Todd Helton

A Colorado legend, Helton was one of the best pure hitters of his generation. He consistently hit above .300 while still hitting for power year after year. The Rockie-for-life was rewarded a mega contract for his efforts midway through his career.

As Helton aged, the Rockies decided to rework the last two years of his contract, giving him $9.9 million for two seasons, while he deferred $13.1 million over 10 years. He hasn’t played since 2013, yet is getting $1.31 million per year until 2023, plus 3% annual interest.