Originally posted on Fangraphs  |  Last updated 8/20/12

Two months ago, Dale Sveum said this about shortstop Starlin Castro, who forgot how many outs there were on a potential double play ball:

“It’s something that’s obviously unacceptable at any time,” Sveum said Monday.

“Whether we could have turned the double play or not is irrelevant to not knowing how many outs there are in the most important part of the game. These things have got to stop happening or he’s going to stop playing.

“These kind of things are things that my son does in high school, maybe.”

Well, I’m pretty sure Castro won’t be getting benched any time soon, as the Cubs have reportedly agreed to sign him to a seven year, $60 million contract extension that should be finalized in the next week or two. The deal contains a team option that gives the Cubs control over Castro through the 2020 season, buying out up to four free agent seasons in the process.

So, yeah, Castro’s job security isn’t really a question anymore. The question now is whether this was the right bet for the Cubs to make.

On the one hand, Castro can be a frustrating player. He’s been prone to mental lapses like the one cited above, he’s been chided for a lack of hustle at times, and his approach at the plate seems to be getting worse, not better. On the other hand, Castro is just five months older than Deven Marrero, the Red Sox first round selection in the most recent June draft, and Marrero is currently playing in the short-season New York-Penn League. That Castro is in his third year in the Majors and holding his own at this point in his career is a sign of his legitimate talent.

The list of shortstops who have posted better offensive numbers than Castro in 1,000+ plate appearances through age 22 is very, very short. In the last 60 years, in fact, the list is only four players long – Alex Rodriguez, Cal Ripken, Jim Fregosi, and Wil Cordero. Shortstops who got to the Majors early and hit worse than Castro has to date? Gary Sheffield, Alan Trammell, Robin Yount, and Jose Reyes all fall in that category. These are the kinds of history lessons that make you want to lock up Castro now, before he takes a big step forward offensively and starts seeing free agency looming in the near future.

However, those kinds of facts ignore the fact that Castro hasn’t really improved much since getting to the big leagues in 2010. He’s posting career worst marks in walk rate strikeout rate, and BABIP, all of which is leading to a 91 wRC+, worse than he posted in either of the last two years. His defense has improved, and there are fewer questions now about whether he can remain at shortstop, but his offense hasn’t progressed as quickly as the Cubs would have hoped. Of course, he’s still an above average shortstop even at this level, but usually, large contracts like this are given to players who begin to establish new levels of excellence. Castro’s contract bets on that leap coming before it has actually materialized.

History suggests that the leap probably is coming. Most guys who are above average players from 20-22 become excellent players in their mid-20s, and Castro certainly has the physical tools to become an excellent player. If Castro follows a normal development curve, he could easily be a +4 or +5 win player by the time he would have reached free agency, and a contract to keep him in Chicago then would have been two or three times the size of this one. So, if this is the cost of keeping Castro in Chicago through his twenties, then it’s probably better than not signing the deal and going year-to-year, as that would bring legitimate risk of a breakout season pushing his costs up very quickly.

However, given the contracts that have been handed out to other players at similar spots of their career, the Cubs didn’t really get much of a bargain here. Thanks to MLBTradeRumors extremely useful Extension Tracker, we can identify five other players with similar levels of service time who were also going to qualify as Super-Twos, meaning that they got an early bite at the arbitration apple and were due for larger raises earlier in their career. Going back to 2008, here are the players who signed multi-year deals as Super-Twos with between 2-3 years of service time:

Player Age Avg WAR Years Dollars Team Options Robinson Cano 25 2.8 4 30 2 Cole Hamels 25 3.6 3 20 Tim Lincecum 26 5.6 2 23 Jay Bruce 24 3.0 6 51 1 Gio Gonzalez 26 2.5 5 42 2 Starlin Castro 23 2.7 7 60 1

Age represents their first season covered by the extension, while average WAR is their career total prorated to either 600 PA or 180 IP, depending on whether they are a hitter or a pitcher. Hamels and Lincecum decided to take shorter deals that would not delay their free agency, and their 2012 performances show the relative benefits and costs of betting on their own future performance. Hamels came out far ahead of where he would have otherwise, while Lincecum might regret not taking a long term deal when he had the chance.

Among those who did sign away free agent years, though, it is interesting that there’s a nearly perfect linear increase in terms of years and dollars with each each extension. Cano got 4/30, Gonzalez got 5/40, Bruce got 6/50, and Castro has got 7/60 – in each case, the guaranteed dollar amount went up by $10 million for each additional year added on. And, note the relationship between length of deal and age – including the team options, the contracts for Bruce, Cano, and Castro all end after their age 30 season despite the fact that they signed them at different ages. Bruce and Cano were coming off better seasons than what Castro has posted this year, but he had youth on his side, which is why (along with inflation, anyway) he got more guaranteed money than either one.

The other notable takeaway from these contracts? You probably don’t want your best young players qualifying for Super-Two status. For comparison, both Justin Upton and Andrew McCutchen also signed long term extension for $51 million over six guaranteed years with a little over two years of service time under their belts when they signed the deal, and both were coming off substantially better seasons than what Castro has put up this year. Castro got more guaranteed money than either one despite being an inferior player because of that extra year of arbitration eligibility.

Had Castro been called up a couple of months later in 2010, he would have been looking at another year of near-minimum salary, and would have been negotiating from a significantly reduced amount of leverage. If you look at the deals signed by the like of Alexei Ramirez and Dustin Pedroia, you’ll notice that Castro’s Super-Two status probably got him an extra $10 to $20 million over the life of the deal.

The Cubs can’t undo the service time clock, so they were faced with a decision to do this now or wait until he has a breakout season and then try to lock him up at a higher price. History says that breakout is probably coming, so as long as Castro didn’t need that future paycheck to serve as a motivational tool, they were probably wise to get this deal done now. The combination of Super-Two status and his exceptionally young age just didn’t do them many favors when negotiating, however, and Castro ended up pretty well compensated relative to other players in a similar situation. Now the Cubs just have to hope that the expected breakout comes sooner rather than later.

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