Boston Red Sox: 10 biggest first-round draft pick disasters

Red Sox 1995 Draft

No. 15 – Andrew Yount
No. 17 – Roy Halladay (Blue Jays)

Andy Yount had a promising debut in Rookie ball after the Red Sox selected him with the No. 15 overall pick in 1995 but his career quickly fizzled out after a miserable campaign the following year in Low-A Lowell. He latched on with the Detroit Tigers organization a few years later but converted to an outfielder after a pair of underwhelming seasons on the mound in A-ball. Yount couldn’t cut it with the bat either and his minor league career ended before he could advance beyond High-A.

If the Red Sox were intent on selecting a right-handed high school pitcher, they should have went with Roy Halladay. Instead, they left the future Hall of Fame pitcher for the division rival Toronto Blue Jays to take two picks later.

Halladay had some early career struggles, infamously being sent all the way back to Single-A to rebuild his delivery following a brutal 2000 season in the majors. By 2002, Halladay was one of the best pitchers in the game.

The eight-time All-Star won a pair of Cy Young awards in his 16-year career. He finished as the runner-up twice and had three others seasons where he finished in the top five.

Halladay spent 12 seasons with the organization that drafted him before the Blue Jays traded him to Philadelphia. He won his second Cy Young in his first season with the Phillies, highlighted by a perfect game in May of that season. Halladay helped the Phillies reach the NLCS that year by throwing a no-hitter in his first career postseason start.

The Red Sox were one of the rare teams that had some success against Halladay but they still would have been better off if he were pitching for them instead of against them.