You all know that I think the season is all but over, and yesterday’s blowout at the hands of Atlanta only served as yet another nail in the coffin. If the Dodgers wanted to see what they could get for guys like Ted Lilly, Hiroki Kuroda, Octavio Dotel, and the other veterans I’d be more than okay with that right now. That being the case, I’ve been thinking a lot about the future, and not only the overwhelmingly negative parts of it (like, how do you fill holes at catcher, second base, third base, left field, and 3/5 of the starting rotation with no money and few prospects?)

More specifically, I’m talking about the future of Clayton Kershaw, who at just 22 has lived up to the hype that accompanied his arrival. For the second year in a row, he’s in the top ten in the NL in most strikeouts per nine and fewest hits allowed per nine. He’s dramatically improved his control (walks/nine dropping from 4.8 to 3.8), he’s working deeper into games, and of his 24 starts this year, he’s allowed three earned runs or less in 20 of them. He’s awesome, he’s getting better, and he won’t even be 23 until spring training - a rare bright spot in what is quickly becoming a spiraling season.

I’m bringing this topic up now because the Blue Jays just signed their own young lefty, Ricky Romero, to a five-year deal, and it’s time to start thinking about doing the same for Kershaw. Romero and Kershaw are similar in many ways, each being lefty top-10 draft picks in their second full seasons, and MLBTR notes that Romero’s deal also bears similarities to deals that Jon Lester and Yovani Gallardo recently signed. At the time of the deals, all three had one more season left before arbitration, and at the end of the year, Kershaw will have 2 years and 105 days of MLB service, meaning he’ll probably fall just short of qualifying for “Super Two” status and arbitration eligibility.

All three signed deals for $30m over five years. Are those fair comparables for Kershaw? Let’s find out. Lester signed his before 2009, and Gallardo before 2010; I’ll use their stats at the time of the deal.

It’s not a perfect comparison, as Kershaw is younger than all three, yet will have far more starts under his belt by the end of the year than any had at the time of their deals. But the stats are similar, and nothing on that chart matters more than the nearly identical amount of service time, because that’s how these deals get made. The difference in value between a pre-arbitration year, the three arbitration years, and free agency years are astronomical, and when the time comes to make this deal happen, both sides will be looking at players in similar situations. The last remaining pre-arbitration year is really the big deal here; look at Zack Greinke and Josh Johnson, who each recently signed similar four-year deals, for $38m (Greinke) and $39m (Johnson). The average per-year salary on those two deals (north of $9m/year) were higher than any of our three comparables, but Greinke and Johnson each had more leverage because they had exhausted their pre-arbitration years and were poised to get huge raises in arbitration.

FanGraphs breaks down the difference between going yearly or signing long-term, and you can really replace Romero’s name with Kershaw in this quote, because the details are identical – even down to the 3.4 WAR produced in 2010.

Romero will finish his second year of service time in 2010 and would have been on a club-controlled contract for 2011. He would then be arbitration eligible for 2012, ’13 and ’14 and a free agent or 2015. Given the standard guide of 40%/60%/80% of market value expected for arbitration rulings, the five years of Romero’s contract add up to 2.8 seasons of free market worth plus one year at the league minimum. That is what Toronto and Romero are surrendering by not going year-to-year.

With a payment of $30.1 million guaranteed, that works out to the Jays paying Romero $10.75 million per market year. With current trends pegging the market dollars paid per win at around $4 million we have an estimation of about 2.75 to 3.0 wins per season for the contract’s middle point once we factor in the discount Romero should be offering for the security of a long-term deal.

Romero produced 2.7 WAR last season and is already at 3.4 this year so on the face of it, this looks like a possible win for the Blue Jays already.

They liked the Gallardo deal as well, noting that ”the new contract represents good value for the Brewers while providing ample personal security,” so unless you think Kershaw’s about to fall off a cliff, this is a sensible idea for the Dodgers, especially since he had the most WAR of the three in 2009 (4.2 to Gallardo’s 3.4 and Romero’s 2.7.)

So $30m over 5 years seems to be the going rate for this caliber of pitcher at this point in his career, and if you want to toss in a bit more because Kershaw is younger, that’d be fine by me too. If nothing is done, he’ll make less than a million dollars in 2011. That’s a steal. 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. So while I’m sure the responses here are going to be “sure, but the Dodgers are poor” (and it’s not that you’re wrong, it’s just that I’m trying to pretend we’re fans of a real baseball team for once), this is a deal that would save the Dodgers money in the long run.

Besides, if smaller teams like Toronto and Milwaukee can do it… there’s no reason the Dodgers shouldn’t be able to as well. This has the potential to be a painful offseason for a variety of reasons, and a commitment made to one of the game’s bright young stars would go a long way towards easing that.

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Don’t forget, tonight at 9pm PST is the deadline for the Dodgers to sign 1st-round pick Zach Lee. Unconfirmed reports are saying that they’ll offer him $3m to forget his LSU commitment and start his professional career. If that offer is accurate – and like you, I’ll believe it when I see it – whether or not he takes it is almost irrelevant, because that would be an offer higher than the Royals gave the #4 pick, Christian Colon. Should the offer be made and verified, then a lot of us may have a whole lot of crow to eat for our post-draft reactions.