Cubs showing their trade deadline intentions with first, second-round draft picks

As soon as the Chicago Cubs' second-round pick was announced, MLB.com prospects expert Jim Callis commented on Jed Hoyer adding to the organization's position of strength. With the 56th overall pick, Chicago took speedy outfielder Kane Kepley out of the University of North Carolina, making it two straight outfielders to open up the 2025 MLB Draft.

Kepley isn't a head-turning guy. He's small, only 5'8" and 180 pounds, but the left-handed swinging speedster possesses elite bat-to-ball skills, leading the ACC this year in strikeout rate. His ability to create havoc on the bases reminds you of what we've come to love in Pete Crow-Armstrong. Kepley swiped 45 bags for the Tar Heels in 2025, which ranked second in the conference.

A quality defender, he joins first-round pick Ethan Conrad as Cubs' draft picks so far on Sunday night - but there's far less certainty in what Chicago is getting in Kepley, given his size and lack of pop.

Here's what MLB Pipeline has to say about him in their pre-draft scouting report:

Kepley is an on-base machine who executes quality swing decisions from the left side of the plate. He excels at putting the bat on the ball, especially within the strike zone, and rarely chases pitches. His lack of physicality and flat swing lead to worries about how much impact he'll make at the plate, though he does have some sneaky bat speed and strength that could give him some modest pull power.

Cubs loading up on outfield prospects in early on in the 2025 MLB Draft

Maybe it's simply taking the best player on the board, but given the trade rumblings that have been a constant in the background for weeks, it's hard not to read into this as a precursor to multiple trades involving outfield prospects.

Three of the Cubs' top five prospects (all of whom are top 100 talents, per Pipeline) are outfielders in Owen Caissie, Kevin Alcantara and James Triantos. If the Cubs are to check every box on their wish list over the next few weeks, which includes at least one starting pitcher, if not two, a late-inning arm and third base/bench depth, it's totally feasible we see more than one of these guys traded.

The simple truth is that's the strength of this system right now, and it looks like Hoyer and GM Carter Hawkins are pre-emptively backfilling the organizational outfield depth chart ahead of what's expected to be a very busy lead-up to the July 31 trade deadline.