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The magic of Scott Boras: 10 of the agent's most notorious deals

David Brown
Big League Stew

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'Twas the week before Major League Baseball's winter meetings and all through the house, GMs could hear Scott Boras squeezing down the chimney in search of yet another series of big paydays.

Boras, the agent nobody wants to haggle with, is noted for creative and aggressive negotiations that sometimes lead to acrimony, holdouts and, usually, big raises for his clients — a list of which is available here, at MLB Trade Rumors.

Here are the 10 most-outrageous deals ever negotiated by Boras:

10. Adrian Beltre, Seattle Mariners: 5 years, $64 million. A solid player with the bat, an above-average defensive player, just overpaid for what he has produced since 2005. A lot of light shines on this deal because it came a day after the M's signed Richie "Depth Perception" Sexson for $50 million. That, and the M's hoped they were getting a guy who would hit 40 homers every season, like when Beltre hit 48 in 2004. Sadly for the saps in Seattle, these deals helped seal the M's fate for a decade.

9. Daisuke Matsuzaka, Boston Red Sox: 6 years, $52 million. Signed before the 2007 season, Dice-K's price is actually nearly double what you see above because of the $51,111,111.11 "posting fee" that Boston paid Nippon Professional Baseball just for the right to negotiate with Boras. They'll pay a little over $17 million per season for Dice, who so far is 33-15 with a 3.72 ERA and a share of a World Series title. Plus, he comes with that great winter coat!

8. Kevin Millwood, Texas Rangers: 5 years, $60 million. Won 16 games and had a 4.52 ERA in 34 starts in '06, but has been bad, brittle or both ever since. Gave up 220 hits in 168 innings last year. Needs to pitch at least 180 innings this season for his 2010 season to be picked up.

7. Carlos Beltran, New York Mets: 7 years, $119 million. Boras parlayed Beltran's ridiculous 2004 postseason for the Houston Astros (20-for-46, eight homers, 14 RBIs, 21 runs scored) into what, by 2008, was the richest annual deal in the NL.

6. Kevin Brown, Los Angeles Dodgers: 7 years, $105 million. James Kevin Brown, a right-handed pitcher. A man who never won a Cy Young and was turning 34 years old before the 1999 season. Gentleman, we can rebuild his contract. We have the leverage, and Dodgers general manager Kevin Malone is a sucker. We have the capability to make the world's first $100 million baseball player. Kevin Brown will be that man. Richer than he was before. Richer, richer, richer. Despite a bionic contract, Brown broke down 2 1/2 years into the deal without leading the Dodgers to the playoffs and was out of baseball by the time the contract expired.

5. Matt White, Tampa Bay Devil Rays: $10.2 million bonus. Who? White was the seventh overall pick in the 1996 draft, but he became a free agent (along with Travis Lee, John Patterson and Bobby Seay) after Boras found a loophole in the draft rules. Dang lawyers! White went 35-47 with a 4.65 ERA in 122 minor-league appearances, which appeared to cease happening in 2003. He never made the bigs, but he still played a key role in the escalation of salaries.

4. Andruw Jones, Los Angeles Dodgers: 2 years, $36.2 million. After finishing a $75-million deal with the Braves, Jones fled to the West Coast and had an awful 2008 in which he was out of shape, injured and bad (.158/.256/.249) in 75 games. He made a little over $548,000 per hit, with still one year to go!

3. Chan Ho Park, Texas Rangers: 5 years, $65 million. Starting in 2002, a year after breaking four or five banks on Alex Rodriguez, Rangers owner Tom Hicks paid for 22 wins (just a shade unde $3 million per victory). Park never had an ERA lower than 5.46 in 3 1/2 seasons in Arlington.

2. Barry Zito, San Francisco Giants: 7 years, $126 million. The most expensive pitcher in baseball for at least a few more hours, Zito in 2007 and '08 went 21-30 with a 4.83 ERA. His WHIPs have been 1.347 and 1.600. His K/BB ratio last year was 120/102. He also went 3-11 with a 5.93 ERA at home. But he does look good in those jeans.

1. Alex Rodriguez, Texas Rangers: 10 years, $252 million. Still the mother of all outrageous contracts, even if he's "worth it." Boras put his own special stamp on the proceedings by getting Hicks into a position where he was bidding against himself. Where it gets strange is that A-Rod topped his own record-breaker before the '08 season by negotiating a 10-year, $275 million extension with the Yanks (sans Boras).

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