Jordan Montgomery

Jordan Montgomery was the fourth Baby Bomber nobody talked about -- a lanky lefty out of South Carolina who quietly anchored the back of the New York Yankees rotation from 2017 through 2022, got traded away before he ever got to pitch deep into October in pinstripes, and then won a World Series ring with someone else within fourteen months. Funny how that works out sometimes.

Path to the Bronx

The Yankees took Montgomery in the 4th round of the 2014 draft, 122nd overall, out of South Carolina, where he'd gone 20-7 across three seasons and posted a 1.48 ERA as the Gamecocks' ace in 2013. He signed for a modest $424,000 bonus -- the kind of pick nobody writes prospect rankings about.

He debuted on April 12, 2017, against Tampa Bay, and it wasn't smooth: a two-out walk to Evan Longoria set up a two-run homer to Rickie Weeks in the first inning. Montgomery settled in from there (rookies don't get much of a grace period in the Bronx), went 4.2 innings, struck out seven, and the Yankees rallied to win 8-4. Five days later he picked up his first career win against the White Sox.

Yankees Career

That 2017 rookie season turned into the real story. Montgomery went 9-7 with a 3.88 ERA over 29 starts, and led all AL rookies in starts, strikeouts, and innings pitched -- on a team that gets remembered for Aaron Judge and Gary Sanchez hitting moonshots, not for the rookie lefty holding down the fourth spot behind them.

Then came the injury that would define the rest of his career. Six starts into 2018 -- 2-0, 3.62 ERA, looking like a guy building on his rookie year -- he left an outing against Houston after a single inning with a forearm strain. Tommy John surgery followed on June 7, 2018. He'd pitch a total of four innings, in one relief appearance, over the next fifteen months.

Monty came back for good in 2020, and his first fully healthy season since the surgery, 2021, was his best as a Yankee: 6-7, 3.83 ERA, 157.1 innings, a full-time rotation piece again. His lone career postseason start as a Yankee came in a much bigger spot -- Game 4 of the 2020 ALDS against Tampa Bay, a win-or-go-home game. He gave the Yankees four innings of one-run ball, and New York won 5-1 to force a Game 5 (which they'd go on to lose). He'd actually been on the 2017 ALDS and ALCS rosters too, but never got into a game -- so that 2020 outing stands as the only postseason inning he ever threw in pinstripes.

By August 2, 2022, with the Yankees 21 starts and a 3-3, 3.69 ERA into his season, the front office moved him -- straight up, for outfielder Harrison Bader. Montgomery said he was "pretty shocked," adding, "This is my family. It's all I know. I've been playing with the same guys for years." Six years in one organization will do that to you.

What Happened Next (Briefly)

The Cardinals flipped him to Texas at the 2023 deadline, and Montgomery caught fire down the stretch: a Game 7 ALCS win in relief at Houston, a World Series Game 2 start, and a ring as the Rangers won it all. Because he'd arrived mid-season, Texas couldn't even tender him a qualifying offer that winter -- a rules quirk that helped make his free agency drag deep into spring training. The Yankees floated interest in a reunion that same offseason (the same winter they traded for Juan Soto, though the two are unrelated -- Montgomery was never part of that deal), but he chose Arizona instead, then endured a rough 2024 and a second Tommy John surgery in March 2025. He signed back with Texas in February 2026, still rehabbing.

He never got the deep Yankees playoff run his rookie season promised. But the guy who spent six years as the answer to a Bronx trivia question -- "wait, who was the fifth starter again?" -- ended up with a ring anyway. Just not the one anybody in the Bronx was rooting for.