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3. Kyle Hendricks
With each start that Kyle Hendricks has for the Chicago Cubs this season, it has been a question of if we will get "Good Kyle" or "Bad Kyle". For the most part, it has been "Bad Kyle" and when Hendricks has flashed his former "professor" persona, it's always been fools good.
In recent seasons, the Cubs have elected to skip Hendricks when he was scheduled to pitch against formidable lineups. With Hendricks set to become a free agent this winter, there is a better chance of him retiring than there is of him returning to the team for the 2025 season.
Even with the injuries that the Cubs have had this season, the Cubs' pitching staff should be in a good spot entering the 2025 season. Justin Steele and Shota Imanaga will sit at the top of the rotation with Jameson Taillon, Javier Assad, and Ben Brown falling in behind them. A return to health for top pitching prospect Cade Horton should also boost the staff in 2025.