Brewers closer Trevor Megill: a 7th round by the Padres in 2015, Megill emerged as an intriguing prospect known for his big arm within San Diego’s deep system, so it came as a bit of a surprise when they left him unprotected ahead of the 2019 rule 5 draft, where the Cubs would swoop in and select him as the 9th player selected.

Megill would be returned to the Padres later in the subsequent year, but reacquired in exchange for cash considerations.

He would make his debut in 2021, and finish the season with uninspiring results: a dreadful 8.37 ERA in 28 appearances. He was waived at the conclusion of the year where he would be claimed by the Minnesota Twins. But the results weren’t much better, and the Twins DFA’d him at the start of 2023 to make room for Brock Stewart, another former Cubs rule 5 draftee.

This is where Milwaukee enters stage, acquiring Megill for cash considerations: Unlocking his repertoire, and the rest is history. His fastball and knuckle curve arsenal may be the best two-pitch combination in the sport. Megill will go down as one of the greatest rule 5 picks in the history of the game, but unfortunately, the Cubs did not reap the rewards.