Before 2010, Matt Kemp avoided arbitration by signing a two-year deal worth about $11 million. That deal expires at the end of this season, and Kemp will be arbitration-eligible for a final time in 2012 before reaching free agency at the end of next year. Kemp, of course, is putting up a season that looks more and more like it’ll be one of the best in Dodger history, as he’s on pace to hit 46 homers and steal 37 bases to go along with his .335/.420/.638 line. As the season goes on and the pennant race becomes a more and more distant dream, his contract situation is going to become a hot conversation piece. You can bet that he won’t be settling for two years and $11m again, but just how much money has he made himself with his performance this year?

Any conversation like this must immediately be prefaced with the usual disclaimer about deadbeat owner Frank McCourt and the uncertain financial situation in which the Dodgers find themselves. McCourt’s holding on to the ownership of this club on a bi-weekly basis as he scrambles to make each payroll, so it’s impossible to know what the situation will be when the season ends four months from now. Perhaps McCourt has managed to hang on until then. Maybe MLB will have taken over. It’s unlikely, but possible, that a sale could be in motion by then – or it could be some other scenario we can’t even dream about yet. None of that is going to change the fact that Matt Kemp is an extremely valuable asset who is going to get his money, so let’s pretend for the moment that we’re fans of a real team with responsible owners, and not the disaster we find ourselves in. (Additionally: minutes before I was to post this, I saw that Bill Shaikin is reporting that the McCourts have come to a settlement. We know none of the details yet, but Shaikin, Molly Knight, and Josh Fisher are usually nails on this story, so I won’t let the unknown there delay this post.)

Jon Heyman recently reported that Ned Colletti had initial conversations with Kemp’s agent, Dave Stewart, about a long-term deal, though clearly nothing has come of it yet. Despite Stewart’s well-publicized criticism of the Dodgers last season, that clearly seems to have blown over with the new on-field regime, and he and Colletti did just work together to sign Chad Billingsley to a deal earlier this year. I think every Dodger fan would like to see a long-term deal worked out, but let’s start small first.

What if Kemp goes to arbitration?

The record award for a position player in his third year of arbitration was the $15.5m that Prince Fielder got from the Brewers this past winter. Like Kemp, Fielder was coming off of a two-year deal and had not previously been to arbitration, though his deal had been for $18m, more than Kemp’s $11m. Arbitration panels are notorious for relying upon “old school” stats rather than more advanced methods, so we’ll stick with that here. In 2010, Fielder hit .261 with 32 homers and 83 RBI, scoring 94 runs. Kemp is on pace to top all of those marks this year. As if those numbers didn’t give him enough of an advantage over Fielder, he’s also on pace to steal the 37 bases, while playing a much more valuable defensive position. While Kemp is certainly going to be headed into the process with a better season in his pocket than Fielder, he’s also coming off a smaller contract and an uneven 2010. Those two factors mean that he may not break Fielder’s record, though it wouldn’t be surprising to see him come close. I could see Kemp getting anywhere from $13m-$15m in arbitration.

What if Kemp signs a long-term deal?

This assumes that Kemp wants to sign such a deal with the Dodgers. Outwardly he’s said all the right things, but we can’t really know for sure how frustrated he is with the current mess at the top and lack of talent around him, whether he’s enjoyed hitting on the road so much that he’d rather be away from Dodger Stadium more often, or whether he’d just prefer to be nearer to his Oklahoma roots. For the purposes of this exercise, we’ll figure he’ll want to stay. But at what cost? Let’s compare him to the two outfielders who signed $100m deals last winter, Jayson Werth and Carl Crawford. Like Kemp, each can kind-of sort-of play center field, but are much better situated in an outfield corner. (Age and stats for Werth and Crawford are through 2010, Kemp is to-date.)

Kemp compares favorably to both, and don’t forget that he still has the remainder of this season to complete; at his current pace he’ll overake Werth in WAR and lead all three in home runs. He’s the youngest of the three, and will likely be coming off the best season of any of them.  On the surface, your initial thought might be, “he’s going to get seven years and $130m”.

But while it’s fun to compare him to Werth and Crawford, it’s not entirely accurate. Each were free agents, able to play multiple teams off each other for the highest offer, and Kemp will not have that luxury until after 2012. His negotiating ability is somewhat limited by the fact that he’s still under Dodger control for another year and can’t go out to speak with other teams. So a more accurate comparison would be to players who have signed extensions with their teams that bought out a year or two of arbitration… and that’s where we run into problems.

After doing some research, I’ve found that it’s incredibly difficult to find a good comparison to Kemp. Players of his youth and talent rarely reach the open market, and often don’t even get as close to it as he will. (Crawford made it because everyone knew the cash-strapped Rays couldn’t afford the extension; the Phillies have so many other big-ticket deals that they couldn’t squeeze Werth in as well. Fielder and possibly Albert Pujols are likely to be good case studies this winter.) When I put the question to Twitter last night, looking for extensions that had been signed at a similar point in a player’s career, I got a lot of good suggestions, but none that were close enough. Evan Longoria signed his extension about a week into his MLB career. Hanley Ramirez, David Wright, Dustin Pedroia, Carlos Gonzalez and Justin Upton each signed after roughly two full seasons. Jay Bruce, Nick Markakis and Ryan Zimmerman signed before their first trips to arbitration. Ryan Braun signed an eight-year deal in his second season, then had a bizarre 5/$105m extension added which doesn’t even kick in until 2016. Kemp will have over five years of service time when this season ends – just one more of team control -  and that makes these calculations difficult.

The closest comparables I was able to find were Troy Tulowitzki and Ryan Howard, who each recently signed $100m+ deals to stay with their current clubs. Neither comp is perfect, for reasons I’ll state in a second, but for the moment let’s compare Kemp’s numbers to theirs. (Age and stats for Tulowitzki and Howard are through 2010, Kemp is to-date.)

Tulowitzki, like Kemp, made his debut in the summer of 2006. But he’s also a quality defensive shortstop, and hadn’t gone year-to-year like Kemp; after just over one full season, he signed a 6/$31m contract following 2007. When he signed his mammoth 10/$157.5m deal after 2010, it replaced the final three years of that deal. Howard’s situation is even more complicated (and controversial). He’s older than both and plays a less valuable position, and won a $10m contract in his first year of arbitration in 2008, then signed a 3/$54m deal to avoid going to arbitration a second time in 2009. That deal would have bought out his arbitration years and made him a free agent after this season… except that in April of 2010, the Phillies tacked on a ludicrous 5/$125m extension that doesn’t even kick in until 2012. If Kemp keeps up his current pace, he’ll top Tulo’s WAR and would come close to matching Howard’s.

All of which is a long way of saying, there hasn’t been a recent example like Kemp to point to. If he decides to play out his last year and hit the market, and has another good year in 2012, he’s likely looking at a massive $100m+ contract somewhere. If he signs a deal with the Dodgers, he’ll still get a hefty fee, but without the open market at play he’d probably have to leave some money on the table in exchange for avoiding the risk that would come with an injury or poor performance next season.

So let’s spitball this. It seems clear that if he finishes this season the way he started it, Kemp’s value on the open market could be between $15m-$20m a year. (I’m doing my best to avoid the fact that Howard got $25m a year well into his 30s, which is so insane I can’t even talk about it.) If he signed with the Dodgers (again, acting like we follow a real team) following 2011, he’d probably get on the lower end of that because he’s not a free agent and would pass up the 2012 risk. He’s also young enough that he might not want a 7-8 year deal like we’ve seen here, figuring that he could sign another big deal at around 31. So let’s start the bidding at… 5 years, $80m. Would you do that? Would he?