Cubs selling at trade deadline could pay blockbuster dividends in offseason

No team in the National League has disappointed more than the Chicago Cubs. The expectation was, after re-signing Cody Bellinger while bringing in Shota Imanaga and Craig Counsell that a Cubs team that narrowly missed the postseason in 2023, to make the playoffs, but barring a miracle, that's not going to happen.

With the Cubs losing two of three against the Brewers, they are now 49-55, 5.0 games back of the third Wild Card spot. That might not sound like too big of a gap, but FanGraphs gives them just a 5.8 percent chance of making it to the postseason thanks in large part to the number of teams in front of them.

Those slim odds have made it almost a certainty that the Cubs will be selling with the trade deadline coming up. As frustrating as it is that Chicago is in this position, it could wind up paying dividends for them as soon as the offseason for reasons some might not expect.

(For more news and rumors, check out MLB Insider Robert Murray’s work onThe Baseball Insiders, and join the discord to get the inside scoop as we near the July 30 MLB trade deadline.)

Cubs selling at trade deadline opens the door to massive blockbuster opportunity

The Cubs won't be involved in trade talks for some of the best available players at this year's deadline, but that doesn't mean they'll also be waving the white flag in 2025. The Cubs understand where they are right now and are willing to part with some rentals, but they fully intend on competing in 2025 and will be looking to add as soon as this offseason, potentially in a trade, according to Ken Rosenthal of The Athletic.

Garrett Crochet's name has been a popular one in deadline talks, and he might get dealt, but there are reasons to believe that the offseason is the best time for the Chicago White Sox to trade him.

"At the moment, the teams with the most interest in Crochet are contenders. The list of suitors could expand in the offseason to include teams currently out of contention, but planning to compete in 2025. The Chicago Cubs, for example. The Blue Jays. Perhaps even the Nationals," Rosenthal wrote.

There's an expansive list of contenders interested in Crochet now, but some teams that won't be looking to buy now like the Cubs will be interested in the offseason. More teams competing for a player means that said player can be worth even more.

"By that point, Crochet will be coming off a season of say, 140 to 150 innings. He already has thrown 111 1/3, more than double his career-high as a professional. His ability to remain a starter for the rest of this season is in question, so he would be a better match for an acquiring team in 2025 and ’26."

Another reason why the White Sox might hold off on a Crochet trade is that teams are leery of how many innings the oft-injured southpaw has left, considering he has already blown past his professional high. Will teams be willing to offer an absurd amount if Crochet only has a little bit left in the tank this season?

If Crochet stays healthy and reaches 140 or 150 innings as Rosenthal outlines, there won't be those concerns in the offseason. That could allow the White Sox to get more for Crochet as well.

By selling this season, the Cubs would, in theory, be adding even more pieces to an already strong farm system, giving them a prime opportunity to pull off a Crochet trade. Adding him to a future rotation already consisting of Imanaga and Justin Steele is extremely intriguing.

Would the White Sox be willing to send Crochet to their crosstown rivals? That's a different question, but the Cubs already have the pieces necessary to acquire him if they'd like, and should only get more ammo at the deadline by selling.