Ever since Major League Baseball’s reserve clause was struck down in 1975 and pitcher Andy Messersmith signed a three-year, $1 million contract with the Atlanta Braves, free agency in baseball has thrived.
With the birth of free agency, however, also came a much greater responsibility for general managers and owners across MLB, who were forced to add the role of speculator to their resumes. It became their task to properly financially assess the value of each player relative to their skills and what they could potentially bring to their new team.
To say that some executives were better at that particular task than others would be a vast understatement. Throw into that the fact that smaller-market teams were forced to be much more budget-conscious, and the business of signing free agents literally became an exact science.
Signing free-agent pitchers has always been a bone of contention, starting with the very first one, Messersmith. After signing with the Braves, Messersmith was 16-15 with his new team in two years, the second year interrupted by injuries.
Messersmith was sold to the New York Yankees following the 1977 season, suffering through another injury-plagued season in the Bronx.
If that first contract was any indication, signing free-agent pitchers certainly has a risk/reward factor that is practically impossible to gauge properly. However, it hasn’t stopped MLB executives from taking the risk anyway.
The following is a list of the 30 most expensive pitching contracts in MLB history, with a somewhat educated opinion as to whether or not each pitcher lived up to that contract.