No. 2 Jack Flaherty
Jack Flaherty was expected to be a massive 2023 trade deadline acquisition for the Baltimore Orioles, who have gone on to win their division and make the playoffs. But Flaherty has been one of the worst acquisitions at the deadline and barely is pitching now.
In previous years with the St. Louis Cardinals, Flaherty was showing he could be the next ace of the Cardinals, replacing Adam Wainwright, but that all failed after struggling in the 2022 season, which never stopped happening, including struggles in the 2023 season too.
After getting traded to the Orioles, Flaherty pitched in nine games, and he hasn't shown much, pitching to an ERA of 6.75 while costing them many games. His many struggles have been giving up hits because after his trade to the Orioles, he actually started to walk fewer people, but the hit rate skyrocketed to an unbearable rate.
Flaherty's two best MLB seasons were 2018 and 2019, the latter of which saw him finish fourth in Cy Young voting and even got some MVP votes. The Pirates are known to be able to revive the careers of former star pitchers, and that could be a huge possibility with Flaherty, who is still only 27 years old and could be a long-term solution for the Pirates' rotation.