14) Carlos Lee-6 years, $100 million
The first two entries on the list also happen to be the two best players to appear on the list. El Caballo was great during his stint in Houston and earned the money they gave him. That he appears on this list is no fault of his own.
During his time in Houston, Lee hit .286 with an .817 OPS. He appeared in all 162 game the first year of his contract and drove in 533 runs in the 815 games he appeared in. So how does Lee make this list?
The six years, $100 million Houston gave him in 2007 is the type of money the Astros balk at fifteen years later under a more aggressive owner. It backfired immensely on the Astros, as they were able to surround the slugger with virtually no help, missing the playoffs all six seasons. Lee's deal is similar to the deal the Rockies gave Kris Bryant while simultaneously not even attempting to be competitive.
One man can't make a team win in the MLB. Just ask Mike Trout. Jeff Luhnow went on to trade Lee in the final year of the deal, jump starting the Astros' rebuild that led to the golden era of today.