Sonny Gray

The New York Yankees traded three prospects for Sonny Gray at the 2017 deadline expecting a frontline starter. For about ten weeks, that's exactly what they got. Then 2018 happened, and by the time Cashman shipped him to Cincinnati that January, the read on Gray's Bronx tenure had flipped from "difference-maker" to "case study in a guy who never looked right at Yankee Stadium." Both versions of that story are true, which is the annoying thing about Sonny Gray.

The Trade

Oakland made Gray available ahead of the July 31, 2017 deadline, and the Yankees won the bidding: Dustin Fowler, Jorge Mateo, and James Kaprielian went west, plus $1.5 million in international bonus pool money, for a pitcher who was 6-5 with a 3.43 ERA in 16 starts and already a former All-Star (2015, when he went 14-7 with a 2.73 ERA and finished third in AL Cy Young voting). It looked like a fair price for a guy entering his prime. Fowler had already blown out his knee on his major league debut two months earlier and Kaprielian had just had Tommy John surgery -- so from the outside, the Yankees were selling high on two guys who couldn't play anyway. Good process, at least on paper.

Gray made 11 starts down the stretch and went 4-7 with a 3.72 ERA, solid enough to earn him the ball for Game 1 of the ALDS against Cleveland. That one went badly -- 3.1 innings, 3 earned runs, four walks, a 4-0 loss. Twelve days later he got a do-over in ALCS Game 4 against Houston and delivered: one run, one earned, over five-plus innings in a 6-4 Yankees win that evened the series at two. That's the version of Gray the front office paid for. It just didn't show up nearly enough.

2018: The Year It Fell Apart

Aaron Boone's first Yankees team won 100 games, and Gray was supposed to be part of why. Instead his ERA split almost exactly down a home/road line that still looks like a typo: 3.17 on the road, 6.98 at Yankee Stadium. Something about pitching in the Bronx -- the short porch, the pressure, take your pick -- never clicked for him. By August 1, he'd allowed seven runs in under three innings against a last-place Orioles team, his ERA sitting at 5.56, and Cashman had seen enough. Lance Lynn took his rotation spot the next day; Gray finished the year working out of the bullpen, a stretch complicated further when an old, offensive tweet from his minor league days resurfaced and he briefly went dark on social media. The Yankees left him off the 100-win team's ALDS roster that October. For a guy who'd been an All-Star three years earlier, that's about as sharp a fall as it gets.

The full-season Yankees line -- across 2017 and 2018 combined -- was 15-16 with a 4.51 ERA over 195.2 innings, 182 strikeouts. Respectable-looking on a stat sheet. Miserable to actually watch some nights.

Where He Went After

The Yankees moved on that January, sending Gray to Cincinnati in a three-team deal (Seattle also involved) that netted New York outfield prospect Josh Stowers. The Reds immediately locked Gray up on a three-year extension, and it worked out well for both sides -- he made an All-Star team there in 2019. Three years later Cincinnati flipped him to Minnesota for pitching prospect Chase Petty, and Gray kept climbing: 2023 with the Twins was the best season of his career, 8-8 with a 2.79 ERA (second in the AL) and 183 strikeouts, good for AL Cy Young runner-up. He lost that award to Gerrit Cole -- the same Yankees rotation Gray never quite fit into. The Cardinals signed him to a three-year, $75 million deal that November.

Gray later took some shots at how the Yankees tried to get him to pitch, saying the org pushed him toward a breaking-ball approach that didn't suit his stuff. Cashman disputed the characterization, and the underlying numbers are murkier than a clean "they broke him" narrative -- but something about pitching in pinstripes clearly never fit right, and Gray's the first to say so.