Clayton Kershaw, Adam Wainwright, & Big-Money Starting Pitcher Contracts

When I saw the news that the Los Angeles Dodgers had inked ace southpaw Clayton Kershaw to a seven-year deal worth $215 million, I did what I suspect many St. Louis Cardinals fans did. I giggled because LA had just guaranteed Kershaw a seven-year deal that was worth over twice as much money as the extension the Cardinals and Adam Wainwright agreed to before the 2013 season began. But, having dug deeper into the various starting pitcher contracts over the last couple years, I'm not so sure I should've giggled with quite so much glee.

I took a step back and looked at the deals that were signed close in time to Waino and the Cardinals' extension, as well as Kershaw's. There is no real apple-to-apple comparison. While they're all pitchers, their respective contracts were inked at different points in their respective career arcs.

The following chart looks at these deals. All the dollar values are in the millions, of course. The light gray cells indicate years before the pitchers' extensions kicked in. The light green cells are those covered by the extensions. The dark green panels are years for which an option exists under the contract. All contract information is from Cot's Baseball Contracts.

*The Giants have a $21MM club option for Cain in 2018 with a $7.5MM buyout.

*The Phillies have a $20MM club option for Hamels in 2019 with a $6MM buyout.

*The Mariners have a conditional $1MM option on Hernandez in 2019 if he spends more than 130 days on the DL due to a right elbow injury.

*Verlander has a vesting option for 2020 that is based on finishing in the top 5 of the 2019 Cy Young vote.

*Kershaw has the option of opting out of years six and seven of his contract with the Dodgers after his age 30 season.

Kershaw is a rare bird. The lefty has won two NL Cy Young awards. And he's just now entering his age 26 season. When Waino was entering his age 26 season, he had just completed his first in the big-league rotation, with a 3.70 ERA and 3.90 FIP. Wainwright would not even receive a Cy Young vote until 2009, his age 27 season.

After Wainwright's age 28 season, his ulnar collateral ligament (UCL) tore. It required Tommy John surgery, a procedure that has become something of a rite of passage for many big-leaguer hurlers. Kershaw is not one year removed from missing a season for Tommy John surgery and rehabilitation like Wainwright was when the Cardinals signed him to an extension.

Putting together this chart made me somewhat worried about the Cardinals-Wainwright extension. Of those pitchers shown on the chart, Wainwright is the oldest pitcher entering his deal, which means he faces the greatest likelihood of an age-related decline during his contract (although that Verlander contract sure looks like a fledgling albatross). Add to that Wainwright's injury history and the Cardinals' extension of the wagonmaker might very well be the worst deal on the chart. And that was before Wainwright threw 276 2/3 innings during the 2013 regular season and playoffs.

There is an injury risk for any pitcher, which makes all pitcher contracts gambles to an extent. After all, throwing a baseball about 100 times every fifth day is a taxing activity. In a vacuum, I'd rather guarantee a pitcher six years, as the Cards did with Waino, than seven, as the Dodgers did with Kershaw. But I think I'd rather have a two-time Cy Young winner entering his age 26 season under contract for a guaranteed seven years and $216MM than a pitcher under contract for six years at a total cost of $109.5MM who has never won a Cy Young, but has undergone Tommy John surgery and is entering his age 31 season. Especially if I had money to burn like the Dodgers and I thought he might opt out after the fifth year.

What do you think?