Woodruff is a bit of a risk after he pitched just 67 innings last season, so if the Red Sox do sign him, they wouldn’t count on him to be their ace. Nevertheless, he does have top-of-the-rotation upside after posting a sub-3.20 FIP every season from 2019 through 2022.
The 30-year-old even impressed in limited action last year, showcasing a 2.86 xFIP, 9.94 K/9, and 2.01 BB/9. One perk of signing Woodruff after he was non-tendered by Milwaukee is that Boston would have significant leverage. Not only could they sign him to a cheaper deal than the other players listed here, but they could also add option years to protect themselves if his injuries persist.
Cease is different than the rest of the names listed here because he is currently under contract with the White Sox. Therefore, in order to add him to their rotation, the Red Sox would have to trade for him. While parting with prospects is never ideal, doing so could allow Boston to land a top pitcher like Cease while simultaneously demonstrating the aggressiveness that Breslow promised when he was hired.
The 27-year-old put together a respectable 2023 campaign, amassing a 3.72 FIP, 10.88 K/9, and 4.02 BB/9. He has stayed healthy throughout his career, making at least 32 appearances over each of the last three seasons and averaging 5.1 innings per start during that span. There's a chance he could be acquired at a discount, too, given that Chicago appears sold on trading him this offseason.