#10 - Carlos Martinez: 5 years, $51 million, 2017
Carlos Martinez is one of those players that if you simulated his career 100 times, 90 of those results would have been better than what happened during his Cardinals tenure. Martinez showed so much talent and promise during his 9 years with St. Louis, but the end of his time still leaves a bad taste in the mouths of many.
At the time, his extension looked like a great value for St. Louis. He had been durable and on an upward trajectory each year, and was named to his second All-Star team in the first year of his extension. 2018 looked like an even better season for Martinez, posting a 3.11 ERA in 118.2 innings before suffering a season-ending injury.
Martinez was able to return as a closer the next season, and did so rather well, posting a 3.17 ERA with 24 saves. But the two seasons following, Martinez combined for just 102.1 innings with a 6.95 ERA. The Cardinals used his buyout following the 2021 season and he has not made it back to the big leagues since.