Aaron Judge has put together a Yankees career that most players only dream about. He owns three MVP awards, and he’s established himself as one of the greatest right-handed hitters the game has ever seen. But there’s still one glaring gap in the résumé: no championship.
That’s the part that stings when you look around at some of the teammates who’ve already picked up rings elsewhere. Baseball is a team game, of course, and nobody is handing out a title to one player alone. Still, it has to be a little annoying for Judge to watch former Yankees celebrate a World Series before he’s ever gotten that moment.
Ben Rortvedt is one of the stranger names on that list. For a long time, there was almost a mystery around him after he came over as a throw-in in the Josh Donaldson trade.
The hope was that he might grow into at least a useful backup catcher, maybe even more. Instead, the main thing people had to work with for a while was a single photo of him flexing a massive bicep.
Then 2023 happened. Rortvedt became Gerrit Cole’s catcher and played a part in Cole winning his first Cy Young.
There was even one game where Cole was seen in a heated argument with Rortvedt over something. Their working relationship drew enough attention that it became a talking point during the season.
That was also Rortvedt’s final year with the Yankees. After that, he bounced around between Tampa Bay and Los Angeles.
He got a few postseason at-bats, but never an official World Series at-bat. Even so, the contrast is hard to miss: Cole’s night in Game 5 ended with his team unraveling defensively, while Rortvedt walked away with a ring.
Andrew Heaney’s Yankees stint was memorable for the wrong reasons. He was a big part of why the Yankees ended up playing the Wild Card game at Fenway Park instead of River Avenue in the Bronx in 2021, and his run in New York after the trade was rough. But he eventually found another gear somewhere else.
He spent 2022 with the Dodgers, then won a World Series with the Rangers the next year. In the World Series, he delivered a strong start, throwing 5.2 innings and allowing one run against the Diamondbacks. That kind of outing was probably what the Yankees had hoped for, but they had already designated him for assignment before the 2023 season was over.
Gary Sanchez’s path has been a lot messier. He was once one of the best catchers in baseball, but everything changed in 2018 when his production fell off. From there, he had a tense relationship with fans and the media, and the lazy label followed him around even though that ignored how demanding it is to catch and manage an entire pitching staff.
Judge and Sanchez were supposed to be part of the Yankees’ push toward a World Series. Instead, Sanchez got his ring before Judge did. At Sanchez’s lowest point, it even felt like he might not be in the big leagues much longer.
Jake Bauers also ended up with a championship, and unlike Sanchez, he had a meaningful role in the postseason run. He was huge in the NLCS, tearing through the Dodgers’ pitching staff. Bauers had been part of a 2023 Yankees team that missed the playoffs, and while his season in New York wasn’t especially strong, there were flashes of what he later became for the Brewers.
There was also a time when Bauers thought he might retire, which makes the ring feel even more meaningful. He hung on, and it paid off. He’s one of the good guys in the game, and he deserved it.
Then there’s Jordan Montgomery, whose postseason run with the Rangers may have been the loudest reminder of what the Yankees let get away. The Yankees traded him for Harrison Bader, and Bader was later cut in 2023 before the Cardinals dealt Montgomery to Texas. That trade ended up becoming the biggest in Rangers history.
Montgomery was excellent in that postseason. Over 31 innings, he posted a 2.90 ERA, went 3-1 in five starts, and finished with a 17-to-5 strikeout-to-walk ratio.
That run helped land him a huge deal with the Arizona Diamondbacks, though things went downhill after that. He later fired Scott Boras for giving him bad advice, and his career hasn’t been the same since.
But he still has 2023, and that’s something.
In Other News...
Yankees Risk Another Costly Fit Chasing Right-Handed Help For Judge
The Yankees are already looking at ways to reshape the offense around Aaron Judge after another early postseason exit, and the front offices thinking is clear: add more right-handed power to create a better balance in the lineup. One name that has surfaced is Teoscar Hernandez, a Dodgers outfielder who brings World Series experience and the kind of pop that can change a game in a hurry.
But the fit is not as simple as the profile suggests. Hernandez comes with defensive concerns, a hefty salary for one guaranteed season, and some recent decline in home run production, which makes him a more complicated answer than a clean one. For a Yankees club trying to support Judge without boxing itself into another expensive mistake, the appeal is obvious, but so are the risks. [Read more 🡒]
Yankees Are Being Warned Away From 3 Tempting Trade Targets
The Yankees offseason shopping list is being narrowed by more than just price tags. As the front office weighs ways to add impact without clogging up the roster, three names that might look appealing on paper are drawing caution for different reasons: CJ Abrams, Hunter Goodman and Spencer Torkelson each bring a skill set that could fit a contender, but each also comes with enough baggage to make the fit less clean than it first appears.
Abrams would require the Yankees to buy into both his bat and his defensive value while also paying a premium to land him. Goodmans power is eye-catching, but his strikeout issues and the Coors Field effect make the numbers harder to trust. Torkelson, meanwhile, runs into a different problem entirely, because the Yankees already have enough depth at first base and designated hitter to question whether he would actually solve anything. For a club trying to build around younger internal options, the better move may be to keep the runway clear for players like George Lombard Jr. and Spencer Jones. [Read more 🡒]
Yankees Prospect Dax Kilby Is Forcing A Much Bigger Conversation
Dax Kilbys Arizona Fall League showing is doing more than easing any lingering concern about the hamstring injury that wiped out most of his 2026 season. The Yankees prospect has looked sharp at the plate, hitting .288/.350/.558 with two home runs through 13 games, and the performance has come with noticeable swing adjustments that suggest this is more than a simple hot streak.
Eric Longenhagen has already taken notice, praising Kilby and projecting him as a potential top-20 prospect in upcoming rankings. For a player who spent much of the year sidelined, that kind of momentum matters, because it puts Kilby back into a conversation the Yankees would much rather have now than later: how quickly his talent can translate into a real rise through the system. [Read more 🡒]