After finishing a strong regular season with a 92-70 record and winning their first playoff series since 2017, the Chicago Cubs’ season ended in a five-game NLDS loss to the Brewers. And since they are out of baseball, all the attention moves towards the team’s outfielder Kyle Tucker’s free agency, who came to Chicago from the Astros in return for Isaac Paredes, Hayden Wesneski, and Cam Smith.

Jordan Campbell of Cubbies Crib recently analyzed the situation where Tucker’s awkward exit from Chicago seems certain. Campbell pointed, “Kyle Tucker’s thank you to Chicago Cubs fans and Jed Hoyer’s end-of-season remarks didn’t directly confirm that the two sides were going to go in separate directions this offseason, but that was the takeaway most had.”

After the Cubs’ elimination in Game 5 of the NLDS, Tucker posted several photos of his Chicago tenure with a heartfelt caption that reads: “Thank you Chicago for riding with us all year long! Y’all’s support was there no matter what, and we couldn’t have done it without you.#FlyTheW🐻.” This message sounded like a final goodbye.

And though the Team president said that, “obviously now, we’re into free agency and … we’ll be having those conversations. Like I said a bunch of times during the season, everyone could use a guy like Kyle Tucker. Everyone gets better by having a player like that. We’ll certainly be having those conversations,” seeing the club for years and what Tucker’s contract can be, When fans hear that the Cubs will ‘have conversations’, it’s hard to think they will go on to sign the player.

Plus, the Cubs hoped a year in Chicago would be a great selling point, but the thought may have backfired as Wrigley Field has leaned heavily toward being pitcher-friendly recently, and that can make Tucker “want to play his games elsewhere.” And beyond the ballpark, there is another huge issue.

Campbell pointed out, “Looking beyond circumstances on the field, it would also seem that the Cubs are shying away from financial commitments beyond the 2026 season. The looming work stoppage for the 2027 teams has teams cautious in terms of what spending and payroll look like with a new collective bargaining agreement.”

So, the Cubs seem likely not to want to be stuck with massive contracts under a new, unknown CBA and would “likely have interest” in a short-term deal. But it won’t eventually work out, as Campbell notes that Tucker has no reason to take it, since the teams “like the Los Angeles Dodgers, Philadelphia Phillies, [and] New York Yankees” are looming. These big-market clubs will offer the 10-year deal. The Cubs “will be priced out of the sweepstakes.”

But here’s a catch. If the Cubs “were told at the start of the 2025 season that it would only cost $350MM to ensure Tucker remained with them for the next decade, they would have jumped at that opportunity,” as per the report.

Then what happened suddenly? Tucker, who was almost an MVP candidate for the first three months, and was expected to land on a $500M contract after Juan Soto, Shohei Ohtani, and Vladimir Guerrero Jr., missed most of September with a left calf strain and struggled most of the second half of the season. He finished his season with a career low of 22 homers and 73 RBI.

Still, the New York Yankees, who recently lost Juan Soto last winter, can go all out to fill that offensive gap and left-handed bat in the lineup. They also have openings as Cody Bellinger and Trent Grisham hit free agency.

The Yankees will surely be at the top of the table, but they’re not the only ones

The richest team in baseball might have the most interest in the outfielder. MLB insider Jon Heyman reports the Dodgers are “expected to make a play” for Tucker. He says, “Dodgers people are said to love Tucker, and the outfield is their one area of less than great strength. While their payroll is already an MLB-record $400M, they did try for last year’s No. 1 free agent, Juan Soto, with an offer of about $600M (with deferrals, of course) before bowing out and finishing fifth among five finalists in the biggest free agent derby ever. ”

Plus, they could put Tucker in right field in the place of Teoscar Hernández while moving him to the left, which will make their super-team even stronger.

And if the Dodgers somehow fail, other teams like the Philadelphia Phillies, the New York Mets, and the Boston Red Sox always have money to spend in the outfield. And the Toronto Blue Jays, who are coming off a World Series run, could make a splash.

For now, we don’t know where the King Tuck is going to land for the 2026 season or what his contract value is going to be. But the looming 2027 work stoppage is a real concern, and that looms over every single negotiation for the upcoming free agency.