#15 Francisco Liriano, 3-year $39 million
Francisco Liriano was a pitcher who played for the Pittsburgh Pirates from 2013 to 2016. Liriano was acquired by the Pirates in a mid-season trade with the Minnesota Twins in 2012 and quickly became one of the team's most reliable starting pitchers. His initial contract with the Pittsburgh Pirates worked out, it was a 2-year deal. In 2013 he owned a 3.02 ERA while in 2014 he earned a 3.38 ERA.
After two strong years and two playoff appearances, the Bucs decided to bring Liriano back during the 2014-2015 offseason. The Bucs handed him out one of their biggest free agents contracts ever by giving the lefty a 3 year $39 million deal. In 2015 he would go on to once again own an impressive ERA at 3.38. However, that would be it.
The year that this free-agent contract became bad was in 2016. Liriano owned one of the worse ERAs in all of Baseball in 2016, 5.46 in just over 100 innings pitched. This is why this contract ended up being one of the worst in Franchise History.
At the trade deadline, the Pittsburgh Pirates offloaded Liriano to the Toronto Blue Jays. This trade was not well received by any means. First and foremost the Bucs only received one player back in the deal, in Drew Hutchinson. At this point, Hutchinson was considered a bust and there were really no expectations for him upon joining the Organization. Going the other way with Liriano were former first-round pick Reese McGuire and one of the team's top 20 prospects in outfielder Harold Ramirez.
Both McGuire and Ramirez have carved out Big League careers in their own right. Hutchinson never panned out with the Pittsburgh Pirates, being released by the Organization in 2017. Meanwhile, the Bucs gave up two solid prospects and paid bascially half of the extension Liriano was given. Not a good deal, but they did receive a successful 2015 from him, making it somewhat more favorable than the others.