4 back-up free agent targets for the Red Sox with Sonny Gray off the market

With Sonny Gray off the market, the Red Sox need to strike on the starting pitching market before it is too late.

Texas Rangers starting pitcher Jordan Montgomery (52) throws a pitch against the Arizona
Texas Rangers starting pitcher Jordan Montgomery (52) throws a pitch against the Arizona / Rob Schumacher/The Republic / USA TODAY
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With the news yesterday that the Cardinals signed Sonny Gray to a three year deal, the pressure is now on the Boston Red Sox to deliver on the promise of getting this rotation sorted out. For the early portion of the offseason, the starting pitching market had been (mostly) frozen as teams await the free agency decisions from Shohei Ohtani and Yoshinobu Yamamoto. However, the market is clearly beginning to thaw with Gray's signing as well as, to a lesser degree, Kenta Maeda's deal with the Tigers.

The start of the Winter Meetings is less than a week away and it is more and more likely that we will start to see more free agent movement in the lead up to them. With Gray no longer available, Boston is going to have make their move(s) soon for rotation help or risk getting the league's leftovers this offseason. Given how poorly the Red Sox's rotation performed in 2023, having that happen would be a disaster.

Here are some of the best Sonny Gray alternatives for the Red Sox on the free agent market

Boston wasn't ever a favorite to land Sonny Gray as it seemed like their aspirations were for locking up a starter on a longer term deal. Gray had a fantastic 2023 season, but he is a little older and his injury history does give one some pause. However, his departure from the market limits Boston's options and could force their hand soon as to what arms they prefer and make new front office head Craig Breslow make a decision fairly quickly.

Let's take a look at the best starter free agent options for the Red Sox now that Sonny Gray has signed elsewhere.

Yoshinobu Yamamoto

Much is going to be made of Shohei Ohtani and his possible connection with Boston this offseason and frankly, that is understandable as he is a generational talent. However, the focus here is going to be on arms that can help the Red Sox on the mound in 2024 and with Shohei not pitching next season, the biggest name left that could be in Boston's rotation next season is Yoshinobu Yamamoto.

From the moment that Yamamoto was posted, he became one of the top players on the free agent market period despite the fact that he has yet to play a single inning in MLB. He has dominated over in Japan the last couple of years thanks to a tantalizing blend of stuff including a mid to upper 90's fastball as well as a devastating splitter and curve and the ability to command his pitches. Guys with this kind of upside who are also just 25 years old almost never hit free agency.

Ever since it was rumored that he was coming to MLB, Boston has been mentioned among the teams that are going to be in on Yamamoto. He certainly isn't going to come cheap as most outlets have him getting AT LEAST seven years and north of $200 million, but he is worthy of that investment and Boston clearly has to get serious about investing in their rotation this offseason.

Shota Imanaga

While not nearly as well known as Yamamoto, Shota Imanaga is another Japanese pitcher coming over to MLB that was only just posted yesterday. Given that the Red Sox may need to add more than one starter this offseason, Imanaga needs to be on Boston's radar as a guy that could really help the backend of the Red Sox's rotation while not costing so much as to prevent the team from acquiring another quality arm.

Imanaga's stuff isn't nearly as flashy and Yamamoto's as he is a command over stuff guy who throws his fastball in the low 90's from the left side along with a split changeup and a pair of breaking balls. He doesn't walk a ton of batters and still has found ways to miss bats over in Japan despite not possessing overpowering stuff. He is going to require a high eight figure deal in all likelihood over (probably) five years or so, but that is more than reasonable given the cost of good starting pitching in free agency these days.

However, Imanaga doesn't come without some risk. In addition to not have the raw stuff to overpower hitters which could be problematic when he goes up against MLB hitters, Imanaga is already 30 years old. We have obviously seen pitchers dominate in the league into their late 30's and beyond (see: Justin Verlander, Clayton Kershaw, and Max Scherzer), but a certain amount of caution needs to be exercised when it comes to how long of a deal should be handed out to a guy that already has some mileage on his arm and has yet to play in the majors.

Marcus Stroman

One name that hasn't been mentioned enough this offseason and a potential game-changing rotation arm is Marcus Stroman. Sure, he is not coming off a season like Jordan Montgomery (more on him shortly), Blake Snell, or Gray had, but he is just one of those guys that puts up consistent results year in and year out that could be a major boost to Boston's rotation.

It was somewhat surprising to see Stroman opt out of his deal with the Cubs and leave $21 million on the table, but he is clearly betting that the current market for starting pitching is going to play in his favor. For the vast majority of his career, Stroman has been a lock to post a 3ish ERA, miss an okay amount of bats, and get a TON of soft groundballs. While a pitcher who has the ball put in play against him a decent amount isn't completely ideal given the state of the Red Sox's infield defense, it should certainly help that the quality of contact against Stroman is usual very poor.

Given that Stroman left a guaranteed $21 million in Chicago, he is probably going to be looking for at least a three or four year deal especially considering that it is likely that his is going to be his last chance at a big pay day at 32 years old. However, it wouldn't be the first time that Craig Breslow was in a front office that targeted him as Breslow was a key voice on the Cubs' pitching decisions when Stroman signed with Chicago back in 2021.

Jordan Montgomery

Finally, we come to Jordan Montgomery who should absolutely be near the top of the Red Sox's wish list this offseason. Among the free agent starting pitchers this offseason, no pitcher helped their stock more in 2023 than Montgomery as he is now positioned as one of the top arms available period after being perennially under-appreciated in his career.

Aside from the fact that all the guy does is post at least a low 3 ERA each season while throwing a ton of strikes every year since 2020, Montgomery has a lot going for him. His fastball grades out well despite the fact that he doesn't throwing particularly hard which should appeal to Boston's new front office, he is coming off a career best season where he was an integral part of the Rangers' run to a World Series title, and he doesn't have a qualifying offer attached to him as he wasn't eligible to receive one at the end of the season.

While the secret is out on Montgomery now and most of the league is trying to convince him to join their ranks, Boston does have some advantages in the chase to acquire him. Not only do the Red Sox have a ton of young talent coming up from the minors which points to a bright future for the team, but Montgomery is already living in the Boston area as his wife dermatology career has fortuitously brought them nearby. Monty isn't going to leave a bunch of money on the table just because of that, but it does seem to be a point in Boston's favor.

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