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In 1998, the Yankees capped a truly historical season by sweeping the Padres in the World Series. Twenty-five years later, both teams met again for a regular season weekend series in the Bronx. New York took two of three.

What was rarely discussed over the weekend, however, was the 25-year anniversary of that Fall Classic. How the Yankees, despite being the clear favorites, trailed in Games 1 and 3 before rallying to win? Or how about the Padres winning 98 games and the NL West, and then slaying the 102-win Astros and then the 106-win Braves in the playoffs?

Fast forward 25 years later and the question presents itself: will there be a Yankees-Padres World Series rematch? Expanded playoffs change everything but even so, the standings present a tall order. New York is third in the AL East and seven games behind first-place Tampa Bay. San Diego is fourth in the NL West, 7.5 games behind the first-place Dodgers, and are MLB’s second-worst hitting team.

Not exactly a recipe for a championship, even though plenty of games remain.

Except if we look back at 1998, those Padres weren’t a great batting team by that day’s standard either. They hit .253 on the year which, in the Steroid Era, made them fifth-worst in the league. The Yankees ranked third and hit .288 as a team but, again, that was a historically unprecedented season and, quite possibly, the greatest overachievement in sports history. New York was still a good team, but maybe not 114 wins good.

The fact of the matter is that much like today, even with how well the Yankees hit in ’98, both teams’ greatest strength was actually pitching. The Padres’ arms were actually better than the Yankees’, ranking third in MLB with a 3.63 ERA. New York’s pitching, in turn, ranked sixth with a mark of 3.82.

Thus, what would happen if both the Yankees and Padres rallied in 2023 and faced off in the World Series? It’d probably be a closer World Series and, dare we say, better, even without two Hall of Fame stoppers in Mariano Rivera and Trevor Hoffman.

It all comes down to the teams’ star-studded lineups and their high-scoring potential. The Padres have a deeper lineup featuring feared sluggers in Juan Soto, Manny Machado, Fernando Tatis Jr., and Xander Bogaerts. They’d match up beautifully against Aaron Judge, Anthony Rizzo, and Giancarlo Stanton in a playoff setting.

The pitching matchups speak for themselves. Gerrit Cole vs. Yu Darvish would be must-see despite Darvish’s playoff struggles. Both sides also have fantastic big-game pitchers in Joe Musgrove and Luis Severino, but would also having Nestor Cortes and a healthy Carlos Rodon give the Yankees the edge?

This is all theoretical and there’s no telling what the standings will look like at season’s end, let alone in a week. Both the Yankees and Padres have holes to fill before they can even think about the World Series. For all we know, maybe San Diego sells high on Soto and maximizes his return before he hits free agency in 2025.

What we do know is that in a short weekend series, both the Yankees and Padres played with playoff intensity. San Diego has underachieved at the plate but the talent is there and capable of leading the team on a big run. The same goes for the Yankees, whose season was once again ravaged early by injuries.

And at the end of the day, history would probably repeat itself 25 years later. The Yankees win the World Series against a Padres team full of both talent and heart. New York’s Aaron Judge proves the difference-maker.

But the big difference would be unlike 1998, the Yankees wouldn’t win in a clean sweep. These Padres are capable of not just winning a World Series game, but competing in the series entire. The .221 team batting average is a mirage and San Diego wouldn’t just be New York’s punching bag in October.

A Yankees-Padres World Series in 2023 probably ends with the Yankees winning in six, perhaps seven. Regardless, even in defeat, San Diego would walk away with an even greater prize: New York’s eternal respect.

Josh Benjamin has been a staff writer at ESNY since 2018. He has had opinions about everything, especially the Yankees and Knicks. He co-hosts the “Bleacher Creatures” podcast and is always looking for new pieces of sports history to uncover, usually with a Yankee Tavern chicken parm sub in hand.