In a move that could prompt the Yankees to open their checkbook wider than ever, a certain Cubs star has emerged as one of the hottest commodities in the trade market. While Chicago Cubs fans cling to the hope of keeping him, it’s looking increasingly likely that a bidding war will break out—one that may just see the Bronx Bombers stepping up to make their boldest splash yet. Let’s just say, it could be the Cubs’ loss and the Yankees’ gain.

Cubs fans don’t want it to happen, but it is looking more and more likely that the Yankees will land Kyle Tucker in the 2026 offseason. The Cubs signed him for a one-year, $16.5 million deal and and given his strong start, they’ll undoubtedly want to extend his stay in Chicago.

In a recent article by John Griswold, he quoted top MLB journalist Adam Weinrib. He wrote, “He (Kyle Tucker) will ask for $500 million in free agency.” A price only a few teams, including the New York Yankees, can match.

The Yankees might look to replace Giancarlo Stanton after the 2027 season, and Tucker might be the perfect fit. The two of them had almost identical stats last season, but Tucker achieved similar stats despite playing only 79 games. Another reason why this deal might come in handy to the Yankees is because of their financial flexibility.

They have an opt-out clause with Gerrit Cole and with some other players not performing. This means Brian Cashman and the Yankees might open the door for Tucker to come into the Yankees clubhouse. If this blockbuster signing happens, Tucker would become only the fourth MLB player to secure a $500+ million deal.

If the Yankees do open that door, don’t be surprised if they roll out a red carpet made of hundred-dollar bills. With Stanton’s timeline winding down and the Bronx faithful hungry for the next superstar, Tucker may be less of a luxury and more of a necessity. After all, when the Yankees see a lefty slugger with MVP upside, restraint usually isn’t part of the playbook.

Why extending Kyle Tucker could define the Cubs’ next era

At some point, a franchise has to decide whether it wants to flirt with greatness or commit to it. The Cubs, flush with payroll flexibility and finally showing signs of life beyond mediocrity, are standing at that crossroads—again. This isn’t about sentimental reunions or bargain-bin pickups. It’s about making a statement. Here’s why extending Tucker isn’t just smart—it might be non-negotiable.

The first mistake the Cubs made was signing Tucker only for a year, but if they fail to act now, they risk making another costly mistake. After the 2026 season, Tucker’s contract is up, and teams are waiting in line to sign him, and the Cubs are also one of those teams. This is the best time for the Cubs to sign Tucker because, in free agency, you will not be the only team in the race.

With the way Tucker has started the season, the Cubs are looking dangerous. He has a batting average of .328 with 5 home runs and 18 RBIs. Not only that, in 2024 he played just 78 games, but he had very good numbers with 23 home runs. When asked about his time with the Cubs, Tucker remarked, “It’s been great ever since I’ve been over here… I’m just here to play some baseball and see what happens after that.”

If that sounds like the kind of player you let walk, then maybe you deserve to keep chasing .500 forever. The Cubs have the money, the momentum, and a golden opportunity staring them in the face. Extending Tucker isn’t a luxury—it’s a litmus test. Pay the man, or prepare to watch him mash against you for the next decade. Your move, Chicago.