A long-term Kershaw contract will assuredly be the largest ever given out to a pitcher, eclipsing the $180 million the Tigers gave to Justin Verlander. Kershaw could even approach the record $275 million given to Alex Rodriguez, though that high of a number now appears unlikely. The Dodgers and Kershaw reportedly briefly flirted with a $300 million "life-time" contract that would have seen him locked up for 12 years, but are closer to settling around $250 million.
Los Angeles wants a deal done by Friday's deadline to exchange arbitration numbers. Kershaw is entering his final year of arbitration eligibility and the difference in numbers between the two sides could be significant. This would be Kershaw's first time actually going through the arbitration process: He is coming off a two-year, $19 million deal that bought out his first two years of arbitration.
Kershaw and the Dodgers had been close to a $210 million deal over seven years in August, though the Dodgers hesitated and ultimately did not make the deal. That would have included an opt-out clause for Kershaw, allowing him to become a free agent after five years if he chose to exercise it. It's possible a deal made in the next few days could also include such a clause, which would allow him to become a free agent at the age of 30 and earn another huge contract.
Kershaw, 25, has been on an historic run. Over the past three years he has won two Cy Young awards and finished second once. He has led the league in WHIP and ERA each of the past three seasons and in strikeouts twice. Kershaw has not had an ERA over 2.91 since his rookie season in 2008, when he was 20 years old. In 2013, he had his best season yet with a 1.81 ERA, a 0.92 WHIP and 232 strikeouts. He has made at least 30 starts each of the past five years. Those numbers are even more incredible when one considers he has yet to reach his prime.
Even if the Dodgers are able to sign Kershaw, that may not be enough to remove them from contention for Masahiro Tanaka. Los Angeles' pockets run deep and when they are fixated on a player they seem willing to spend whatever it takes to land him. If the Dodgers do sign Tanaka and extend Kershaw, that would give the team three Casey Close clients signed long term in their rotation as those two would join Zack Greinke.