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2010 (Pick 2) - Jameson Taillon, RHP, The Woodlands High School (TX)
Career Stats/Accolades: 859.1 IP, 4.03 ERA, 1.228 WHIP, 773 K, 54-41 W-L
The Pirates selected of the most highly touted pitching prospects of the last 20 years with the second overall pick in 2010. Jameson Taillon didn't make his MLB debut until 2016, six years after being drafted, due to injuries that caused him to be sidelined from baseball as a whole in 2014 and 2015. In 2017, he missed time with testicular cancer, and in 2018, he played his first full injury-free Major League season.
He played with the Pirates until 2019 when he injured his arm and missed the remainder of that season and the entire 2020 season. He was traded to the New York Yankees in 2021 for Maikol Escotto, Roansy Contreras, Canaan Smith-Njigba, and Miguel Yajure, and played in New York for 2 seasons before signing a four-year deal with the Chicago Cubs this past offseason.