This probably comes as very little comfort to fans of the Chicago Cubs, but the majority of executives in Major League Baseball agree with you:
Kyle Tucker will test free agency after the end of the 2025 season.
In an unofficial poll conducted by MLB.com, most front office representatives from around the league stated they feel it is extremely unlikely that Tucker will sign an extension during the season to remain with the Cubs. While noting that Vladimir Guerrero Jr., who was also scheduled to hit free agency during the offseason, recently signed a 14-year, $500 million contract to stay with Toronto, the industry insiders said Tucker is certain to wait and see how much his skills are worth.
“He’s likely to be the best player on the market by a decent margin; I can’t imagine him giving up the opportunity for a bidding war to potentially take place for his services,” one National League executive said.
Jed Hoyer, Carter Hawkins Could Forever Regret Trading for Kyle Tucker
But there is one significant difference between the two scenarios. Guerrero had played his entire career with the Blue Jays, but the Cubs just acquired Tucker from Houston in December for Isaac Paredes, Hayden Wesneski and Cam Smith.
So while the Toronto front office indeed felt pressure from the fan base to keep its homegrown superstar, Chicago president of baseball operations Jed Hoyer and general manager Carter Hawkins know that their careers will likely be directly impacted by what happens – or doesn’t happen – with Tucker.
“It’s extremely important this front office does everything they can to try to sign Kyle Tucker as soon as possible and not let him get to free agency,” MLB analyst Jim Bowden said on the “Foul Territory” podcast. “Because if you let him get to free agency and lose him after trading Cam Smith to get him, you know, that’s one of those deals you’ll regret the rest of your career.”
And that pressure, Bowden said, can help explain why the Cubs demoted rookie third baseman Matt Shaw so early in the season. The 23-year-old had certainly struggled, getting just 10 hits and 10 walks against 18 strikeouts over 58 at bats, but Bowden was critical of Chicago potentially damaging Shaw’s confidence.
“For him to make the team out of spring training, obviously it was a mistake, because I don’t like sending a guy out after 20 games of failure, I don’t think it’s fair,” Bowden said.
“I don’t think you send Matt Shaw down if you don’t feel that sense of urgency from ownership. You haven’t been extended, your contracts are up. You feel the pressure. And by the way, I picked the Cubs to win this division, so I think they’re gonna be able to keep their jobs. But I do think when you see moves like they’re making this quickly out of the gate when they don’t need to, I think it tells you the sense of urgency, as the Tucker deal did.”
MLB Analyst Believes Cubs Will Make Trades to Win With Kyle Tucker
Bowden also stated that, particularly with the loss of Justin Steele for the entire season, he believes the Cubs will make a trade for one of the top available starting pitchers.
“It’s win or get fired, right? Jed Hoyer knows that, Carter Hawkins knows that. It’s why they made the Kyle Tucker deal,” Bowden said. “You don’t make the Kyle Tucker trade if you think you’re going to be there long term. You do not give up six years of Cam Smith for what appears to be one year of Kyle Tucker. So you have to do everything you can to win right now.”
Cubs Execs Show Signs of Pressure Amid ‘Win Now or You’re Fired’ Scenario