1. Cleveland Guardians
The team that makes the most sense to strike a deal with is the Cleveland Guardians. One of the best teams in all of baseball currently has a starting rotation that sits just 12th best overall in the American League and 24th overall in MLB. The Guardians currently have a five-game lead in the AL Central, where they will surely be looking to strengthen for a postseason push.
Cleveland does have several prospects in the top 100; however, they are mostly at lower levels, which won't help the Cubs soon enough, or they are guys like Kyle Manzardo, a lefty first baseman that the team needs no longer has a strong need for unless they decide to push Michael Busch back to third base. Cleveland does, however, have an interesting arm in Daniel Espino that would intrigue the Cubs.
Espino is a roll of the dice due to recent injury history that has spanned the better part of the past two seasons, but there's no doubt the upside is there. He's been listed as high as the #14 prospect in baseball, according to MLB Pipeline two years ago. Currently, he is the #5 prospect in the Guardians' organization, and it will be interesting to see if they're willing to move him at the deadline. He currently owns a 2.45 ERA in four starts in double-A, striking out an absurd 35 batters in 18.1 IP.
At just 23 years old, he's the type of target the Cubs should be eyeing if they believe the injuries are behind him. A decent prospect from the Cubs may be needed as a sweetener, but we've seen the Cubs acquire great prospects in the past for mere rentals. Now, willingness to move on from starting pitching with multiple years left of control may make these two teams a match made in heaven at the trade deadline.