Halladay spent 16 seasons in the majors with the Toronto Blue Jays and Philadelphia Phillies. A promising prospect with a decent rookie season, he was so bad in his second major league season with the Blue Jays that he was sent back to the minors. But he reinvented himself and eventually became a six-time All-Star in Toronto, winning the AL Cy Young in 2003.

A trade sent him to Philadelphia before the 2010 season, where Halladay had the finest season of his career: He won the NL Cy Young with a 2.44 ERA over a league-leading 250 2/3 innings. His season included a perfect game in May and a no-hitter in his postseason debut in October. He’d have one more All-Star season in Philadelphia before his career began to come to an end. He ended his career with a 203-105 record and a 3.38 ERA.

Since retirement, Halladay has been a pitching coach for his sons’ teams and a volunteer instructor with the Phillies. If his tweets are any indication, he’s spent a lot of time flying and fishing over the past few years.

Halladay’s plane, the ICON A5, was first released in 2008. The lead aeronautical engineer on the A5, Jon Karkow, was killed in a crash in May along with a passenger, Cagri Sever. An NTSB report said pilot error was to blame.