What once felt like a magical season for the Chicago Cubs is now on the brink of disaster. Their 7-3 loss in Game 2 of the NLDS against the Milwaukee Brewers put them in a 2-0 hole in the best-of-five series. They're still alive, but will have to win three games in a row against the team that finished the regular season with the best record in the majors to advance beyond the NLDS.
Somehow, the Game 2 loss wasn't the most frustrating and anxiety-provoking bit of news that came out on Monday night in the eyes of many Cubs fans. When asked about the odds that the Cubs re-sign Kyle Tucker, a free agent to be, this offseason, ESPN's Jesse Rogers casually revealed that Tucker is a goner. He definitively stated that he will not be back in 2026, and that the Cubs were never going to re-sign him.
No. They were never going to. Anyone that said different was wrong.
— Jesse Rogers (@JesseRogersESPN) October 7, 2025
There's no definitive answer as to whether this is simply Rogers' opinion or if it is sourced, but Rogers is a plugged-in Cubs beat writer, so there's no reason to believe he's wrong here.
Most Cubs fans had come to terms with the idea that Tucker was going to be one-and-done in Chicago, as his price tag is expected to soar well over the $300 million mark. The tone in which Rogers uses, though, making it abundantly clear that the Cubs were never going to even entertain the thought of extending Tucker, feels like a slap in the face to Cubs fans.
For more news and rumors, check out MLB Insider Robert Murray’s work on The Baseball Insiders podcast, subscribe to The Moonshot, our weekly MLB newsletter, and join the discord to get the inside scoop during the MLB season.
Why Kyle Tucker already has one foot out the Cubs door
This comes down to money. Tucker hasn't had the second half or postseason Cubs fans hoped for when the team acquired him, but he was still worth 4.5 fWAR during the regular season and has undoubtedly elevated this Cubs team. He was one of the game's best players entering the year, and while he hasn't been quite as consistent as expected, he had another great year in 2025.
Tucker is going to be the highest-paid free agent by a wide margin, and while he won't get Juan Soto money, he's going to get upwards of $300 million. For a Cubs team that has never shelled out a contract larger than Jason Heyward's eight-year, $184 million pact signed in the 2015 offseason, the odds of them jumping from there to where Tucker will land have never been all that great. I mean, Dansby Swanson is the only nine-figure contract the Cubs have handed out in the past seven years.
Owner Tom Ricketts has been frugal, and the same can be said about the head of baseball operations, Jed Hoyer. It'd be against everything the Cubs have done to re-sign him, as insane as that is to say out loud.
Tucker could love it in Chicago, but he's not going to sacrifice hundreds of millions to stay there, and it's hard to blame him.
Cubs ultimate goal of Kyle Tucker trade couldn't be clearer now
Knowing that it will almost certainly be a one-and-done for Tucker in Chicago with little resistance from the Cubs to change that, it's now abundantly clear that the goal of the Tucker trade was not to win the World Series, it was to get back to the postseason.
who said anything about winning the WS? They haven't made the postseason since 2018. That was the goal. Then its hope for the best. If they build up a good team for several years, they'll prob make that big deadline deal that helps for WS and not just playoffs.
— Jesse Rogers (@JesseRogersESPN) October 7, 2025
The Cubs won the World Series in 2016, but they hadn't made the postseason before getting in this season since the shortened 2020 season. They hadn't made it to the postseason in a full season with fans since they lost the NL Wild Card Game in 2018. They hadn't won a playoff game since they made it to the NLCS in 2017. In other words, it had been a while since the Cubs had been competitive, so Tucker was brought in to change that.
Now that the Cubs got what they wanted, they seem content no matter what. They aren't eager to bring Tucker back, and they weren't eager to make any splashy moves outside of the Tucker addition.
Cubs' goal with Tucker explains lack of urgency to win now
Cubs fans thought that trading for a superstar like Tucker on an expiring contract was a win-now move, but it was a "get to the playoffs now" move. The other moves they made (and didn't make) proves that.
They made the big Tucker splash, but their other offseason additions were on roster gambles like Matthew Boyd, Colin Rea, Carson Kelly, Ryan Pressly and Justin Turner. Most of these deals ended up working and helping the Cubs out, but they refrained from making a single big move after trading for Tucker.
At the trade deadline, when the Cubs clearly needed pitching help, the Cubs refrained from trading their top prospects, instead choosing to make smaller moves for rentals like Willi Castro, Andrew Kittredge, Michael Soroka and Taylor Rogers. Again, some of these deals worked out, but how much better would the Cubs had been had they acquired a frontline starter? And yes, I know none of them were moved, but the Cubs had enough to offer to overwhelm a team like the Minnesota Twins to trade Joe Ryan.
By the time the trade deadline arrived, the Cubs were 18 games over .500 and were sitting comfortably in a postseason spot. They didn't feel the need to go all-in again when making the playoffs was likely, so they didn't.
Overall, the Cubs made moves to marginally improve without sacrificing anything in terms of future prospect capital or dollars before and after the Tucker deal. They were willing to trade a whole lot to get Tucker, but were unwilling to continue to push. That will forever define the 2025 season, assuming they fall short.
Chicago is left without a World Series path
Assuming Tucker departs and the Cubs, once again, refrain from making a major-money signing, what exactly is the plan for getting this team in the World Series conversation anytime soon?
The trade hasn't aged abysmally, but the Cubs gave up three valuable players in Isaac Paredes, Cam Smith and Hayden Wesneski, all for one year of Tucker. This left the Cubs without much left to deal, especially if they hold onto top prospects Owen Caissie and Moises Ballesteros, as they appear eager to do. Unless Caissie and Ballesteros can find a way to duplicate or top Tucker's production, how will this offense be any better? If Caissie and Ballesteros aren't going anywhere and the Cubs won't splurge on a star free agent, how are they going to meaningfully improve their rotation?
Cubs fans want more than just a Wild Card berth and an embarrassing NLDS exit at the hands of a division rival — they want a World Series. The organization's goals simply don't align, though, by willingly letting Tucker walk. I have no idea how the Cubs will compete for a title anytime soon if the organization has not shown a desire to go all-in and spend like the big market giant that they are.
Cubs' Kyle Tucker stance is a slap in the face to fans
Cubs fans are among the most loyal in all of sports. No matter how good or bad the team is, Wrigley Field is packed every single night. Some of that admittedly has to do with the experience of attending a ballgame at one of professional sports' most iconic venues, but a large chunk of that has to do with the fact that (most) Chicago fans love their Cubbies. Whether Tucker stays or leaves, nothing will change on that front.
This unrelenting loyalty is both a blessing and a curse. It's obviously great to see Wrigley Field packed to the brim every night, but the fact that the Cubs know fans will sell the place out virtually every night, no matter what, makes it so that the Cubs don't have to be quite as desperate to win the World Series. Why else would they have made the deal they did for one year of a player they knew wouldn't be back?
I'm not a Cubs fan and I don't live in Chicago, but if I did, I'd be pretty irate right now. Sure, the team got back to the postseason, but at this point, who cares? They beat a flawed San Diego Padres team in the Wild Card Series and are now getting obliterated by their division rivals in the NLDS. Not only are the Brewers their NL Central rivals, but they're the team that used to employ Craig Counsell, and they're an organization that spends almost nothing when compared to the Cubs. Shouldn't this proud franchise be aiming higher?
By trading for Tucker, the Cubs organization got fans to buy in and expect them to go all-in on a World Series title. In reality, Cubs fans got duped — it's that simple. The Cubs traded for a superstar with no plans on re-signing him and then failed to add necessary pieces around him to seriously compete for a World Series title.
Cubs fans deserve so much more than what they have gotten in recent years, and this Tucker situation is proof of that.
Kyle Tucker reality is tough for fans to accept
Losing a bidding war for Tucker would've stung, but Cubs fans could've at least known that the organization was taking bringing him back seriously. At the end of the day, it's a two-way street, and the Cubs can't force Tucker to re-sign, even if they put up a valiant effort. What's harder to accept is the seeming acceptance that the Cubs won't even be involved.
The Cubs are one of the most valuable teams not only in MLB, but in all of sports. They have resources up the wazoo, with the ability to pay just about anyone and not break a sweat. The Cubs staying out of bidding wars for superstars like Soto and Shohei Ohtani in recent years has been frustrating, but at least those players weren't in Chicago originally. Tucker is a superstar who spent a year in Chicago, so it's harder to accept that the Cubs will not even try to bring him back when they were willing to trade for him and not even take winning a World Series with him seriously.
New York Yankees fans weren't happy when Juan Soto left the Bronx after just one year with the franchise, but at least the organization did what it could to win and keep him in town. It didn't work, but the attempt was there. This Cubs situation doesn't match that. They did not go all-in on a World Series in their only guaranteed year with Tucker, and they're not going to do whatever they can to re-sign him.
This whole situation is a tough one to accept. The Cubs didn't go all-in despite selling that vision, and nothing suggests they're going to do so anytime soon. They made it to the playoffs, but that doesn't feel as exciting knowing how the season is likely going to end. I fear nothing will change in the near future, and that, again, is a shame.