Some pluses and minuses of a Kershaw mega-deal

LOS ANGELES – On Wednesday afternoon, Clayton Kershaw will win his second Cy Young award in three years (presuming the baseball writers haven’t made an unlikely blunder), his reward for a season in which he led the major leagues in ERA for a third straight year. Four months after that, Kershaw will celebrate his 26th birthday.

One of those parties could go down in some style, though knowing what we know about Kershaw, probably nothing garish. He very well could be the richest baseball player of all time at one of those celebrations.

The only slightly puzzling part about the Dodgers’ attempt to lock up their young ace is why it hasn’t gotten done already. Kershaw has said he loves pitching for the Dodgers. The owners, most recently Magic Johnson, have said they consider him the best pitcher in baseball and plan on paying him accordingly. There is, of course, nothing urgent about the situation just yet. The Dodgers could just let Kershaw go through arbitration, pay him $19 million or so for next season, and take their chances next fall.

Nobody’s really talking about the details. Kershaw has insisted on a code of silence throughout the process, with only brief trickles of information emerging. The most interesting was a report by ESPN’s Buster Olney last month. Sources told Olney that Kershaw had been offered what amounted to a lifetime contract in the $300 million range, but walked away from it in the midst of the season.

Why? Because, “Kershaw was initially uncertain about committing to a deal so encompassing, and about having contract talks during the season,” Olney wrote.

OK, so the Dodgers haven’t played a game and Kershaw hasn’t thrown a pitch in nearly four weeks and still no deal. Unless it’s just taking a while for the sides to iron out the details -- quite plausible -- it might be that Kershaw is still feeling uncertain. Is he just embarrassed at the attention on his financial picture? Is he hesitant to forego free agency, the only time players truly find out what the rest of baseball thinks of them?

He’s not offering many clues. The Los Angeles Times caught up with Kershaw at a charity event not long ago and Kershaw gave mixed signals, saying he was “open-minded” to extending his deal with the Dodgers, but admitting he was “curious” about free agency.

If Kershaw is hesitant about committing the rest of his career to the Dodgers -- say, he wants to sign a six-year deal and enter free agency when he’s 32 and still has massive earning potential -- could he be doing the team a favor? The Dodgers, of course, are well aware that signing pitchers, the most fragile assets in baseball, to massive contracts is rarely a winning proposition. Kershaw worked nearly 259 innings last season and, given his age, his career workload is fairly staggering.

It wasn’t that long ago that general manager Ned Colletti committed $47 million to Jason Schmidt and watched Schmidt make 10 starts over three years due to a bad shoulder. Team president Stan Kasten was in Atlanta when two future Hall of Famers -- Tom Glavine and Greg Maddux -- walked, albeit at quite different stages of their careers than where Kershaw is.

And forget about injuries for a moment. As great as Kershaw is, is he worth two Zack Greinkes? Would you rather have the best pitcher in baseball pitching 20 percent of your games or a Top 10 pitcher working 40 percent of your games? The other contracts in the range of what Kershaw is rumored to be pondering, the Alex Rodriguez and Albert Pujols deals, aren’t exactly smelling like roses nowadays.

Those are the rational, baseball questions that make a Kershaw mega-deal a complicated proposition. But on the other side is this: Will these Dodgers owners, at a time their storied franchise is flush with cash, risk coming across as careless stewards? Can they gamble on letting the next Sandy Koufax walk out the door?