This Chicago Cubs Prospect Most Likely to be Traded at Deadline: MLB Insider

The Chicago Cubs are one of the few teams that look to be sure-fire buyers ahead of the MLB trade deadline.

With a 51-35 record, they are three games ahead of the Milwaukee Brewers in the National League Central. If they want to remain in that spot and continue keeping pace with other contenders, they need to be aggressive in upgrading their roster.

Right now, starting pitching is likely their No. 1 need.

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The improvement of the bullpen has helped compensate for the starting pitching, with Daniel Palencia, Chris Flexen, Drew Pomeranz and Brad Keller all performing exceptionally well.

But the Cubs need depth behind Shota Imanaga with Justin Steele sidelined for the year. 

Matthew Boyd has been excellent, but the team has struggled to get consistent production from Jameson Taillon, Ben Brown, Colin Rea and Cade Horton.

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Chicago is in a position to make a splash, should the opportunity present itself, given how deep their farm system is.

The Cubs have several Top 100 prospects currently in the organization who could be used as the center piece of a trade package to bring back the kind of starting pitching the team needs to truly contend for a World Series.

Who is the most popular youngster of the bunch?

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As shared by Jim Bowden of The Athletic (subscription required), more than 40 executives around the league were polled, including mostly presidents of baseball operations and general managers, the name that came up the most was Owen Caissie.

“Caissie was the prospect mentioned the most by execs — and it wasn’t even close…Five years ago, the Cubs acquired Caissie as one of the prospect headliners in the Yu Darvish trade with the Padres. Now, in all likelihood, they will trade him for pitching at the deadline,” Bowden wrote.

Outfield is the one position Chicago currently doesn’t need any help, blocking Caissie’s way to the Major Leagues.

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However, there could be some hesitancy from the Cubs part to move on from him becuase he is the perfect Kyle Tucker insurance.

Set to hit free agency after the season, if the star slugger departs, Caissie could find his way into the Opening Day lineup in 2026.

He certainly looks ready for the opportunity with a slash line of .271/.373/.480 in 193 games at Triple-A Iowa and 836 plate appearances.

Caissie has hit 31 home runs, 47 doubles and five triples, stealing 14 bases and knocking in 108 runs.

For more Cubs news, head over to Cubs On SI.