Is Scott Boras still a good agent?

We all know the players, and the dollar values. Alex Rodriguez at $252 million. Barry Zito at $126 million. Johnny Damon at $52 million. Mark Teixeira at $180 million. These are some of Scott Boras’ greatest hits.

But, in the last few seasons his failures have been mounting as well. They don’t get as much attention as Boras’ victories. The super-agent has cemented his reputation as a money maker for his clients, but other than Mark Teixeira isn’t it beggining to seem like he’s failed more noticeably than succeeded of late?

Three major failures to read baseball’s free-agent market stand out: Alex Rodriguez, Manny Ramirez and now Johnny Damon. In each case Boras’ greed seems to have gotten the better of him, and his willingness to advise players to sabotage their teams to get to free agency makes it unlikely teams would want to work with him.

His handling of Alex Rodriguez’s opt-out still stands out in recent memory. At the end of A-Rod’s 2007 season, the third basemen’s best and one of the best season performances in Yankee history, Boras began leaking Rodriguez’s intention to terminate his contract before game 4 of the World Series. It remains unclear if Rodriguez himself even gave the go-ahead for this move.

In parallel, the money Boras wanted was almost an order of magnitude larger than what was available. Rumors circulated that he wanted as much as $320-$350 million for his contract. In the end, A-Rod nearly burnt his bridges with the Yankees before signing for $275 million. Much has been made about the bonuses he receives for his homers, but even with that extra-money Boras misread the market.

More recently, Boras has received blame for advising Manny Ramirez to sabotage his tenure in Boston to force a trade and get the team to bypass its options on 2009 and 2010. The existence of this rumor alone shows the low esteem the agent is held in. Once again completely failing to read the market makes the situation worse. Manny was holding out for a 4 year $100 million deal that never materialized. Instead, after initially rejecting the Dodgers 2 year $40 million offer he signed with Los Angeles for almost exactly that after spring training began.

Some may argue that Boras got it right with Mark Teixeira, but my mother could have negotiated Tex’s deal. Teixeira was entering his prime, had a history of high performance and good behavior, and came onto the market at a time when both the Yankees and Red Sox needed a first baseman. He was an easy sale and the measure of a salesman is his ability to make the tough deal.

Now, Johnny Damon is unemployed. After learning of the Javier Vazquez trade yesterday I was certain Damon would have signed for $20 million with the Yankees perhaps the same day. The team has traded its best left field option, bringing the team and the outfielder closer together. I now expect Damon to land with the Yankees more than ever.

But why did the team get to this point at all? Johnny wants to stay with the Yanks. The Yanks want him back. The problem, of course, is that player and agent are asking for way, way, way too much money. Damon has been reported as saying that won’t even consider talking to the Yanks for less than $13 million per season, before he came down a bit after the Nick Johnson deal. He’s also been said to want 3 or 4 years.

Damon just ins’t that good anymore, and its foolish for a team to offer so much money to an aging outfielder. Damon hasn’t signed anywhere else, so it seems as if, once again, Boras has misread the market.

Is Boras still a good agent? No one was better at getting teams to part with 8 and 9 figure contracts during the good times, but baseball seems to be moving away from albatross contracts. Boras, however, still demands them and his failures seem more abundant than his successes recently.

With teams losing money in the terrible economy and the list of bad contracts piling up, the blockbuster contract days may be behind baseball for a while. Boras’ principle job is to understand the market in general, and how it changes on a case by case basis for each of his clients. Of late, he’s had his finger on neither.

I’ll be paying close attention to how things play out for Damon and Matt Holiday. The deals those two sign will show if Boras really has lost his mojo.