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The following season, Taillon spent the entire season on the roster without being injured, pitching to a 3.20 ERA in 32 starts. He was 14-10 in 191 innings. In 2019, Taillon's season was cut short due to a forearm injury, he was shut down for the remainder of the season on August 2, 2019 as he would undergo surgery. He was 2–3 with a 4.10 ERA in 7 starts. On August 14, he underwent surgery to repair a flexor tendon as well as UCL revision, a condition that could make him miss all of 2020 as well.

2017 was Taillon's first season in the starting rotation. He was placed on the disabled list in May as he underwent surgery for testicular cancer. He was activated in June. In 25 starts, he pitched to an 8–7 record and 4.44 ERA.

Taillon underwent surgery for testicular cancer on May 8, 2017 and made his first rehab start three weeks later, giving up one run in three innings.

Taillon returned in 2016 with the Indians, where he made 10 starts before earning his first major league call-up. Taillon went 4–2 with a 2.04 ERA, striking out 61 in 61.2 innings and walking only 6. On June 8, Taillon was recalled to make a spot start with the Pirates, who decided to push back Francisco Liriano's start one day after they played a doubleheader the day before. Facing off against fellow 2010 first rounder Noah Syndergaard in his debut, Taillon threw 6 innings, giving up 3 runs on 6 hits, 2 walks, and 3 strikeouts, not receiving a decision in the eventual 6–5 loss. After the game, Taillon was optioned back to Triple-A, but not without receiving compliments from his manager Clint Hurdle on his effort, saying "This kid's poured into everything he's done. It's been a great fight back." However, his stay in Indianapolis was very brief, as an injury to Gerrit Cole necessitated a move to bring Taillon back into the rotation. On June 14, Taillon made his second start, also against the Mets, throwing 8 scoreless innings, carrying a no-hitter into the seventh before it was broken up by Curtis Granderson, and recording his first win in the 4–0 victory. He spent the remainder of 2016 with Pittsburgh. In 18 starts he compiled a 5–4 record and 3.38 ERA.

Taillon underwent Tommy John surgery in April 2014 to repair damage to the ulnar collateral ligament of the elbow in his throwing arm, costing him the 2014 season, while a sports hernia caused him to miss the 2015 season.

Prior to the 2013 season, Taillon was ranked as the 15th best prospect in baseball by MLB.com. Taillon participated in the 2013 World Baseball Classic for Team Canada, being the youngest member of the team at age 21. He began the season with Altoona and was promoted to the Indianapolis Indians in August. In 26 games (25 starts) between both clubs, Taillon compiled a 5–10 record and 3.73 ERA.

Taillon describes his pitch repertoire as being a four-seamer at 94–98 mph, a two-seam fastball at 93–96, a "power" curveball with diagonal break, and a circle changeup. He says of his pitch selection, "I feel pretty confident right now that I can throw pretty much any pitch in any count."

Taillon was named to appear in the 2012 All-Star Futures Game. He began the season with the Bradenton Marauders and he was promoted to the Altoona Curve in August 2012. In his first week with the Curve, August 20–26, 2012, Taillon was named the Eastern League pitcher of the week. In 26 starts between the two teams, he was 9–8 with a 3.55 ERA.

Taillon made his professional debut with the West Virginia Power against the Hagerstown Suns on April 27, 2011. He joined the team on April 24 after staying in Florida for an extended spring training assignment. He spent the whole season with the Power, going 2–3 with a 3.98 ERA in 23 starts.

Taillon was drafted by the Pittsburgh Pirates in the first round of the 2010 MLB draft. He had signed a National Letter of Intent with Rice University in November 2009 posing a challenge to the Pirates in their effort to sign him. However, hours before the signing deadline, the Pittsburgh Post-Gazette reported that Taillon had indeed signed with the Pirates. Baseball America's Jim Callis reported that Taillon's deal included a $6.5 million signing bonus, the second-highest in draft history.

Jameson Lee Taillon (born November 18, 1991) is a Canadian-American professional baseball pitcher for the Pittsburgh Pirates of Major League Baseball (MLB). Taillon was drafted by the Pirates as the second overall pick in the 2010 Major League Baseball draft.

Jameson Taillon was born in Lakeland, Florida to Christie and Michael Taillon on November 18, 1991. As he was born in Florida and his parents were born in Canada, Taillon is a dual citizen of the United States and Canada. Taillon attended The Woodlands High School in Texas. He caught the attention of Pirates scouts with a 22–6 high school career record. He was 8–1 his senior year and threw a 19-strikeout no-hitter against rival Conroe High School on March 23, 2010.