The Cubs are finally heading towards October baseball by clinching the playoff spot with an 8-4 win over the Pirates on Wednesday. However, the celebration did not go as expected because their elite trade acquisition, Kyle Tucker, was missing. He is nursing a calf injury, which threatens the star’s postseason effect. For the Cubs, who spent seasons rebuilding toward this moment, the timing could not be worse.
After the 2016 World Series win, the team struggled with success. They trudged through losing seasons like 2021 and 2022 before showing progress in 2023 with Dansby Swanson and Cody Bellinger. In 2024, Shota Imanaga’s addition kept the Cubs steady; however, it was the blockbuster trade for Kyle Tucker that marked their all-in push for 2025. Without him, their World Series chances are hanging in the balance.
If Tucker returns early, the Cubs might face some additional complications, though. And the reason is free agency. Spotrac projects Tucker’s market value will reach almost $498 million over 12 years, averaging more than $41 million per year. And a deal of that volume would place the former Astros star alongside only Shohei Ohtani, Juan Soto, Guerrero Jr., and Mike Trout in the $400 million club. So the question is: Will Tom Ricketts pay to keep Kyle Tucker? Or will he tighten the “velcro wallet” (as mentioned by Jon Greenberg)? As Jon Greenberg said, the Cubs’ 2026 outlook hinges on these decisions. “If Tucker is healthy and hitting, the Cubs could do almost anything,” Greenberg said, but that is a mighty big if.
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The data can say exactly how vital Tucker is for the Cubs. Despite sitting out the past two weeks, the $16.5 million star still ranks among the team’s top five hitters with a .270 BA, .853 OPS, 22 home runs, 25 SB, and 73 RBIs. Such a mixture of power, speed, and run is almost impossible to replicate. Without Tucker in the lineup, the team’s offense largely relies on Pete Crow-Armstrong and Nico Hoerner, and it can make their October path far more fragile.
But if not Tucker, then who?
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The Phillies are anticipated to trade Nick Castellanos this offseason, with reports of Bob Nightengale indicating they could also cover part of the star’s salary. BALLCAP Sports’ Jim Riley linked the Cubs as a powerful suitor, either to plug Castellanos in as a DH or as insurance if Tucker departs in free agency. However, Tucker has lifted the team all season, and Castellanos can not replace him. Either way, the Cubs’ playoff berth is only part of the story, and the real battle for the team’s future will rely on Ricketts’ willingness to match the game’s financial heavyweights.
However, the Cubs could not be the only stage for this high-stakes drama, because another powerhouse team could soon enter the mix for Kyle Tucker.
Yankees eye Tucker as Judge’s perfect partner in a dream duo
The Yankees could change the whole free-agent landscape if they join the sprint for Tucker. Imagine pairing Aaron Judge’s towering right-handed power with Tucker’s smooth lefty swing in Yankee Stadium, with a relatively short right-field fence, suitable for left-handed hitters. Analysts such as Jim Riley argue it could recreate the fearsome “one-two punch” the franchise lost when Juan Soto moved on.
For a franchise forever hungry for star power, Tucker checks every box: An elite bat, a Gold Glove in the outfield, and the kind of postseason experience the Bronx faithful needed.
Of course, it would not come cheaply. Kyle Tucker’s projected 10-year, $391.5 million deal means the Yankees would have to plunge into luxury-tax waters, something Hal Steinbrenner has cautiously balanced in recent years. But if there is one market and one brand built to absorb a megadeal, it is New York. With the Dodgers lying in wait as the formidable competition, the Yankees must decide whether Tucker is the piece that lifts them from contenders to a juggernaut.
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Kyle Tucker’s future is shaping up to be one of the defining storylines of the offseason. For the Cubs, his health and free agency will mandate whether this October sprint sparks a true window of contention or falls away too quickly. For the Yankees, his bat could reinstall the thunder alongside Aaron Judge and reshape the AL hierarchy. Either way, Tucker’s decision is bigger than one player; it is about which clubhouse is willing to push all-in.
Stay tuned, because this showdown could change baseball’s balance of power.