Sonny Gray spent nearly two seasons with the New York Yankees, but that didn't change his mindset of playing in the Bronx. It's no secret that some players are better off avoiding the bright lights of New York altogether. Gray is one of those, and made it perfectly clear on Tuesday.
The Red Sox traded for Gray just a week ago. In his first public comments since that move, Gray pandered to a fanbase that loves nothing more than to troll its rivals to the south.
Sonny Gray wasted no time getting on Red Sox fans' good side
Gray was acquired by the Yankees at the 2017 trade deadline. In 2017 and 2018, he accumulated just 1.1 bWAR, and left New York after a disastrous-by-his-standards 4.90 ERA in his final season. From there, Gray revived his career with the Reds, Twins and finally Cardinals, but never forgot his spell in the Bronx, and why it went so horribly wrong.
“When I was there (from mid-2017 through 2018), it just didn’t really work for who I am," Gray said.
Newest Red Sox Sonny Gray on his time with the Yankees:
— MLB Network (@MLBNetwork) December 2, 2025
“I never wanted to go there in the first place.”#MLBNHotStove pic.twitter.com/Nz3siNwUpL
Gray wore a 2007 Red Sox World Series hat to his introductory call with Boston media – and if you think that won't make a difference with that crowd, then you don't know the vibe around Beantown. Appearances matter, and in this case, Gray got off to a roaring start.
“What did factor into my decision to come to Boston, it feels good to me to go to a place now where, you know what, it’s easy to hate the Yankees, right?” Gray continued. “It’s easy to go out and have that rivalry and go into it with full force, full steam ahead. I like the challenge.”
And make no mistake about it, Gray will be challenged in Boston. Sure, it's a slightly smaller media market than the Big Apple, but not by much. Red Sox fans are as demanding as any in the sport, and Gray is not who they imagine as their No. 2 starter behind Garrett Crochet come Opening Day.
The Red Sox have to add another starting pitcher, no matter the cost

While the Red Sox were just fine adding Gray's salary for a cheaper return, they'll have to do more if they plan on competing in the AL East and for a World Series in 2026. Sean McAdam of MassLive warned Red Sox fans not to get their hopes up in free agency, as this is a front office that's been instructed to take calculated risks, rather than expensive ones.
"According to industry sources familiar with the organization’s thinking, the Red Sox are OK going over the first CBT threshold — set at $244 million for 2026 — which would translate to them absorbing a modest financial loss. But with anything beyond that, there’s a reluctance to incur bigger deficits," McAdam wrote.
Boston's payroll is already around $223 million, per FanGraphs. That means they have about $21 million to spend, barring a trade of Masataka Yoshida. And they still hope to re-sign Alex Bregman this winter, as well.
With all this in mind, the Sox best chance at adding another frontline starting pitcher could come via trade. Look no further than the ace picture below, Minnesota Twins pitcher Joe Ryan.
What would it take to acquire Joe Ryan?

The asking price for Ryan is said to be high, as it should be. He was shopped at the trade deadline back when Minnesota was still hoping to sell off its assets for a higher franchise valuation (yes, really). However, now that the Pohlads are said to be keeping the team as is, trading Ryan actually makes a little more sense.
The Twins are going nowhere fast. A rebuild is on the horizon, and Ryan and Byron Buxton could very well be dealt this winter. ESPN's Jeff Passan and Kiley McDaniel ranked Ryan as the sixth-best trade asset this offseason. He has an elite fastball and posted a 3.42 ERA last season. He also has two years left on his contract. which means his value won't get any higher than it is now.
Thankfully for the Red Sox, they have a surplus of farm system talent. Any deal for Ryan likely won't include players such as Roman Anthony, Marcelo Mayer or Franklin Arias, but Boston's deep system allows them the opportunity to trade from positions of strength. Jhostynxon Garcia, for example, could be a great fit in Minnesota whether they decide to hang onto Buxton or not.
Ryan's contract and potential as a high-level No. 2 starter make him worth the risk. It's up to Breslow to pull the trigger, and save financial assets in the process.
