Scott Boras may be the best-known - and most feared - agent in baseball, but he hasn’t exactly had a free agent season for the ages this year.  Instead of masterminding a series of record-setting deals tied to his name this winter, Boras has had to endure a a series of offseason embarrassments.

First up, Johnny Damon, the best free agent still on the market. Four years ago, Boras was able to parlay Damon’s strong regular season numbers - and postseason stardom - into a four-year, $52 million contract from the New York Yankees. This year, the outfielder is still among the ranks of baseball’s unemployed, despite his great 2009 season and his daring two-steal dash to help the Yankees win the World Series.

So what happened? It looks like Boras went way too high for way too long with the Yankees. It took him forever to budge from his initial two-year, $26 million contract extension demand, which was an unreasonable one for a 36-year-old in this market, even given the stellar season Damon had. Brian Cashman and the Yanks eventually countered with a two-year, $14 million offer, but the two parties were unable to come to an agreement, despite Damon repeatedly saying that he wanted to remain a Yankee. Instead, the Yankees moved on to sign Nick Johnson and Randy Winn.

Granted, Cashman eventually made an insulting $2 million offer to Damon, claiming that was all he had left in his budget (ha!), but it should have never gotten to that point.

Then there’s free agent second baseman Felipe Lopez, another Boras client still on the unemployment line.  Make that an ex-Boras client - Lopez fired Boras last week. According to ESPN.com’s Jayson Stark, Lopez “was reportedly disgruntled over still finding himself without a team” despite a 2009 season in which he “batted .310, with a .383 on-base percentage.” Stark noted that “the only other free agent on the market this winter who matched or beat him in both of those categories was Matt Holliday.”

Holliday, another Boras client, was the agent’s main success stories this winter, with his seven-year, $120 million deal from the St. Louis Cardinals. However, that deal still pales beside what Boras originally claimed Holliday’s value was - the agent was suggesting earlier this winter that the outfielder was was worthy of a contract similar to the eight-year, $180 million contract Boras got for Mark Teixeira the season before.

Boras had similar tough talk this winter about how much Adrian Beltre was worth. He reportedly wanted a four-year, $40 million deal for his client, and compared Beltre to fellow free agent Jason Bay.  Last month, Bay signed a four-year, $66 million deal from the Mets, with a vesting option that could kick the value up to $80 million over five years. On the other hand, Beltre signed a one-year, $9 million deal with the Boston Red Sox, with a $5 million option for a second season.

But at least Beltre has a job next year, albeit at less money than expected. On the other hand, Boras’ client Jarrod Washburn turned down a $5 million deal from the Minnesota Twins, apparently thinking he could get a better offer elsewhere. No better deal materialized, and now the free agent pitcher is reportedly considering hanging up his spikes.

True, Boras still has the top client list in baseball. And he still has considerable skills with getting some players a great payday - Boras did get $36 million for the putrid Oliver Perez, after all.  It’s also true that Boras’ bluster is as a defining characteristic for him as his reliance upon a “mystery team” to drive the price up.

Yet you would think that the agent known for his meticulous notebooks on his clients would have noticed that it’s not the 2000-2001  offseason anymore, the year where he got Alex Rodriguez a then-record $252 million deal, or even the winter of 2007, where A-Rod got another record-setting deal (albeit without Boras’ public involvement.) Instead, the worst economic conditions since the Great Depression have driven the price down for most free agents, yet Boras is still blathering about the big payday, to the detriment of some of his clients.

There’s also some of the unseemly shenanigans Boras has been linked with in recent years - from his hand in announcing during the final game of the World Series that Alex Rodriguez was opting out of his contract, to the agent appearing to orchestrate Manny Ramirez’ ugly departure from the Boston Red Sox.

While Boras is still a force to be reckoned with in baseball, the 2009 offseason hasn’t been among his better ones. He could use some big wins in the near future - and a reality check about today’s economic climate.

Photo by misschatter