Colorado Rockies first baseman/outfielder Ian Desmond: 5 years, $70 million (in theory)
The Colorado Rockies signed shortstop/outfielder Ian Desmond before the 2017 season to a five-year deal for $70 million … to play first base.
The problems with that were that a) Desmond had never played first base and b) was not a great offensive player before the Rockies signed him. He had an OPS+ of 93 in the two seasons prior to signing with the Rockies.
So with the Rockies, he was awful at first base so they moved him back to the outfield and he didn’t hit. From 2017 through 2019, he had an OPS+ of 82 and an rWAR of -2.6.
He opted out of the 2020 and 2021 seasons and he forfeited his salary for the two years, making it a three-year deal for $45 million.
Colorado Rockies starter Darryl Kile: 3 years, $24 million
It may not sound like much but in December 1997, a $24 million dollar deal was a big deal. That’s what the Colorado Rockies gave to Darryl Kile to become their ace. At the time, the most lucrative deal in MLB history was signed the previous offseason by Albert Belle when the White Sox gave him five years and $55 million.
Kile was 5th in the NL Cy Young voting with Houston in 1997 and he was an All-Star too.
Compared to the era in 1998, Kile actually wasn’t terrible (100 ERA+ and a 2.2 rWAR) but his ERA was 5.20 and he led the NL in losses (17), which were two key stats of the time. He was even worse in 1999 as he had a 6.61 ERA in 32 starts.
The Rockies traded him to St. Louis (sound familiar?) where he regained his former form until he passed away in June 2002 in Chicago while with the Cardinals at the team hotel due to a heart attack.