another whose talent is a bit below that but perhaps a bit above Pivetta. Either way, Boston certainly needs one good starter to come into the fold this winter, and more likely two.

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Free Agents

2021 stats and team(s) in parentheses.

This is not a comprehensive list, but rather some hand-picked interesting names. A full list can be found here.

• Max Scherzer (WAS/LAD; 30 GS, 179.1 IP, 2.46 ERA, 2.97 FIP, 5.4 fWAR)
• Carlos Rodón (CHW; 24 GS, 132.2 IP, 2.37 ERA, 2.65 FIP, 4.9 fWAR)
• Kevin Gausman (SF; 33 GS, 192 IP, 2.81 ERA, 3.00 FIP, 4.8 fWAR)
• Robbie Ray (TOR; 32 GS, 193.1 IP, 2.84 ERA, 3.69 FIP, 3.9 fWAR)
• Clayton Kershaw (LAD; 22 GS, 121.2 IP, 3.55 ERA, 3.00 FIP, 3.4 fWAR)
• Marcus Stroman (NYM; 33 GS, 179 IP, 3.02 ERA, 3.49 FIP, 3.4 fWAR)
• Anthony Desclafani (SF; 31 GS, 167.2 IP, 3.17 ERA, 3.62 FIP, 3.0 fWAR)
• Steven Matz (TOR; 29 GS, 150.2 IP, 3.82 ERA, 3.79 FIP, 2.8 fWAR)
• Alex Wood (SF; 26 GS, 138.2 IP, 3.83 ERA, 3.48 FIP, 2.5 fWAR)
• Alex Cobb (LAA; 18 GS, 93.1 IP, 3.76 ERA, 2.92 FIP, 2.5 fWAR)
• Jon Gray (COL; 29 GS, 149 IP, 4.59 ERA, 4.22 FIP, 2.3 fWAR)
• Rich Hill (TB/NYM; 31 GS, 158.2 IP, 3.86 ERA, 4.34 FIP, 1.7 fWAR)
• Danny Duffy (KC; 12 GS, 61 IP, 2.51 ERA, 3.40 FIP, 1.6 fWAR)
• Corey Kluber (NYY; 16 GS, 80 IP, 3.83 ERA, 3.84 FIP, 1.5 fWAR)
• Zack Greinke (HOU; 29 GS, 171 IP, 4.16 ERA, 4.71 FIP, 1.3 fWAR)
• Yusei Kikuchi (SEA; 29 GS, 157 IP, 4.41 ERA, 4.61 FIP, 1.1 fWAR)
• Noah Syndergaard (NYM; 2 GS, 2 IP, 9.00 ERA, 7.67 FIP, 0.0 fWAR)
• Justin Verlander (HOU; N/A)

As we say, this is only a partial list of the players who could be available, but there are interesting names up and down this list. Scherzer certainly tops the list, and not only is he the most talented pitcher available in free agency this winter but he also does not have draft pick compensation attached to him as he was traded midyear. On top of that, as he heads into his age-37 season it would not take a large commitment in terms of years. Putting him at the top of a rotation followed by Eovaldi and Sale would be a huge development for this roster.

Beyond Scherzer, more question marks start to pop up. Both Verlander and Syndergaard are intriguing coming off Tommy John surgery, but it’s hard to know what we can really expect from either of them coming off long layoffs. Both also received qualifying offers, so if they decline the Red Sox would have to give up a pick to get them. It wouldn’t be a first rounder which helps the cause, and I can’t say definitively they should back off without knowing just how healthy they look (Verlander in particular), but I am a bit hesitant.

Stroman, meanwhile, is probably my favorite pitcher from his tier in a vacuum, but we don’t exist in a vacuum. He’s a pitcher who relies on weak contact, and particularly weak contact on the ground. That is not a good fit with this infield defense. Pitchers like Desclafani, Wood, and Cobb would feel underwhelming as top options, though would be ideal secondary signings after the top options.

If I had my druthers, I’d love to see a Scherzer/Matz pairing, though I’m not sure I’m expecting that much to be spent at this position. Still, I wouldn’t rule it out with Scherzer for the reasons mentioned above.

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Potential Trade Partners

• Cincinnati Reds: The Reds are open for business as they look to shed salary, and both Luis Castillo and Sonny Gray could be top starters moved.
• Miami Marlins: The Fish have a bit of a young pitching glut which they could look to move to help elsewhere, with Pablo López and Elieser Hernandez the most likely names to be moved.
• Oakland Athletics: They are also looking to cut salary, with Sean Manaea and Chris Bassitt potentially on the move.
• Chicago Cubs: What the North Siders are up to this winter is less clear, but if they keep selling Wade Miley could be available and maybe they could be talked into a Kyle Hendricks buy low.
• Colorado Rockies: Is it really an offseason if we don’t talk about German Márquez?
• Baltimore Orioles: Perpetual sellers, they could put John Means on the market.
• Kansas City Royals: They seem on the way up, but Mike Minor or Brad Keller could be intriguing buy lows.
• Detroit Tigers: Matt Boyd is an interesting talent, though his health is an open question.
• Pittsburgh Pirates: Mitch Keller feels like he could be the next former Pirates prospect to break out after leaving the organization.

Whenever this hot stove does get moving, there are a few starting pitchers who could be big splashes. Castillo tops the list and is a prime Yankees target, which means the Red Sox grabbing him would be that much sweeter. I don’t see that happening, though, as I’m not sure Boston’s front office is going to want to pay the prospect price for the top-tier names at this point. Maybe in a couple years, but not this winter. I think they could look at some of these secondary names, though. Means and Mitch Keller stand out the most to me, though their respective clubs would have to be talked into a deal as neither team has to make a move.