“You may have thought you heard me say I wanted a lot of money, but what I said was: Give me all the money you have.” (via)

As the Dodgers have gone on an unprecedented spending spree, there’s still the great white whale out there: the little matter of Clayton Kershaw, who will become a free agent following the 2014 season and certainly command a massive long-term deal. We know that Kershaw’s representatives and the team have had preliminary discussions about an extension, but so far nothing substantive has come out. (At least publicly.)

Over at FanGraphs this week, Dave Cameron notes that not only is Kershaw going to be a free agent in two more seasons, so are fellow aces Justin Verlander & Felix Hernandez. While that potentially sets up a phenomenal 2014-15 spending spree for teams looking to collect high-end pitching, I think we all know by now that players of that caliber almost never actually hit the open market. If even one of those three is a free agent that winter, I’ll be shocked.

Anyway, what’s going to happen in two years is a question for another time; for now, Cameron investigates what might happen if they were to sign extensions this winter, with two more years before free agency. Since Verlander & Hernandez had already signed contracts that bought out some of their free agent years, they’re making more than Kershaw is, and that might factor in:

Kershaw’s overall deal will probably reflect a slightly lower total, simply because he’s under contract for $11 million this year and is still bound by arbitration next year, and the Dodgers are under no compulsion to raise those salaries to something closer to the $20 million that Hernandez and Verlander are earning. So, even if he gets a higher AAV due to his youth and Dodgerness, we’re still probably looking at most a $25 million AAV for the years getting bought out, or $125 million from 2015 through 2019. If we assume his arbitration payout for 2014 would be in the $18 million range and the team just guarantees that as part of the deal, that would push his total value to $144 million over seven years.

I doubt that it’s a controversial statement to say that if the Dodgers were to sign Kershaw for 7/$144m, we’d all be dancing in the streets. But I’m also not sure it’s realistic.

Cameron is completely right when he takes into account that Kershaw isn’t yet a true free agent, so the Dodgers shouldn’t need to pay him for 2013 and 2014 like he is. While it’s popular to say that he’d be the first pitcher to break the $200m threshold, that’s only possible if he has two more excellent years and then hits the open market, free to negotiate with every team. That’s almost certainly not going to happen, so let’s keep those expectations in check.

Still, while Kershaw’s not going to get $200m, I’d be immensely surprised if he doesn’t at least surpass the 6/$147m that Zack Greinke just collected. After all, he’s younger, leftier, and simply better; it’s hard for me to see a scenario where he signs and isn’t the highest-paid pitcher on his own team, much less without potentially threatening records. Considering the influx of dollars into the sport over the last few years and the fact that he’d only be entering his age-27 season if he were to become a free agent, I think it’s not at all unfair to see Kershaw and his representatives look to challenge the 7/$161m that CC Sabathia inked with the Yankees prior to 2009.

Again, that deal was signed as a free agent, and Kershaw does not have the same bargaining power right now that Sabathia did on a completely open market, but you do have to wonder if four years of inflation plus the Dodgers becoming the financial behemoth that they are might make up the difference, or something close to it. Perhaps if you stick with the $11m that he’s getting this year, guarantee the $18m he’s likely to get in arbitration next year, and give him five years at $26m per season — allowing him to at least say he’s set a record for highest annual salary — you’d end up with 7/$159m, and that might sound about right.

Looking at it from another perspective, I actually think there’s a devil’s advocate argument to be made to not sign Kershaw this winter. Think about it this way – other than being a year closer to free agency, how much higher can his value really get? He’s coming off of two consecutive Cy Young-caliber seasons, and so there’s a limit to how much brighter his star can shine. But, don’t forget, he is coming off a hip injury that ruined his September and that – for a time – made us worry that ensuing surgery would keep him out well into 2013. While he did finish his year with an excellent string of starts and is reportedly feeling great heading into the spring, it’s hard to think that problem just cleared up and went away; I know I’d feel a lot more comfortable seeing him get a few months into the season without a recurrence before I bestow hundreds of millions of dollars upon him.

Talking about this kind of record-setting investment certainly makes the conversations we had two-and-a-half years ago about giving him 5/$30m seem quaint now, doesn’t it? From that piece, which makes me want to punch myself in the face right now: “But then he’ll be eligible for arbitration, and if he keeps on his current career path the yearly arbitration raises are going to get expensive and unpredictable. What if 2011 is his true breakout year, where he goes 21-6 with 212 K? We’ll be begging for the days when he might have been had for only $6m/year.” Lovely.

The funny thing is, I’m here throwing out numbers like “$159 million over seven years” without any thought about how the Dodgers might fit that into a budget, just because we don’t even know yet that they even have one. Again, I’m sure there’s a limit somewhere, but I really, really doubt that it’s going to be the young lefty ace on a Hall of Fame track that’s going to be where they draw the line; if it was, the Greinke money would likely have gone to Kershaw. Besides, people seem to forget that there really is a good amount of money coming off the books in the next few seasons; after 2013, you can say goodbye to $41.25m of Ted Lilly, Matt Guerrier, J.P. Howell, Skip Schumaker, Tony Gwynn, Mark Ellis, Juan Uribe, Jerry Hairston, & Nick Punto (assuming none are traded first). After 2014, nearly $32m of Hanley Ramirez & Josh Beckett goes away.

Either way, Kershaw is going to get paid, and soon. Seems the only questions are “when”, and “how much”; hopefully, we don’t have to worry about “by who?”