Cubs' master trade deadline plan becomes all too clear after Ethan Conrad pick

The Chicago Cubs have developed a reputation in recent years for identifying and hitting on intriguing college position players in the MLB Draft, from Nico Hoerner to Matt Shaw to Cam Smith. Jed Hoyer and Co. were at it again on Sunday night, selecting Wake Forest outfielder Ethan Conrad with the No. 17 overall pick in this year's first round.

A well-rounded hitter who sprays line drives all over the field — he posted a 1.238 OPS with 15 extra-base hits in 21 games for the Demon Deacons in 2025 — and can play all three outfield positions in a pinch, Conrad figures to be a fast riser through Chicago's system. But scouting report aside, this pick is just as interesting for what it says about a couple of other Cubs outfield prospects, and what blockbuster plans the team might have in store at this year's trade deadline.

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Ethan Conrad pick could spell the end of Owen Caissie's time with Cubs

The Cubs enter the All-Star break on a high note, with consecutive wins over the New York Yankees in the Bronx that pushed the team's record to 57-39 and held its lead in the NL Central. With arguably the deepest and most dangerous lineup in baseball and Kyle Tucker set to hit free agency this winter, the time is now for Hoyer to go all-in and give his team the best possible chance to win a World Series.

Chicago's need at the deadline is clear: pitching, and preferably at least one frontline starter to replace the injured Justin Steele. To make that happen, the Cubs are going to have to dip into their well-regarded farm system, and that will likely mean saying goodbye to at least one of arguably their top two position prospects: outfielders Owen Caissie and Kevin Alcantara. Caissie, in particular, could be the centerpiece of a blockbuster package, as MLB Pipeline's No. 42 overall prospect is currently tearing the cover off the ball in Triple-A.

Of course, doing so isn't without risk. Not only could Caissie turn into a star in the Majors, but Chicago's outfield picture moving forward is less certain than it might appear: Pete Crow-Armstrong is locked into center field for the foreseeable future, but Tucker might bolt in a few months, and Ian Happ and Seiya Suzuki are both set to hit free agency after the 2026 season.

Moving Caissie, then, or even Alcantara (a top-100 prospect in his own right), threatens to turn a current strength into a potential weakness down the line. That is, unless Hoyer is thinking one step ahead: Conrad probably wasn't the highest-ranked player left on the board at the time, but drafting him feels like an admission that the Cubs know they'll need to replenish their organizational outfield depth sooner rather than later. And that should have fans primed for something big before July 31.

What could Owen Caissie fetch Chicago in a deadline trade?

This trade deadline figures to be relatively light on impact starters, and that means that the price for the ones who are available could skyrocket. If Chicago wants to nab someone like, say, Minnesota Twins ace Joe Ryan, or even a slightly lesser target like Merrill Kelly, Sandy Alcantara, Seth Lugo or Zac Gallen, they're going to have to win a bidding war to do so.

Their best chance will almost certainly include Caissie, a complete prospect who could help a rebuilding team as early as this season. He's almost a must if the Cubs want to fend off teams like the Los Angeles Dodgers, New York Mets and New York Yankees in trade talks, and it doesn't feel like a coincidence that Chicago is drafting with one eye the near future.