Scott Boras and Arbitration Clients - I

Serpentine Smile Dept.Not that Edwin Jackson is the #1 target of the offseason ... but it is an interesting question whether the Bora$ factor rules Jackson out as a Mariners option.

As Sir Anthony would say, this is Mission Impossible.  Difficult should be a walk in the park.  ::winning smile::  ... is a Jackson contract extension (and therefore Tigers-Mariners deal) "difficult" or is it "impossible"?

Cool Papa with pointed commentary that deserves its own thread, especially because I'd like to see somebody chime in with data:

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CPB:  There is absolutely no way that Boras will even consider a contract extension. Boras' number one rule, the Prime Directive that any player must agree to if they are going to hire him, is to go free agency as soon possible. That is where he can work his magic and secure a monster deal.

:raises eyebrow:

I took a little tubular around the internet, looking for Boras clients who were:

1. Arb-eligible pitchers
2. Talented enough to potentially score real big $$ in their 7th years
3. Willing to sign an extension selling their clubs a free-agent year or two

A first turn around the 'net didn't turn up any particular examples.   The first half-a-dozen Boras clients we found, all waited for their contracts to expire before signing their next one.

Does anybody know of any cases in which an arb-eligible Boras client did not go into the free agent market at the first opportunity?

Here's an Oct. 2008 (or later) list of his clients, via MLBtraderumors.com:

Tony Abreu Garret Anderson Rick Ankiel Jeff Baker Josh Barfield Carlos Beltran Adrian Beltre Hank Blalock Chris Bootcheck Julio Borbon Willie Bloomquist Chris Coghlan Alex Cora Joe Crede Johnny Damon Chris Davis J.D. Drew Stephen Drew Jacoby Ellsbury Prince Fielder Eric Gagne Carlos Gomez Carlos Gonzalez Mike Gonzalez Craig Hansen Luke Hochevar Matt Holliday Edwin Jackson Andruw Jones Jair Jurrjens Ian Kennedy Byung-Hyun Kim Gerald Laird Matt LaPorta Jeff Larish Kyle Lohse Felipe Lopez Rodrigo Lopez Derek Lowe Ryan Madson Daisuke Matsuzaka Kevin Millwood Zach Miner Xavier Nady David Newhan Magglio Ordonez Micah Owings Mike Pelfrey Carlos Pena Oliver Perez Guillermo Quiroz Manny Ramirez Anthony Reyes Alex Rodriguez Ivan Rodriguez Max Scherzer Scott Schoeneweis Bobby Seay Ryan Spilborghs Julian Tavarez Taylor Teagarden Mark Teixeira Jason Varitek Ron Villone Jarrod Washburn Jeff Weaver Jered Weaver Matt Wieters Barry Zito

Boras has demonstrated his own financial acumen a dozen times over at this point.  It's tough to believe that he would never pencil out the math and arrive at the conclusion that a young pitcher should avoid the risk and lock in his first $30-40m of wealth.

A lot can happen to Edwin Jackson in two years -- especially injury.  But also including a downturn in his career.  What if he takes an Erik Hanson career path from here?  Bill James called Hanson the #3 pitcher in the AL after his 1990 season.  Hanson simply threw his arm out and lost his stuff.

.............

The first $30-40m changes Jackson's life, security, and peace of mind, more than the next $3 billion would. 

Of course, you could argue that Jackson's already going to pass the $10m mark in earnings with this arbitration award, and has hit this "permanent security" point already.  

But I would question that.  After taxes, lifestyle, and all the rest of it, I wonder whether Jackson would have more than $2-3m in his financial portfolio at the end of next season.   Probably many athletes like him have less.  It's nothing unusual for athletes who have made a boatload of money to be broke a few years after retirement.   I'm skeptical that a first major arb award has that kind of effect.

I would think that it would be a guaranteed $7 + $10 + $12 + $12m deal -- $40m -- that would assure Jackson of being a rich man for life.

................

The question is whether Boras sometimes does wrong to his arb clients, by passing up contract extensions so that he can go to war with the owners.

I'd like to know the answer to that.

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Part II