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5. Michael Wacha
Former thorn in the Cubs' side Michael Wacha is having a bit of a renaissance with the San Diego Padres with a 3.58 ERA in 50 innings with 45 strikeouts. At 31 years old, the Cubs could have definitely snagged Wacha at the unbelievably low price of 4 million the Padres are paying him in 2023. In truly one of the weirdest contracts I've ever set my eyes on, Wacha has a mutual option for 2024 worth $16 million, a club option for 2025 for $16, and a player option for 2026 valued at $6 million. This contract has Jed Hoyer written all over it and it would have been a great low-risk high reward deal with the same base salary as Michael Fulmer's deal.