5. Darren Dreifort: Five Years, $55 Million, 2000
The gold standard for confounding pitching deals during the first free agency boom of the late '90s/early '00s, Darren Dreifort was everything Kevin Brown wasn't after the Dodgers panicked when he hit the market following the 2000 season. They could've simply let him walk. They chose ... unwisely.
Dreifort, a Dodgers bonus baby in the early '90s, missed the entire 1995 season and battled persistent arm issues during his career in LA, during which he posted a 39-45 record prior to reaching free agency. Scott Boras somehow played the Dodgers like a fiddle, assuring them that their fringe-average pitcher would be choosing the "rival" Colorado Rockies in the coming weeks. OK? You'll take that?
Somehow, that spooked the Dodgers, who paid Dreifort handsomely to post a 5.13 ERA in 16 starts in 2001 before missing the entire 2002 season to have elbow reconstruction surgery. According to doctors, he suffered from a degenerative tissue condition and a deformed femur, which threw off his mechanics and shattered his durability.
By 2004, those same doctors were warning he no longer had the capacity to be a starter. Dunno. Probably would've made a great Rockie.