No. 2: Marcus Semien, Chris Bassitt, Rangel Ravelo and Josh Phegley to the Oakland Athletics for Jeff Samardzija and Michael Ynoa - December 2014
Samardzija, a longtime member of the Chicago Cubs, had only just wrapped up his only season with the A's when he was flipped to the White Sox in exchange for this monster return.
He made a full season of 32 starts in 2015 but had a 4.96 ERA and 79 ERA+ along the way. He led the American League in hits allowed, earned runs and home runs surrendered.
Ynoa stuck around for a bit longer, functioning as an oft-used middle relief option for the Sox in 2016 and 2017. In 45 games and 59 innings, he posted a 4.42 ERA and 95 ERA+ with 53 strikeouts and 39 walks.
Ravelo never amounted to anything for Oakland and is currently a member of the San Diego Padres organization on a minor-league contract.
Phegley spent parts of five years with the A's, primarily functioning as the team's backup catcher. He never had much of a bat but was known as a strong defender for the club.
Bassitt and Semien represent the two biggest losses here for the White Sox. The 2021 All-Star made 100 appearances with Oakland over six years, posting a 3.44 ERA and 121 ERA+ across 526 innings. He spent last season with the Mets and continued to improve across the board.
Now, he is expected to shore up the middle of the Toronto Blue Jays rotation in the next few seasons after signing a three-year deal north of the border.
Then there's Semien, who made himself into one of the best power-hitting second basemen in baseball history. He also made the All-Star Game in 2021 and hit 45 home runs that year, the single-season record amongst second basemen.
Since he left Chicago, he has hit 178 home runs and driven in 530 with a 110 OPS+. He would be a much better option at the position than Leury García, Josh Harrison or Elvis Andrus have been over the years.