Now, the 25-year-old left-hander is about to become the highest-paid pitcher in baseball history.
Kershaw and the Dodgers have agreed to a seven-year, $215-million contract, according to people familiar with the situation who spoke under the condition of anonymity because the deal isn't expected to be announced until Friday.
At $30.7 million per season, the average annual value of the contract is the highest ever for a player at any position.
Although Alex Rodriguez's 10-year, $275-million contract with the New York Yankees remains the highest in total value, Kershaw's deal ranks first among pitchers. The previous record contract for a pitcher was the seven-year, $180-million contract Justin Verlander signed with the Detroit Tigers last winter.
Kershaw will have a chance to enter the free-agent market at 30, as his contract includes a provision that allows him to void the remainder of the deal after five seasons.
For the Dodgers, the agreement allayed their fears that Kershaw could become a free agent at the end of the upcoming season.
Kershaw, who earned $11 million last season, was eligible for salary arbitration for the final time this year. The Dodgers made it a point to reach a deal by Friday, the deadline for teams to exchange salary figures with their arbitration-eligible players.
Kershaw and the Dodgers started talking about extending his contract last spring. Kershaw wanted the negotiations to remain private and was noticeably irritated when details of the discussions were leaked to the media in June.
A couple of weeks after the Dodgers' season ended, Kershaw acknowledged he was "curious" about free agency.
The Dodgers didn't want Kershaw to test the market.
"It's our desire to sign him here for a very long time," General Manager Ned Colletti said last week.
Under the ownership of Guggenheim Baseball, the Dodgers had the wherewithal to persuade him to bypass free agency.
The Dodgers have taken on close to $1 billion in salary commitments since the team was purchased from cash-strapped Frank McCourt and emerged from bankruptcy almost two years ago. Including Kershaw, the team has five players under contracts with average annual values of more than $20 million. Six players are signed through the 2017 season.
The team's opening-day payroll figures to be about $250 million this year, which would establish a club record.
And the Dodgers might not be finished. Team President Stan Kasten said Wednesday that a deal with Kershaw wouldn't affect the Dodgers' other plans. In other words, the team could still sign Japanese right-hander Masahiro Tanaka, who is expected to land a contract worth more than $100 million.
Tanaka, 25, is represented by Casey Close, who is also the agent for Kershaw and Zack Greinke. Greinke signed a six-year, $147-million deal with the Dodgers last winter.
A Texas native, Kershaw came to the Dodgers at 18, when he was selected with the seventh overall pick of the 2006 draft. Kershaw made his major league debut less than two years later and drew immediate comparisons to Dodgers Hall of Fame pitcher Sandy Koufax.
Kershaw won his first Cy Young Award in 2011, when he led the NL in wins (21), ERA (2.28) and strikeouts (248). He won the award again last season, when he posted a career-best ERA of 1.83. He has started 31 or more games in each of the last five seasons, including 33 in each of the last three.
Kershaw's career ERA of 2.60 is the lowest among starters who have pitched 1,000 or more innings since 1901. His record is 77-46.
Kershaw has also made his mark off the field, building an orphanage in Africa and raising money for various charities.