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The ALDS-bound New York Yankees await an answer to a simple question: Cleveland or Tampa Bay?

It’s not just another tale of two cities, each with their respective teams. The Guardians and the Rays each have storied rivalries with the Yankees and are each fighting to advance in the playoffs. Their best-of-three AL Wild Card series kicks off Friday in Cleveland, with the winner headed to Yankee Stadium for Game 1 of the ALDS on Oct. 11.

The Yankees, in turn, know both teams well. The Rays are a worthy AL East rival who eliminated New York in the 2020 ALDS en route to the World Series. In the preceding Wild Card Series, however, the Yankees dispatched the then-Cleveland Indians handily.

Not to mention, Cleveland and New York’s playoff history goes back almost two decades. With the new-look Guardians and feisty Rays, anything can happen.

But who would the Yankees rather face?

Pros for the Guardians. The best thing about facing the Guardians is that the AL Central is, in a word, terrible. Cleveland took baseball’s weakest division with a modest 92-70 record thanks to the White Sox underachieving and the Twins’ second-half collapse. Now, they face a Yankees team that won 99 games and certainly would have won over 100 if not for an August slump.

New York also handily won the season series against Cleveland, including a three-game sweep in the Bronx. With home-field advantage for the ALDS, facing the Guardians again is an inviting possibility.

Cons for the Guardians. Yet, weak division aside, Cleveland is a good-hitting team and ranked seventh in MLB with a .254 team batting average. Team star Jose Ramirez was at the forefront of this, leading the Guardians with 29 home runs and 126 RBI. Andres Gimenez also hit 17 homers in a career year. Let’s not forget that Cleveland has a Top-10 pitching staff led by former Cy Young-winner Shane Bieber, and star closer Emmanuel Clase is a deadly bullpen arm.

History might also be on the Guardians’ side in this case. This postseason marks the 25-year anniversary of then-AL Central champ Cleveland forcing an ALDS Game 5 behind Sandy Alomar Jr.’s walk-off home run. The Yankees were eliminated the next day and Cleveland went on to lose the World Series.

It doesn’t matter that the Yankees have won three of four playoff series against Cleveland since 1997. Sometimes, history just finds a way to repeat itself.

Pros for the Rays. Tampa Bay has long been a thorn in the Yankees’ side, but this year’s team seems different. Kevin Cash’s dependence on young pitching saw the Rays finish fourth with a team ERA of 3.41, but that foundation is breaking down. Shane McClanahan came back quickly from a shoulder impingement in September, Corey Kluber is old, and Tyler Glasnow just came back from Tommy John surgery.

The Rays also got banged up at the wrong time, and badly. Several important relief pitchers are currently on the injured list, meaning Cash’s unique bullpen creativity will be tested. The hungry Yankees won the season series, so look for the lineup to be just as aggressive as Tampa Bay’s.

Cons for the Rays. Even the best teams have a rival that just gives them fits. For years, the Rays have been just that for the Yankees. Be it simply underachieving or something else, New York has had its hands full with Tampa Bay more recently.

Thus, with the Rays banged up, the worst thing the Yankees can do is underachieve in the ALDS. Assuming Tampa Bay beats Cleveland, Cash is a good enough manager to rally his troops and have them embrace their status as underdogs. If the Rays’ pitchers show up and are on, New York could easily backslide into old habits. Instead of being aggressive and establishing baserunners, the worst thing they can do is wait for the Rays to make a mistake.

The 2020 demons and Mike Brosseau’s home run still sting a bit. Hopefully, not bad enough that the Yankees anxiously swing their way toward an early exit again.

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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.