Tim Anderson did what he could with contract extension

It’s been a couple years since we’ve seen the front side of an early extension, and it seems even longer than that. In the two years since Adam Eaton signed his five-year deal with two club options, the White Sox have traded him and another one of their best business decisions (Chris Sale) while dangling the other (Jose Quintana) for months.

While the Sox struggled in vain to escape the crushing disappointment, fans and media often sought to project a residual dissatisfaction onto those players. It’s not without logic — they had signed away years of the years of their prime for well below the market rate, and the White Sox could only surround them with more expensive players who performed far worse.

If one of expressed a morsel of regret during the death throes of the team’s hopes, it’d be understandable. Yet neither Sale nor Eaton took the bait, and Quintana hasn’t, either. Even Sal Perez, the most underpaid of them all, never openly complained about the five-year, $7(!!!) million extension while he was en route to becoming the team’s leader and World Series MVP. (His new agents did that for him, and the Royals reworked the pay structure with a new extension afterward.)

Seeing Anderson’s excitement after signing a six-year, $25 million extension (with two club options worth $26.5 million) makes it easier to understand why they don’t kick themselves, at least hard enough for us to see.

Scott Merkin said Anderson reminded him of the others, and considering all of them have young families, it’s easy to see the incentive of securing eight figures early, even if they miss out on the opportunity to earn an additional eight figures over the same period by going year to year. Until the pay structure changes at the minor-league and pre-arb levels, the gamble between taking early money and maximizing earning potential will always be pronounced. There’s a lot of bus rides and mattresses on floors in between the signing bonus and the MLB debut.

Moreover, Anderson didn’t sell himself for cheap considering the circumstances.

The deal is the most lucrative contract given to a position player with less than one year’s service in baseball history. The previous record deal given to a position player that wasn’t eligible for arbitration before his third full season was Tampa Bay Rays third baseman Evan Longoria’s $17.5 million deal, signed just weeks after his major league debut in 2008.

This contract can easily become another super-bargain even though it broke new ground, but it seems like Anderson’s side did what it could at this point in time. When Sale and Quintana signed their deals, they fit comfortably within a bunch of other extensions, most of which were no-brainers for the team at the time, and everybody inside and outside the organization reacted accordingly. Pitchers can get really expensive through arbitration, and John Danks vs. Gavin Floyd/Sale/Quintana is a good example of the kind of money the Sox saved with extensions for their arms.

Here, thanks to Anderson’s severe walk-to-strikeout disparity, the White Sox are courting a little bit more uncertainty than usual. It’s probably closest to Eaton, whose contract extension had the least immediate surplus value due to his sketchy health record and skills that weren’t rewarded handsomely through arbitration. Despite their numerous differences, they’re players who have multiple useful skills, but won’t dominate the categories that arbitrators recognize.

Knowing what we know about Anderson’s game, it’d take an optimistic trajectory to get Anderson to even $20 million over those first six years. The White Sox signed him for $25 million over the same period. That extra $5 million or so was the fee the White Sox paid to hold club options on his first two years of free agency at potentially below-market prices ($26.5 million total). It also keeps insures the Sox against Anderson becoming a multiple-time All-Star, and any ugly arbitration-year battles that might result from differing perceptions of worth.

It’s a bet worth taking, because as Eaton shows, all it takes is one good year to justify the whole expenditure. It’s also nice to see a player earn more than a team is obligated to pay him during his physical prime, since pre-arb players are already tremendously undercompensated. Anderson could be as big a bargain as the others who signed early extensions if he makes even one more step in his game, but the blame will lie with baseball’s pay structure rather than his agents. If the past is any indication, Anderson still probably won’t regret it.