Dec. 10, 2024: Guardians acquire RHP Luis Ortiz, LHP Josh Hartle and LHP Michael Kennedy from Pirates in exchange for 1B Spencer Horwitz

A couple hours after acquiring Horwitz, the Guardians promptly flipped the middle infielder to the Pirates in exchange for Ortiz and some prospects. It’s been a runaway win for Cleveland.
Although the trade was considered a bit risky at the time, Ortiz has been a good fit for a Guardians’ starting rotation that struggled with injuries this year. While Ortiz is still a work in progress (4.64 ERA in 75 1/3 innings), he’s shown that he has the makeup and arsenal that the Guardians covet in their starting pitchers.
On the other side, Horwitz has hit .228 in 28 games this year with the Pirates, and would have been an awkward fit on a Guardians roster that already has too many first baseman.
Dec. 21, 2024: Guardians acquire RHP Slade Cecconi and Competitive Balance Draft Pick (Round B) from Diamondbacks in exchange for 1B Josh Naylor

A year after Naylor earned his first career All-Star nod, the Guardians sent him to the desert ahead of his impending free agency after this season, and, as of now, it’s a trade that hasn’t aged very well for the Guardians.
Naylor entered play on Wednesday hitting .302 with nine home runs and 49 RBI for the Diamondbacks, and could be in line for being an All-Star for the second straight year.
But the story of this trade hasn’t been written just yet. The Diamondbacks are currently sitting at .500 in the suddenly-loaded American League West, which has led to Naylor’s name being floated on the rumor mill.
JOSH NAYLOR #WALKOFF GRAND SLAM! pic.twitter.com/AmjDiTVAI2
— MLB (@MLB) June 10, 2025
While the Guardians saved about $10 million by trading Naylor, that ended up being a moot point after they signed Carlos Santana to a one-year, $12 million deal on the same day they traded Naylor.
Santana’s putting together a vintage season for the Guardians (albeit at the expense of the Guardians’ youth movement), while Cecconi is beginning to round into form after missing the start of the season with an injury.
The Diamondbacks are the winners of this trade as of now, but there's still a good bit of this story that needs to be written.