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3. Shane McClanahan
I know what you're thinking, the Rays would have to be out of their minds to trade Shane McClanahan, a guy who was in the conversation to win a Cy Young award a year ago. He also has not even reached arbitration yet and isn't set to be a free agent until 2028. So why would they move him, because it's the Rays that's why. Tampa Bay has an uncanny ability to bring in pitchers and turn them into aces. I'd be willing to give Tampa Bay a whole lot of pitching prospects to get this deal done. Call me crazy but hey this is hypothetical. A package consisting of Cade Horton (Cubs no. 4), Jordan Wicks (Cubs no. 5), Ben Brown (Cubs no. 7), and Caleb Kilian (Cubs no. 17) would be very enticing to the Rays and it would honestly be worth it from the Cubs standpoint. Put McClanahan in front of Marcus Stroman, Justin Steele, Jameson Taillon, and Hayden Wesneski and you have yourself a postseason rotation.