4. Mo Vaughn: Six Years, $80 million, 1999
Mo Vaughn was a star with the Boston Red Sox. He was a three-time all-star and an MVP winner. He was coming off of a season which saw him slash .337/.402/.501 with 40 home runs and 115 RBI for the Sox. He finished fourth in the MVP balloting.
The Angels signed Vaughn to that six year deal after his outstanding season and made him the highest paid player in baseball history. It's safe to say they'll want that one back.
Vaughn's first two seasons went pretty well as an Angel. He slashed .276/.362/.503 with 69 home runs and 225 RBI in 1999 and 2000. He averaged 34 home runs and 112 RBI in those seasons which the Angels would definitely take.
The problem is what happened after the 2000 season. Vaughn missed the entire 2001 season due to injury and then issues with his weight caused his body to break down a bit early. He was traded to the Mets before the 2002 season and finished his career just two seasons later.
Vaughn played well when he was on the field, but physical issues limited him to just two seasons with the club. The Angels wasted most of the money on this deal, which at the time, was the largest in history.