The Chicago Cubs are confronting a significant decision as the 2025 season draws to a close. After acquiring outfielder Kyle Tucker in the offseason, the star is set to become a free agent this winter. With Tucker performing at a high level for the Cubs, the team must decide whether to invest heavily to ensure their outfield future remains secure.
On a recent broadcast of 670 The Score, ESPN’s Jeff Passan discussed Tucker’s impending free agency and the likelihood of the Cubs retaining him amid competitive interest from other teams.
Projected Contract Demands and Cubs’ Outlook
When asked about the potential contract value Kyle Tucker might command on the open market, Passan estimated,
“I think the over under is $450 million,”
indicating the magnitude of the financial commitment required. Despite concerns about bidding wars among teams, Passan affirmed that Chicago remains the frontrunner to sign Tucker.
This assessment comes amid ongoing debate during the season about whether the Cubs are prepared to meet the high price tag or if they risk losing Tucker to other suitors. Passan maintains the Cubs’ advantage but highlights the complexity of the team’s outfield roster, which includes promising prospects who could influence decisions.
The Cubs’ Outfield Depth and Internal Competition
Passan pointed out that the Cubs have plenty of talent vying for outfield roles.
“They see what he’s done, but I’ll tell you what guys, Owen Caissie is still sitting at Triple-A right now,”
he said, adding that Caissie
“would look pretty good in right field.”
This emphasizes the depth of Chicago’s outfield options beyond Tucker.
Cubs president of baseball operations Jed Hoyer echoed this sentiment earlier by stating,
“there’s no reason we can’t have both, Owen Caissie and Kyle Tucker,”
suggesting the organization envisions a future featuring both players, despite the limited outfield positions available.
Currently, the Cubs have Ian Happ, Seiya Suzuki, Pete Crow-Armstrong, Kyle Tucker, and Owen Caissie competing for only three outfield spots, creating a surplus that fuels speculation about the club’s strategy for the trade deadline and offseason.
Trade Deadline Moves and Strategic Conservatism
This crowded outfield influenced fans’ expectations that the Cubs might trade from this surplus to strengthen areas elsewhere and push for a World Series title. Passan commented on the Cubs’ approach at the trade deadline, saying,
“I think that’s why Cubs fans are disappointed. It felt like there was room to deal from a surplus to go win this World Series.”
He further reflected on the cautious nature of the Cubs and Red Sox at the deadline:
“If the Cubs and the Red Sox similarly, can be accused of anything, it’s being a little too conservative at this deadline. But man, paying prices at the deadline, it’s a really hard thing for teams that try to make good decisions to do because deadlines are irrational, and they create irrational behavior.”
This conservatism, particularly in dealing potential outfield assets like Caissie, may signal Chicago’s intent to retain their current core and not reshuffle the outfield drastically midseason.
Balancing Talent and Commitment Ahead of Free Agency
Supporters argue the best move for the Cubs involves locking in Kyle Tucker’s services this winter. Twitter user Cody Delmendo emphasized this view, writing,
“For all of this to make sense, the only way at least for me, is to just pay Kyle Tucker this winter. Once that is done they at least have him and PCA for multiple years with young talent they probably want here and plenty of assets on the major league and minors roster to move.…”
—Cody Delmendo, Twitter
The Cubs’ failure to trade Owen Caissie for starting pitching at the deadline suggested they may be counting on both Caissie and Tucker in the near future. Passan, however, doubts Caissie alone will assume the right-field spot and believes the company of both outfielders is possible.
The Cubs’ World Series Hopes and Future Outlook
While the Cubs hold an All-Star outfielder in Tucker for the remainder of the season, their goal is to leverage recent trade deadline additions to shore up roster weaknesses and mount a serious World Series challenge for the first time since 2016.
The ultimate test will be whether their moves can carry them deep into October, while the decisions made this offseason over Kyle Tucker’s contract will have lasting implications. Committing large resources to keep Tucker appears essential for Chicago to secure a competitive and talented outfield in the coming years.