Trade the prospects? As Cubs eye deadline deals, Jed Hoyer looks to balance present and future

Typically, you can’t get a trade-deadline boost without parting with prospects.

But Jed Hoyer will have to walk a fine line as the Cubs try to improve ahead of a late-summer pennant race.

The Cubs’ president of baseball operations certainly has a wealth of young talent to deal from, with the team’s farm system boasting five of the top 100 prospects on MLB.com’s latest list. And those young players are extremely important to the Cubs’ fortunes past the 2025 season.

But opportunities to win the World Series don’t come around too often, hence the tough decisions Hoyer’s front office could face as it tries to win this year.

“That’s the balance, right?” Hoyer said Friday. “You want to focus on what’s happening right now but also realize we’re set up to have good teams next year and beyond. That’s the constant balance.

“We’re going to have really good teams after this year. I always keep that in mind. But this is what’s right in front of us, and this is really important.”

Outfielder Owen Caissie leads that group of highly ranked prospects, at No. 40. He’s on a hot streak at Triple-A Iowa, hitting .350 with a 1.480 OPS and eight homers in his last 10 games coming into Saturday.

The Cubs have been one of baseball’s best offensive teams all season long. And with Ian Happ, Pete Crow-Armstrong and Kyle Tucker soaking up playing time in the outfield – and designated hitter Seiya Suzuki able to slide into a corner spot when necessary – there’s no need for Caissie at the big league level.

“He’s been awesome, probably one of the best hitters in the minor leagues the last six weeks,” Hoyer said. “We haven’t had a need. We’re never going to bring him up to not play every day. That’s one of the things we’ve talked about a lot with our players in Triple-A. We have a lot of really good prospects there, and they need to develop. Bringing someone up to be in a bench role doesn’t make any sense.”

But Caissie doesn’t fit the bill of an expendable trade chip, either.

With Tucker set to hit free agency – and huge questions about whether the Cubs will be able to employ him past this season – Caissie seems like a pretty critical safety net should Tucker be playing elsewhere in 2026.

That’s got to make Caissie untouchable in trade talks, right?

“Like always, no one’s untouchable,” Hoyer said. “But at the same time, we have a lot of really good prospects, and you have to feel like you’re getting commensurate value. It really depends on what’s available”

Hoyer’s doing what any baseball-department leader does, keeping everything on the table as his phone starts buzzing leading up to the deadline.

The Cubs need starting pitching, their rotation and the depth beyond it thinned by injuries. They might also be in the market for a third baseman with rookie Matt Shaw struggling offensively.

Hoyer acknowledged it might require some creativity to cross those items off the Cub’s midsummer shopping list.

“This is a year where there might be some creativity because there’s not a ton of obvious sellers,” Hoyer said. “Some deadlines, it’s very obvious: ‘Here are the six to eight clear sellers, and they have a bunch of players that are available.’ This year, it feels like it may be a little bit of a different year.

“That’s one of the fun parts of this job, right? You kind of have to alter your playbook, you have to think about things differently.”

The Cubs have been down this road before.

In 2016, they prioritized winning in the present and won the World Series in part thanks to the contributions of trade-deadline addition Aroldis Chapman, the closer who cost them touted infield prospect Gleyber Torres, who started the All-Star Game last week.

A summer later, they did the same, dealing away highly rated youngsters Eloy Jimenez and Dylan Cease in exchange for Jose Quintana, the starting-pitching boost they needed in the moment.

But those trades are looked at quite differently in hindsight, mostly because of how the season played out: a ring in 2016, an NLCS exit in 2017.

Hoyer might have to consider a similar swap this summer as he tries to best position the Cubs to compete in October.

Unfortunately, only time will be the judge of any such move, making moving any prospect risky business.

Riskier still, however? Passing up a shot at a championship.