No. 2 Mike Leake:
After being outbid in the last hour by the Red Sox for David Price and losing both John Lackey and Jason Heyward to the Chicago Cubs, the Cardinals made a classic panic signing by signing Mike Leake to a five-year, $80 million deal.
During his short time in St. Louis, Leake pitched 330.2 innings with an ERA of 4.46 and WAR of 1.5. Part of Leake’s downfall was his groundball pitching style on a ball club that ranked 28th in team defense in 2016, per Fangraphs, but did rise to a respectable level in 2017. Regardless, his career ERA before joining the Cardinals was 4.15 and his contract was a headscratcher.
While arguments have been made that the value that Leake provided was not actually all that bad, $16 million a year for a guy whose ERA with the team was 4.46 is nothing to celebrate and forced the Cardinals to hand him to Seattle just a year and a half into his deal and pay a large chunk of his contract for practically nothing in return.