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Lucas Giolito
Lucas Giolito is in a very similar situation to Jack Flaherty: young pitchers with high talent who have shown signs of struggle throughout their careers. For his career, Giolito has a 4.22 ERA, 102 ERA+, 4.26 FIP, and 1.229 WHIP. He strikes out nearly ten batters per nine innings.
While these numbers aren't eye-popping, he has shown flashes of being an ace; he received Cy Young votes every year from 2019-2021. His age is also enticing to teams in search of starters. He will play most of the 2024 season as a 29-year-old. Whoever signs Giolito will be getting a strong starter with ace potential in the middle of his career.
This won't come cheap, however. It's tough to find comps for a pitcher of Giolito's talent and age. Most recently, we can find similarities in Marcus Stroman (3 years, $71 million in 2022 at age 30.6), Kevin Gausman (5 years, $110 million at age 30.8), Eduardo Rodriguez (5 years, $77 million at age 28.6), Trevor Bauer (3 years, $102 million at age 30), and Carlos Rodon (6 years, $162 million at age 30). Giolito's contract will most likely mirror that of Carlos Rodon's. Giolito is represented by CAA, a group that rivals Boras and Co. (Rodon's reps).
Prediction: 6 years, $150 million ($25 million AAV)