The most seasons the Yankees have gone in more than a century without making it to the World Series is 14. They went that long after making it to the 1981 World Series, and have just done it, in real time, after making their last Series in 2009. For the Yankees, there will always be World Series pressure simply because they’re the Yankees and have already made it to the Fall Classic 40 times in their history. But there is a heightened urgency going into the ’24 season, one that involves their two biggest stars, Aaron Judge and Gerrit Cole.

This is how a Yankees fan as informed and passionate as I know put it to me the other day:

“My greatest fear is that we’re going to play through [Judge’s and Cole’s] primes without making it back. It’s why they had to go after [Juan] Soto, even if they only have him for this season. They couldn’t kick the can down the road. They had to go for it right now.”

Judge and Cole are their two stars, in whom the Yankees have invested nearly $700 million. Everybody knows why. The season before last, Judge broke the American League record for home runs in a season when he hit 62. He passed Babe Ruth and he passed Roger Maris, and gave Yankees fans a September they will remember forever. In the process, he became the most popular -- and homegrown -- Yankee since Derek Jeter. Now he’s the captain the way Jeter was.

Cole has become the truest and best Yankees ace since CC Sabathia, along with being everything they could have hoped he would be across his first four seasons in pinstripes. Cole just capped that off by winning his first Cy Young Award. At his best, he has been the kind of right-handed power pitcher Roger Clemens was in the Bronx.

By the time Cole pitches through the 2024 season, he will be more than halfway through the nine-year contract he signed after the '19 campaign. He will also turn 34 before the upcoming season is over. Judge will turn 32 in April, as he enters just the second year of his nine-year contract. They are, as my friend noted, both very much in their baseball primes.

Cole was as dazzling a pitcher last season as he was in 2019, when he could easily have won his first Cy Young with the Astros, a season he finished 20-5 with a 2.50 ERA (he went 15-4 for the Yankees in ’23 with a 2.63 ERA). And Judge? Even missing 56 games last season with a right big toe injury he sustained running into a door in the outfield at Dodger Stadium, he hit 37 home runs. If Judge had played the same 157 games he had the season before, the numbers indicate he would have gone for 50 home runs or more.

Cole has played in the World Series once, for the Astros, in 2019, with Houston losing to the Nationals in seven games despite having been ahead three games to two. But Judge still hasn’t made the Series, losing three American League Championship Series, all against the Astros. The closest Judge came in those was a Game 7 in '17.

The Dodgers, of course, will be under tremendous pressure to make it back to the Series for the first time since 2020 after they signed Shohei Ohtani and Yoshinobu Yamamoto as free agents. They also signed Teoscar Hernández and James Paxton as free agents and traded for Tyler Glasnow. And they might not be done yet.

You know the Braves, another powerhouse over the past few seasons, will be highly motivated to get back to the World Series after being upset by the Phillies in the past two Octobers. The Dodgers and Braves have great players, too, who are also in their primes. The Dodgers already had Mookie Betts and Freddie Freeman before they signed Ohtani. And the Rangers want to become the first team since the 1999-2000 Yankees to repeat as world champs. By the time the Astros get to Spring Training, they will have had four months to think about losing Game 7 of the ALCS to the Rangers.

The difference is that the Dodgers, Braves and Astros won their divisions in 2023, and the Rangers came as close as you can come. The Yankees didn’t come close, finishing fourth in the AL East. One other point: Those first three teams have won the past four World Series.

The Yankees, as they’re regularly reminded, haven’t been to the Fall Classic since the decade before last.

“We’ve had great pitchers in and out of this place, leaders on and off the field,” Cole said when he won his Cy Young. “Those are people who set a really high example and a really high bar of what it means to be a great Yankee. That served as an inspiration to me as a kid, and now, I’m living out my dream.”

Cole was a Yankees fan as a kid, back when Joe Torre’s Yankees were winning four World Series in five years. So, he knows full well what the dream is at Yankee Stadium. Cole wears the uniform now. He wants to win one there. So does Judge. It’s not just the Yankees who are on the clock. They are, too.