Zack Greinke Aftermath: Will the Dodgers Waste Clayton Kershaw's Prime?

The staggering six-year, $206.5 million contract Zack Greinke received from the Arizona Diamondbacks on Friday night stunned the baseball world. Greinke is about to average $34.42 million annually, shattering the previous average annual value record of $31 million held by Miguel Cabrera and David Price, and yet the shocking part was that the big bad infinite payroll Dodgers were outbid by the small market Diamondbacks.

Greinke, 32, is coming off arguably the best year of his 12-year career. He had a major league best 1.66 ERA with a 19-3 record. For the past three seasons in which he compiled a 51-15 record with a 2.30 ERA, Greinke and co-ace Clayton Kershaw had formed the most formidable 1-2 punch in baseball. That's over now. After failing to re-sign Greinke, the Dodgers took the curious, and unusual step, of releasing a statement Friday night assuring fans that they had made the righty a strong offer and wished him and his family well.

Statement from Dodger president of baseball operations Andrew Friedman on Zack Greinke: — Los Angeles Dodgers (@Dodgers)December 5, 2015

In January 2013, the Dodgers announced a 25-year, $8.35 billion television rights deal with Time Warner. A year later, the deep-pocketed Dodgers turned around and gave Kershaw a seven-year, $215 million contract extension. At that time, it was the biggest contract given to a pitcher in baseball history. But the Dodgers could certainly afford it: they're pulling down an average of $334 million a year in TV revenue alone, even if the actual TV deal has turned out to be a nightmare.

It would be difficult to argue that Los Angeles should have trumped Arizona's Greinke offer just because they have this mammoth TV deal. In fact, the Diamondbacks were emboldened to sign Greinke because of their own new TV deal, a 20-year, $1.5 billion television pact signed earlier this season. Yet, the Dodgers media rights deal is worth five and a half times more.

But LA's refusal to outbid the Arizona is not why so many Dodger players were so frustrated on Friday night. Those close to Greinke said it was a fatal, and exasperating mistake, for the Dodgers not to engage Greinke in contract extension talks back in the spring and summer. According to sources close to Greinke, he was willing to talk. The club never made an offer.

By all accounts, Greinke and his family liked Los Angeles. Those close to Greinke said his wife, Emily, who gave birth to their first child this summer, wanted to stay. They had recently purchased a home in the valley not far from Dodger Stadium. But the Dodgers were said to be unwilling to extend their offer beyond five years. And ultimately Greinke followed the money. Sources close to him say he also likes the club's young players. Maybe he just didn't want to pitch to Paul Goldschmidt anymore.

The Dodgers have been in rebuilding mode ever since president of baseball operations Andrew Friedman took over the club's front office a year ago. He has spent much of his time trying to rid the major league roster of the previous regime's mistakes, and restocking a barren farm system. And while those are two noble pursuits, it doesn't change that in 2015 the Dodgers wasted one of the all-time great seasons from two starting pitchers. Greinke and Kershaw finished second and third in the National League Cy Young voting, a feat the Dodgers (or any other team) will be unlikely to replicate in the near future.

But Los Angeles was eliminated in the first round of the playoffs because the club failed to build around its two aces. Greinke was among the Dodger players who were particularly upset that the Dodgers' front office appeared to punt the trading deadline by picking up fringe players like Mat Latos and Alex Wood to replace the injured Hyun Jin Ryu and Brandon McCarthy, while other contenders added Johnny Cueto, David Price, Cole Hamels.

The Dodgers might not be in this situation had they traded for Hamels at the deadline last year. Hamels, a Southern California native, is owed $22.5 million per year through 2018, a relative bargain these days. The Dodgers also might have been able to reach the World Series—for the first time since 1988—last year with a rotation that included Kershaw, Greinke, and Hamels.

Kershaw has been the best pitcher in baseball for the past five seasons. And yet it's a lot to ask the soon-to-be 28 year old to continue pitching at this level when we know the horrible things throwing a baseball does to an arm. The Dodgers can't be certain Kershaw will remain healthy, which is why losing Greinke is as much about Kershaw as it is about Greinke. What will the Dodgers do now to build around this once-in-a- generation talent before his window of dominance closes?

Coincidentally, Greinke and Kershaw have the same agent. Not coincidentally, Kershaw insisted for an opt out clause after the fifth year in his seven-year contract extension in January 2014. He told me that wanted it after he seeing Greinke receive the same clause from the Dodgers in his six-year, $147 million free agent contract signed prior to the 2013 season. Barring catastrophic injury, Kershaw will almost certainly opt out of his contract with the Dodgers at the end of the 2018 season. And if the club fails to lock him up before that happens, the Dodgers and their fans will go through this all over again.

Now that Greinke is gone, the Dodgers currently have three healthy starting pitchers on their roster: Kershaw, Brett Anderson, and Wood. Losing Greinke would not be as devastating if the free agent market held viable alternatives. But with David Price, Jordan Zimmermann, and John Lackey all off the free agent market, the Dodgers will turn their focus to Johnny Cueto, who turned down a reported $120 million from the Diamondbacks earlier this week even though he is coming off an erratic season. The club could also pursue Mike Leake or Jeff Samardzija, or perhaps trade Yasiel Puig for another arm. They're going to have to get creative. This one is going to hurt.