That time Derek Jeter played against the Yankees
Aaron Judge was recently announced as Team USA’s captain for the 2026 World Baseball Classic, becoming the first player to commit to Mark DeRosa’s squad.
Judge has never previously represented his country, having missed the last WBC while drying the ink on his nine-year, $360 million free agent contract.
But in less than 12 months, he will lead the US into battle – against my Great Britain, no less. Somewhere, George Washington smiles.
Judge will not be the first Yankee captain to play for Team USA at the WBC. That distinction, like so many, belongs to the legendary Derek Jeter, who headlined the American effort in 2006 and 2009. The latter conjured a fascinating anomaly, as Jeter played against the Yankees for the only time in his career, which spanned more than 3,000 games, including exhibitions and playoffs.
The incongruous matchup occurred at George M. Steinbrenner Field, on 3 March 2009, during spring training. Jeter hit second for a US team featuring Chipper Jones, David Wright, Jimmy Rollins, Ryan Braun, Dustin Pedroia and Evan Longoria. Having represented the US in 2006, Álex Rodríguez switched allegiances to the Dominican Republic, adding a fresh wrinkle to his complicated relationship with Jeter. Davey Johnson managed the star-spangled assemblage, with the Yankees tabbed for a pre-tournament tune-up.
The game was strange for everyone involved. That morning, Jeter worked out in the Yankees’ weight room, before pinstriped manager Joe Girardi playfully kicked him out of the clubhouse. “We’re going to drill him,” kidded Jorge Posada, Derek’s longtime teammate. “It’s the first time we’ve ever played against each other.”
Jeter likened the occasion to an ‘intrasquad game,’ although his role on Team USA involved brokering détente between ostensible rivals. Rollins and Wright sat either side of Jeter in the clubhouse, fielding quips about the Phillies-Mets feud. “If they want to get at each other, they have to come through me,” said Jeter, ever the diplomat. Maybe Switzerland needed a shortstop, too.
Before the game, Girardi ordered his Yankees to pitch outside to Jeter, avoiding unnecessary injuries on inside jam-shots. When Phil Hughes’ first pitch to Captain America leaked out over the plate, Jeter smiled and Yankee catcher Kevin Cash leapt to an impromptu mound visit. Derek then grounded out, jogging past the Yankee dugout to gentle razzing.
The Yankees went ahead in the first, when Posada singled in a run as the designated hitter. Team USA struck back in the third, though, with Jeter – who else? – cracking a two-run single up the middle. Understandably confused, the YES Network scorebug tallied Jeter’s RBI in the usual Yankee column, flashing a 3-0 lead before correcting the error.
All told, Jeter went 2-for-4 with a walk in a 6-5 US victory before a crowd of 8,822 – the only 8,822 people, ever, who watched #2 play against the Yankees. “It was strange running to the other dugout,” Derek admitted after playing all nine innings. “I almost ran to the other side a couple times.”
Following the Yankee contest, Team USA played exhibitions against the Blue Jays and Phillies – losing to Toronto and beating Philadelphia – before embarking on a pressurised WBC campaign.
Led by Jeter – who hit .276 with a .382 OBP in eight games – the US progressed to the semi-finals before falling to Japan, the eventual champions.
Famously, Jeter then returned to lead the Yankees to a World Series championship in 2009, christening the new Yankee Stadium in its inaugural year by beating Rollins’ Phillies in the Fall Classic.
Maybe Judge should arrange a Team USA exhibition against the Yanks in 2026, then. Marcus Stroman is an excellent batting practice pitcher, after all.
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* Fun fact: I have met, and have baseballs signed by, five people mentioned in this piece – Jeter, DeRosa, Wright, Rollins and A-Rod. My wife, Patrycja, had Rollins sign a second ball during the 2024 Phillies-Mets London Series. The only problem? Informed of the duplicate in our collection, she kindly gave the Rollins baseball to a red-capped fan in the bleachers. So? Well, Patrycja did not see the insignia on that red cap up close, and the guy was actually a Cardinals fan. He was grateful, if a little perplexed, while some of the Philly faithful surrounding us were aghast. Still, it is the thought that counts, I guess.
