From The Windup: Sorting Through the Latest Scott Boras Draft Power Play

From The Windup is FanHouse's daily, extended look at a particular portion of America's pastime.

There is one name that strikes fear into the heart of baseball fans and it's not Rodriguez or Santana or Sabathia or Ramirez. It's Boras. Signing or drafting a Scott Boras client means that your team is going to be put through every wringer possible as Boras tries to hustle, hassle, and finagle every last dollar out by exposing loopholes in agreements that no one ever even knew existed. At best, it's annoying for the fans to deal with. But a guy like Boras is exactly what baseball needs.

If you're unfamiliar with the most recent Boras saga, allow me to get you up to speed (for all of the details, read Dejan Kovacevic's excellent piece at the Pittsburgh Post-Gazette's PBC Blog). In June, the Pirates drafted Pedro Alvarez with the second overall pick. After little contact the day of the August 15th deadline, the sides worked out a $6 million signing bonus on the cusp of the midnight deadline. Things got suspicious from there when Alvarez never reported to Pittsburgh for his physical or to sign the contract in person.

After nearly two weeks, word broke last Wednesday that the Pirates had placed Alvarez on the restricted list for not signing his deal and that the player's union (the MLBPA) was filing a grievance alleging that the contract had been signed after the midnight deadline. From there, the finger-pointing started between Boras and Pirates' CEO Frank Coonelly (formerly the MLB General Counsel in charge of draft slotting) with the Royals' first round pick, Eric Hosmer (who signed after the deadline with an extension from the commissioner's office) dragged into the feud.

The entire process has cast some doubt on the character of Pedro Alvarez in the eyes of some Pirate fans. "Why does anyone ever hire Scott Boras? Why doesn't he just stick to his word?" Put yourself in Pedro Alvarez's shoes. Boras is a man that's constantly challenged the draft and won, reaping huge bonuses for his clients in the process. Who doesn't listen to that man? As someone that's only slightly older than the 21-year-old Alvarez, I can tell you that while this drama drives me crazy as a Pirate fan, I'd sign up with Boras and listen to what he told me in a heartbeat. Many people assume that Boras and Alvarez and wrong for doing this and therefore bad people. That makes the penny-pinching, monopoly-wielding MLB owners right and the good guys.

Beyond all of the moral implications of this saga, the real truth is that Boras is very, very good at his job, especially when it comes to the draft. A week ago, Kevin Goldstein at Baseball Prospectus put together a very informative primer on Boras's draft power plays over the last fifteen years. They are impressive. Everyone remembers J.D. Drew holding out for a year, but few people remember Boras exploiting a loophole to get Travis Lee, Bobby Seay, John Patterson, and Matt White declared free agents just week after the draft or how he snuck Landon Powell through the draft by getting him his GED a year early. Every time baseball closes a door, Boras finds five more. He's always a step ahead.

In life, everyone tries to find something that they love and then they try to find a way to get paid for it. Billy Beane turned down the Red Sox GM job because he loved the challenge of working with the small-market A's. It's what he was born to do. Scott Boras was born to exploit the collective bargaining agreement (CBA). Sure, the grievance is about money and sure, it's about beating his rival Coonelly, but it's also about Boras doing what he does. When it comes to finding loopholes in the CBA, Boras is the Rain Man.

That leads to the relevant issue at hand. Does Boras actually have a loophole here? He's playing an interesting angle this time. Instead of sticking it right to baseball, Boras apparently went to the Player's Association and alleged that the CBA was broken when MLB "unilaterally extended" the midnight signing deadline for Hosmer, Alvarez, and Aaron Crow (another of his clients that failed to come to an agreement with the Nationals). The grievance that's been filed isn't between Scott Boras or Pedro Alvarez and the Pirates; it's between the MLBPA and the Commissioner's Office, with the precedent set being applied to the Alvarez and Hosmer cases, as well as any other ones that are applicable. Involving the union is a stroke of genius here; it seems like they've won just about every relevant debate about the CBA since the days of Curt Flood. If Boras and the MLBPA are involved, you can be pretty sure they've got a leg to stand on.

It seems to me that if the Commissioner's Office gave extensions to the teams that asked for them and not to anyone else, both the teams and the players that negotiated past midnight had a clear advantage over everyone else and that has to be a violation of the terms of the CBA. That's not necessarily bad news for the Pirates and Royals, though. As the Goldstein article linked above points out, an arbitrator ruled in 1997 that MLB was wrong in changing eligibility rules after J.D. Drew went to play in an independent league, but the MLB executive council (the owners) were allowed to decide what to do with Drew and he was placed back in to the draft. It seems that a similar ruling might take place here.

How does it all play out? In the short term, it will likely seem like this is all for naught. The commissioner's office will get a slap on the wrist for breaking the CBA by offering the extensions. The Pirates and Royals seem almost certain to keep Alvarez and Hosmer for numbers close to their $6 million bonuses, no matter what the ruling on the deadline extensions is. The immediate net impact of this whole mess while likely be close to nothing.

The real reach goes beyond those two players, though. If the MLBPA loses the grievance and the arbitrator finds that the extension of the deadline is allowed, the deadline itself loses all of its meaning and Boras wins. If the MLBPA wins the grievance and the commissioner's office loses the ability to throw it's weight around at the signing deadline, Boras probably wins there, too. If the arbitrator allows a renegotiation after the deadline because the contracts were signed under false pretenses, Boras wins BIG time. The worst that happens for Boras is that the grievance is dismissed and two of his players have $6 million signing bonuses, which still feels kind of like a win. The pattern here is obvious. Young players hire Scott Boras for a reason.