Colorado Rockies left-handed starter Denny Neagle: 5 years, $51 million
The Colorado Rockies signed Denny Neagle to a five-year, $51 million deal in the same offseason that they signed the aforementioned Mike Hampton. In fact, Neagle was signed just eight days prior to Hampton.
In 1997, Neagle came in 3rd in NL Cy Young voting and was an All-Star. He wasn’t that caliber when the Rockies signed him but he was still a decent pitcher.
However, Neagle only played in three of the five years of the contract with Colorado and he pitched to a 5.57 ERA (91 ERA+). He missed all of the 2004 season due to elbow surgery and in late 2004, he was arrested in Colorado. Therefore, the Rockies were able to cancel the last year of his contract due to a morals clause. He never pitched in the majors again.
Colorado Rockies infielder José Reyes: 6 years, $106 million
In all fairness, the Colorado Rockies did not sign this awful deal but they did agree to acquire it. The Miami Marlins signed this deal in the 2011-2012 offseason and, later, they traded it to the Blue Jays. The Blue Jays eventually passed it on to the Rockies in the Troy Tulowitzki deal in July 2015.
Reyes was awful with the Rockies in 47 games (-0.2 rWAR) but he was going to be their shortstop in 2016. However, he was suspended by MLB for choking his wife and shoving her into a door while on vacation in Hawaii. The police were called and he was arrested. Charges were later dropped since his wife refused to comply with authorities but he still was suspended for 51 games.
The Rockies sent him to the minors on a rehab assignment but before he was called back up, they designated him for assignment, partially because a rookie shortstop by the name of Trevor Story proved that he was much better than Reyes.
For all of those issues and the awful production, the Rockies had to pay Reyes $29.46 million. Not a great trade for the Rockies and it wasn’t a good trade for Toronto either.