Scott Erickson- 5 year/$32 million
Originally a fourth-round pick of the Minnesota Twins back in the 1989 draft, Scott Erickson quickly made a name for himself after leading the league with 20 wins and finishing second in Cy Young voting in just his second year in the majors (1991). Unfortunately, Erickson saw his numbers decline over the next three and a half seasons until he was traded to the Baltimore Orioles during the 1995 season.
The change of scenery worked well for Erickson, who finished the rest of the season with a 9-4 record with a 3.89 ERA and a 5.1 K/9 IP rate, one of the highest marks of his career.
He was rewarded with a five-year/$32 million extension during the 1998 season, this coming off a 16-7 and 3.89 ERA season the year before, his best season in the majors since that impressive ’91 campaign.
After signing his new, hefty contract, Erickson would make 78 more starts in an Orioles uniform, missing all of 2001 and 2003 with injuries. He went 15-12 with a 4.81 ERA in the first year of his deal, but managed a miserable 10-20 record and an ERA well north of 6.00 between 2000-2002. $32 million for 20 wins and 221 strikeouts.
He returned from injury in 2004, playing for four different teams over the next three seasons before calling it a career. He won just two games during that span.