Originally posted on Race Review Online  |  Last updated 1/12/12

What we are witnessing this offseason is the baseball equivalent of Haley’s Comet. For the first time in a long while, we are seeing something very, very unusual—failure by Scott Boris. As of today, we have one finalized failure (Ryan Madson’s one year, $8.5 million deal to be a closer-in-waiting for the Reds) and one impending failure (the fact that Prince Fielder is still on the dried-up market). Ah, what a sight to behold! 

Don’t get me wrong, I am a huge fan of Madson. As a Phillies fan, I loved seeing him in the bullpen. His devastating fastball/changeup combo was perfect as a setup man (and no time more than the magical 2008 season), and this past year he proved he had the chops to close too. Heck, I would have preferred the Phillies pay him 44 million over 4 years over Jonathan Papelbon 50 million over the same time frame.

Also, as a baseball fan, I love watching Prince Fielder mash. The dude has super-human strength. He is literally must watch television. If I know he is coming up to bat in the next half-inning, I am staying in front of the TV for the extra 10 minutes, punctuality be damned. I’d even go so far as to say that the Angels will regret handing Pujols a massive contract instead of Prince (but that is a whole other can of worms).

All that to say, I love those two guys and want to see them make as much money as they can. BUT...

Despite loving the players, I despise their agent and not just because he’s screwed my Phillies over. Sure, there may be lingering bitterness over refusing to let JD Drew sign with us after we drafted him second overall, but there is more too it than that; It is the whole way he operates. Sure he doesn’t call hookers like Dan Lozano (allegedly), but Boras just has an unlikable air about him. He is ruthless and out to squeeze as much money out of teams (even small market franchises) as possible. What makes him so good is what makes him so dislikeable. Like Herman Cain I don’t have the facts to back this up, but Boras has probably gotten every team in the league to sign a “what-the-heck-where-they-thinking?!?” contract at least twice.

But although Scott Boras has been proficient and ruthless at securing top-notch contracts for his clients in the past, why has he struggled so much this winter? I would venture to say (and because I am the writer, I will say) that the answer is a combination of two things. First, Boras has finally over played his hand, and second, that he has built up enough ill-will around the league and it’s finally catching up to him.

Now confession, the first reason isn’t really all that original to me; people were saying the same thing even before anyone was signed this offseason. The big question of the Winter Meetings (at least in terms of free agents) was how were both Fielder and Pujols going to get the massive contracts they wanted when none of the traditional big market teams seemed to need (Phillies, Red Sox, Yankees, White Sox even the Angels who had a good season from rookie Mark Trumbo) or be able to pay (Mets and Dodgers). That left the Cubs as the only traditional big market team that needs and can most likely afford a big name first baseman. Sure, there is the nuevo riche of teams like the Rangers, Marlins, and Nationals, but the Rangers and Nationals didn’t really need to spend out the wazzu for a star first baseman, and the Marlins have spent their money elsewhere. Now, when so few teams seem to be interested in even one legitimate superstar, how is an agent supposed to drive up the price for a second star? Clearly, the market conditions were working against Boras and Fielder.

The closer market though differed from the first base market. There was a fair bit of shuffling around in the closer market this year, and let’s be honest, what team wouldn’t like to upgrade their closer role, even if they already had a closer on the team already? And yet, Madson stayed on the market. Even after guys like Papelbon, Heath Bell, Andrew Bailey, Houston Street, Sergio Santos, even Joe Nathan were signed or traded for, Madson remained a proven closer, a fantastic setup man, and a free agent. In the end, Madson had to accept a one year deal to replace Francisco Cordero and hope that the closer market next year would be more accommodating to him.

But unlike Fielder (to this point), Madson had a chance at signing a long term deal to be the closer for a contender. Rumors had the Phillies offering Madson a 4 year, $44 million deal to stay on as their closer. What happened next is hard to explain (mostly because we’ve never really gotten clear explanations from either camp), but the end result was the Phillies kicking Madson to the curb and signing an even more expensive closer—Papelbon. Since the Phillies signed a more expensive option to close, we can assume that lack of money wasn’t the nail in the coffin. Do the Phillies really think Madson is that much worse than Papelbon? After the past few years, I’m not so sure that there is a big difference talent-wise between the two. And it seems that Madson was willing to take the $44 million. Boras himself said that he had advised the Phillies that Madson would accept a 4 year, $44 million deal, though Phillies GM Ruben Amaro Jr. denied that there was ever a deal in place. Days later the Phillies had Papelbon signed for $50 million.

So what actually happened in the short time frame between rumors of a Phillies/Madson deal and the Phillies signing Papelbon? Without actually listening in on those negotiations one can only speculate as to the particulars of the breakup, but the obvious elephant in the room is ego. Guys like Scott Boras and Ruben Amaro Jr. (GM for the Phillies) have a ton of it; the moxy and self-confidence that it takes to reach their respective positions is a fertile breeding ground for ego. It may not have been the main factor in his decision, but don’t try and tell me that Ruben Amaro Jr. didn’t get some pleasure out of screwing over Scott Boras.

At the end of last season, it seemed like a certainty that Madson was leaving town, and even when negotiations between the him and the Phillies started, they always seemed contentious. No one can say for sure that Boras had finally rubbed raw one too many egos, but eventually what goes around comes around—even Haley’s Comet.

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