After signing his new seven-year, $215 million extension, Clayton Kershaw is officially the highest paid player in baseball. He'll become the first player in the sport's history to crack an average annual salary of more than $30 million. And, because he also got the right to opt-out of the contract after the fifth year, there is a pretty good chance that this won't even be the largest contract of Kershaw's career. With a few more dominant seasons and relatively few health problems, Kershaw could hit free agency again at age 30 and command another monster contract. By the time he retires, Kershaw may very well have earned more than $400 million in salary.
For contrast, let's take a look at Chris Sale. While Sale doesn't have Kershaw's reputation, he's actually No. 2 in baseball (behind only Kershaw) in ERA -- since he debuted in 2010, and it's not as though he's outperformed his peripherals in a significant way; he's No. 6 in FIP- and No. 3 in xFIP -- over the same time period, so no matter how you prefer to analyze a pitcher's performance, Sale rates as one of the game's best starting pitchers.
However, Sale chose to cash in early in his career and signed a long-term extension with the White Sox last spring. The deal guaranteed him $32.5 million over five seasons, and then gave the White Sox a pair of team options. If both are exercised, the total deal will pay Sale approximately $58 million over seven years, with the potential for a little more than $60 million if he finishes highly in the Cy Young voting during any season during the contract. Like Kershaw, Sale is in line to hit free agency after his age 30 season, and like Kershaw, he simply needs to stay healthy and keep pitching well for the next few years in order to set himself up for a monstrous paycheck that will carry him through his 30s.