The Chicago Cubs are maybe in two boats about the situation that’s come about with Kyle Tucker. They, for one, knew what they were signing up for when they made that deal with Houston to get Tucker to Wrigley. The Cubs officially acquired Tucker from the Houston Astros on Dec. 13, 2024, in a trade that sent Isaac Paredes, right-hander Hayden Wesneski, and prospect Cam Smith to Houston. One doesn’t go out to get one of the best all-around players without knowing that the price tag to retain him will be steep. Still, the decision seems a lot like the New York Mets’ gamble over Pete Alonso.

Polar Bear is a franchise-defining star that the Mets got. However, he will be entering free agency, and talks about him leaving have already started. Not to get started that Scott Boras is behind him. And it’s the same way for Chicago, given Tucker is set to become a free agent this winter. Both situations expose teams to short-term solutions that could cost them long-term payroll flexibility if the player re-tests the market. But for Chicago, the biggest problem is that right now, Tucker is not the player they laid all their cards out for.

Since July, Tucker has batted a rough .195 with only one home run. Cubs fans are already frustrated and let Tucker know by recently booing him after his lackluster at-bat against Pittsburgh. Multiple game recaps and local reports documented boos and a visible negative reaction during a recent game; the episode was widely shared on social platforms. Even worse is that Tucker didn’t hustle a routine grounder, which just added more fuel to the fire. Sure, Chicago managed a 4-3 in the game, but Tucker’s slump has been looming large. And it’s not just the fanbase that’s reacting or overreacting!

Patrick Mooney from The Athletic best put it, “The clock is ticking on Tucker’s time in Chicago, where the size of his next contract is no longer a constant topic of speculation. The Cubs stomached the cost to acquire Tucker in a blockbuster trade with the Houston Astros last offseason, knowing that he would become a free agent and sign with the highest bidder.” That’s the risk the Cubs took, much like the Mets with Alonso. New York gave a short-term deal to Alonso with an opt-out after Year 1. But of course, the front office plan is already being questioned.

Chicago could be down the same road with Tucker, given the early estimates of his next deal are looking north of $600 million. On the surface, Tucker’s numbers look elite. A .265 average, 18 homers, 62 RBIs, and 25 steals, plus he also trails behind just Pete Crow-Armstrong in WAR among the Chicago Cubs position players. But look at his second-half slide—a .198 average since the break. So, of course, are the Cubs about to shell out a billion dollars for a player who has not even won over the club yet?

Jed Hoyer did mention that the team is in an enviable position and that Tucker is one piece that a team keeps “long-term”. That might be true, given Tucker’s history, but for now, he needs to flip the switch. Both for him to get the best out of the free agency and for the team that took a gamble on him. The Cubs’ front office now faces a classic options problem — extend early and risk overpaying after one hot season, or wait and risk losing the player or overpaying after another arbitration-style negotiation — and that tradeoff is at the heart of the club’s next moves. And as far as Pete Alonso goes, it seems like he might just be ready to test free-agency waters again.

Pete Alonso’s likely headed back to free agency

Pete Alonso may have signed a two-year deal with the New York Mets, but currently, it’s looking more like a pit stop. He had a down year in 2024, and he didn’t get a long-term deal. He settled for a short-term one. But fast forward to now, and he is having one of the best years of his career. The All-Star honor, big numbers at the plate, and he recently became the Mets’ all-time home run leader! And that says something about how his value has rocketed. Athletic put Alonso in the Top 25 players likely to hit free agency.

CBS Sports’ Mike Axisa didn’t mince words and even predicted Alonso’s next move. “Alonso can opt out of a $24 million salary for 2026, and he will do that barring injury… Alonso will head back into free agency and hope to secure the long-term deal he was unable to land this past offseason.” And it’s hard to argue with that logic, right? He, after all, has shown his power and reminded everyone why he is one of the most feared bats in the game. The Mets could have locked him for longer, but they didn’t, and it can bite their budget.

Jim Bowden also agreed and mentioned that Pete Alonso will most likely be looking for a long-term commitment next. “If they don’t [extend him], I believe this time around he won’t be as open to signing another short-term contract and will instead go to a team that’s willing to offer him a long-term commitment.” So at this point, the math is simple: Alonso has outperformed his contract; hence, he could demand twelve years north of $100 million. It remains to be seen if New York will make the home run king walk away.