The infamous name Scott Boras has always been attached to making teams reach far deeper into their pockets to acquire what seems to be some of baseball’s finest talents. Although after the ink dries on the contracts and franchises are financially bound to a particular player for an ungodly amount of years and money, in many cases, the performance on the field tends not to live up to the figure on the paycheck.

Just look at his 100 million dollar men: Kevin Brown, Alex Rodriguez, Carlos Beltran, Barry Zito, Mark Teixeira, Matt Holliday and  Jayson Werth. Of those contracts, Brown, Zito and so far Werth have been busts for their respective clubs. Beltran was borderline given his two injury plagued seasons and underwhelming 2005 campaign. A-Rod has lived up to his contract to an extent, but with injuries mounting at age 35 and under contract for the next 6 years and $143 million, it could quickly become one of the worst deals in history. The only two $100-million dollar Boras clients to label as a good deal on both sides would be Teixeira and Holliday. You could make the argument that a number of these seven players have done well, but the obscene amount of money committed makes it difficult to say that they performed to the level they are being paid.

Of the 31 contracts I could find that have been negotiated by Boras to surpass the $30 million mark, only about 12 of them I would label as a bust. Now that is a pretty average figure, but what I found very interesting was that from 1992 to the 2006 offseason, all but two of the fifteen $30+ million dollar contracts were busts. From the winter of 2006 on, 11 of the 16 contracts have been bad contracts for the respective franchises. Is this just a matter of desperate clubs haphazardly throwing money at less-than deserving players? Or maybe Boras talking up his clients a bit too much? It could be a bit of both.

Instead of one or two large contracts being inked through Boras per year, in recent years he has negotiated 3 to 4, apparently resulting in some quantity over quality. So to answer the original question, ten to fifteen years ago Boras’ clients were worth the money, but nowadays, the players he represents seem to come with a legitimate risk. That coupled with the large amount ballclubs have to dish out to acquire his players, and the stakes become that much more higher.

With many high-end players represented by Boras such as Prince Fielder, Ryan Madson, Edwin Jackson and Carlos Pena hitting the open market this winter, it should be interesting to see if this trend continues.

It is Boras’ job to make teams want to pay top dollar for his clients, but maybe he’s just a little too good at it.