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Read Full BioDerek Jeter knows better than anyone what it takes to lead a successful baseball team.
Jeter — known as “The Captain” — led the New York Yankees during their last dynasty years at the turn of the millennium, leading the franchise to five championships between 1996 and 2009. From 2003 until his retirement in 2014, Jeter was the captain of the Yankees, the franchise with the most media attention and the highest expectations of any organization in MLB.
Fast forward more than a decade, and not much has changed in terms of expectations. However, the Yankees are no longer the center of the baseball universe. That spot is now reserved for the Los Angeles Dodgers.
The Dodgers are the defending World Series champs, fresh off an epic seven-game series win over the Toronto Blue Jays. They’ve now won three World Series in the past six seasons and back-to-back championships.
When asked if he could see the Dodgers mimicking the success of his Yankees teams, Jeter said they’ll be “heavy favorites,” but a lot of breaks have to go your way in addition to that.
“We’ll see,” Jeter told Casino Beats in an exclusive interview. “I’m sure they’ll be heavy favorites again to win. When you have a great team, you also have to have a lot of breaks. In four of our first five years, we got a lot of breaks. Great teams make their own breaks, but a lot of things have to go your way as well.”
Meanwhile, Jeter’s former team is looking just to break through the ceiling to win a World Series. New York advanced to the World Series in 2024, its first appearance since Jeter led the way in 2009. However, it became clear they were outmatched against the Dodgers when they lost in five games.
The Yankees are coming off another solid season, tying for the most wins in the American League with 94. However, they regressed in the postseason, losing in the AL Division Series in five games to the Blue Jays.
Jeter stresses that the key for a contending team in every season is the moves you make at the trade deadline. It’s something that will likely be key for the Yankees during the 2026 season while they play in arguably the toughest division in baseball in the AL East. Both the Jays and the Boston Red Sox made it to the playoffs last season, and the Baltimore Orioles are expected by many to return as contenders.
“They’ll always be in it,” said Jeter of the Yankees. “I think the separator for every team is the trade deadline. A lot of times you got different teams. The Dodgers, they didn’t have different players, but a lot of players were hurt, and they got healthy in the second half, so it’s almost like they made acquisitions.
“It all boils down to what happens throughout the course of the season, but the Yankees will be right there,” Jeter continued to say. “I’m sure they’re going to be one of the favorites to win the American League into the postseason. But it’s a lot that goes into the next six months.”
Jeter: Gerrit Cole as ‘Good as Anyone’ When Healthy
When the topic of former AL Cy Young winner Gerrit Cole returning is brought up and how big of an impact he’ll make, Jeter agrees that it’s key. Cole missed the entire 2025 season after undergoing Tommy John surgery.
The Yankees’ pitching took a major hit as a result, ranking 16th in MLB in runs allowed at 685. Meanwhile, the offense was explosive, leading the league in home runs and runs. However, it wasn’t enough due to Cole’s absence and the pitching staff’s mediocre performance.
“Always, you win with pitching,” Jeter said. “That’s how you win — you pitch. There aren’t too many 10-9 games in the playoffs. You can win that way in the regular season. When you get into the postseason, you gotta be able to pitch. Gerrit, when he’s healthy, he’s as good as anyone. He’ll be a welcome addition back whenever he comes back.”
Jeter Sees Shades of Dave Winfield in Aaron Judge
One constant for the Yankees is Aaron Judge‘s continued production. The 33-year-old showed he isn’t slowing down anytime soon, winning his third AL MVP and first batting title with a .331 batting average in addition to hitting 53 home runs. Judge has been the captain of the Yankees since the 2023 season.
“I think our relationship has grown over the last couple of years,” said Jeter of Judge. “He obviously came up when I retired. I didn’t know him well, but I’ve gotten the chance to get to know him over the last couple of years. What he’s done on the field goes without saying. Just keeps getting better and better. I think the challenge when you’re like Aaron is to keep doing it year in and year out, which is tough. You know how it is for the Yankees, it all boils down to October.”
When asked to make a player comparison for Judge — who is 6-foot-7 and 260 pounds — Jeter immediately mentions Dave Winfield, a 12-time All-Star who is in the Baseball Hall of Fame. Winfield was 6-foot-6, 220 pounds, and starred for the Yankees for a number of years. He once hit .322 and 34 home runs in a single season.
“Dave Winfield comes to mind. Winfield is in the Hall of Fame; he was actually my favorite player, too,” said Jeter. “You don’t see too many players that size. But Aaron separates himself — he doesn’t just hit home runs — he also hits for average.”
Brian Cashman, who has been the Yankees’ general manager since 1998, when Jeter starred for the franchise, is still leading the baseball operations to this day. Jeter doesn’t talk with Cashman often because he’s not afililated with the franchise. Jeter currently works as an analyst during FOX broadcasts of MLB games.
“From time to time,” said Jeter on whether he talks to Cashman. “I have no position with the Yankees and the organization. I speak to him, and we run into each other once in a while.”
Jeter Serves as Ambassador for Padel ‘Reserve Cup Series’
Jeter appeared at the Reserve Cup Series in Miami, an annual tournament created by Wayne Boich in 2024 featuring the best padel players in the world. Jeter is considered a team captain and serves as a sort of ambassador for the Reserve Cup.
Padel is one of the fastest-growing sports. It’s a variation of tennis, but it features a glass wall and is much faster-paced. Furthermore, it tends to be contested in two-on-two matchups.
“You have to be more athletic to play this sport,” said Jeter. “It’s not just standing in a little, small area to hit the ball over the net. You gotta be able to move around, and it’s challenging, man. When you see an event like this, you see the best in the world do it, and how athletic it is, and how much athleticism it takes to play, and it’s fun to watch.”
When asked whether he plays padel, the 51-year-old Jeter said his involvement in sports is limited these days.
“I don’t do much physically anymore in terms of sports,” said Jeter. “I’m trying not to get hurt. I’ll golf every once in a while. Wayne tried to get me out there, but I haven’t been out there yet.”
