Jed Hoyer talks potential Kyle Tucker extension timeline, Cubs' trade deadline plans

Although the Chicago Cubs are rolling right now at 41-26 and a return to the postseason is looking more likely by the day, the impending free agency of their superstar right fielder still looms. Kyle Tucker has been a consistent point of discussion throughout the season as fans have hoped that, somehow, Jed Hoyer and company can find a way to keep him around beyond 2025. Currently with a slash line of .279/.392/.520, a wRC+ of 155, and a track record of star-level success at the plate, he'll command a contract galaxies beyond what the team has had the appetite for in the past.

There has been no shortage of rumors about talks and discourse from MLB executives and beyond over the Cubs' ability to get a deal like this done. As one of the most valuable teams in the sport, they should have the resources to give Tucker the megadeal he'll seek. Alas, in a walk year where he's going to be by far the biggest name on the market, there's little incentive for the outfielder to accept an offer in-season unless it's a no-brainer. Vladimir Guerrero Jr.'s $500 million extension also raised the bar further. Still, they have to try, and Hoyer just gave an idea of when they could take that shot.

In a recent appearance on Jon Heyman and Joel Sherman's The Show podcast, Hoyer was asked about the status of Tucker in a Cubs uniform. Beyond highlighting all the good the superstar has brought to the lineup, he largely stuck to the same line about keeping conversations internal and recognized the "options" he'll have. If you were hoping for a mid-season extension, though, don't hold your breath, as he heavily indicates that the goal is to let Tucker play and fall in love with the Cubs before making their pitch at the end of the year.

"Obviously, we gave up a lot to get him, and you know we’d love to keep him long term," he told Heyman and Sherman. "As far as conversations go, I keep that in house, but certainly he's a player who's going to have options at the end of the year, but we'd love to love to keep him and hopefully the best sales pitch you can have is a winning team and an awesome place to play and, so that'd be the hope."

Notably, Hoyer doesn't entirely rule out mid-season extension talks, say, at the All-Star break, but he reiterated that, "if we were having discussions, I wouldn't talk about it, but I think the likelihood with any player is that deals get to the end of the year. So I was sort of saying that as the assumption that, for the most part, contracts that aren't to really young players get signed at the end of the year."

More than likely, serious discussions will wait until after the Cubs are done playing and just days before free agency, where deep-pocketed teams like the Dodgers and Yankees will be waiting.

Jed Hoyer outlines the Cubs' biggest trade deadline needs

In the more immediate future, Hoyer has to consider what deals to make to improve the 2025 team. With Tucker feeling more and more like a one-and-done player for the Cubs, they need to capitalize on the unexpected success they've had this year. Hoyer seemed to understand that, even if he still plans to be a bit opportunistic looking for "the right transaction that makes sense to push in." There's still a concern about not mortgaging the future, but the reports of the team being very active looking for improvements are true. They might not, however, be jumping to make any moves just yet, though.

"Every year, sustained success is obviously the goal for every team, but you also have to be humble enough to realize like sometimes teams come together really well and sometimes they don't," he continued. "I think that… six weeks from now, if we're at the deadline and things are going well, you have to always evaluate those seasons when things are going well."

Hoyer also confirmed that "pitching is the likely direction that we would take if we're adding." The starting rotation is the obvious candidate with Justin Steele out for the season and the lack of an obvious frontline arm. However, he emphasized that they'll always be on the lookout for relievers because of how volatile bullpens are.

The Cubs are on a good run right now, with a mix of young arms and reclamation pieces, including Daniel Palencia, Brad Keller, Drew Pomeranz, Chris Flexen, and Caleb Thielbar, all having ERAs no higher than 2.05, but they could use another back-end arm with swing-and-miss stuff. Whatever the case, they don't plan on standing pat because of recent success.