Derek Holland, now with 11 MLB seasons under his belt, has put himself in prime position to make the Pittsburgh Pirates 2020 roster. After spending eight seasons with the Texas Rangers, he signed with the Chicago White Sox in 2017 and posted some of the worst numbers of his career.
In 2018, he bounced back in a big way with the San Francisco Giants and was traded to the Cubs mid-way through the 2019 season, where he struggled again. There was no guarantee going into the 2020 season that he would land a job anywhere due to his age and declining effectivness in the league.