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2000s: The Decade in Sports
Posted: Wednesday December 9, 2009 11:07AM; Updated: Wednesday December 9, 2009 11:07AM

MLB: Trades, free agents and draft (cont.)

By Jon Heyman,

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Worst free-agent signings

Mike Hampton had two disappointing seasons with the Rockies after signing an eight-year, $120 million contract.

1. Mike Hampton, Rockies; Dec. 12, 2000
For $120 million over eight years, Hampton gave the Rockies half a good year and lot of heartache. He did not only fall precipitously but he also proved to be no joy to be around. GM Dan O'Dowd eventually extricated himself from a good part of the contract with some slick trading that eventually landed Hampton in Atlanta.

2. Carl Pavano, Yankees; Dec. 20, 2004
For $40 million over four years -- actually, $39.95 million, a distinction that would inspire Pavano to try not to pay his agent -- the Yankees got nine wins, or three fewer than Pavano had in 2009. He pitched poorly, but what's worse, he was hurt a lot, got into a notable unreported car accident and got along with almost no one.

3. Chan Ho Park, Rangers; Jan. 16, 2002
Park was an excellent starter for the Dodgers before he signed for $65 million over five years with Texas, and has reinvented himself as an effective reliever in recent years. But in between, he was an unmitigated disaster with Texas.

4. Jason Schmidt, Dodgers; Dec. 6, 2006
Despite a so-so finish with the Giants the year before his free agency that raised concerns about his arm, several teams hotly pursued Schmidt, with the Dodgers the unlucky winner. For $47 million over three years, they got almost zip.

5. Milton Bradley, Cubs; Jan. 9, 2009
Bradley's rep as a malcontent was well-known when the Cubs decided to sink $30 million over three years (technically it was $20 million guaranteed, but the third year has already vested) into a bad idea. Bradley didn't get along with his manager, teammates or fans, and what's worse, he was non-productive.

Biggest draft busts

1. Matt Bush, Padres, 1st pick, 2004
One of the all-time worst picks, the Padres passed on Justin Verlander and other obvious choices to go local (he's from San Diego) and cheap ($3 million). The first indication something was amiss came when Bush and his buddies trashed a private box at Petco Park on the first visit. Behavioral problems and a lack of hitting tanked his short-lived shortstop career. Eventually, he was converted to a pitcher. But he never made it out of the low minors.

2. Bryan Bullington, Pirates, 1st pick 2002
Pitsburgh, which is notorious for its bad drafts, took this Ball State rightahder over such notables as B.J. Upton, Prince Fielder, Scott Kazmir and Cole Hamels partly due to signability concerns (also, they frequently draft the wrong guy). Bullington has bounced around the minors, though he's gotten into major-league games with the Pirates, Indians and Blue Jays. Overall, he is 0-5 with a 5.08 ERA lifetime. Hardly worthy of a No. 1 overall pick.

3. Dewon Brazelton, Rays, 3rd pick 2001
Tampa Bay has had some notably excellent high draft choices. But this wasn't one of them. Brazelton, a star at Middle Tennessee State, was hampered by injury and flamed out of Tampa quickly. He got a fresh start with the Padres and earned a spot in their rotation in 2006, only to lose his first two starts and allow 17 earned runs in 6 1/3 innings. Brazelton is 8-25 with a 6.38 ERA in his career, including 0-16 on the road. He pitched last season with the Atlantic League's Camden Riversharks.

4. Daniel Moskos, Pirates, 4th pick, 2007
It's early yet, but Moskos looks like he'll be a situational reliever, which is something you never want from the fourth overall pick. The Pirates' decision-makers were swayed from spending a few million more on Georgia Tech catcher Matt Wieters, a call that ultimately contributed to them losing their jobs. Wieters went to the Orioles with the next pick.

5. Clint Everts, Expos, 5th pick 2002
He had the name of a ballplayer, and was from the hotbed of Houston. But unfortunately, he will forever be recalled as the pitcher who was taken one spot before the Royals got Zack Greinke.

Biggest draft steals

1. Jason Bay, Expos, 22nd round, 2000
With improved scouting, late-round steals like Mike Piazza in the 62nd round don't occur too often anymore. The All-Star rosters are populated with first- and second-rounders plus international signings, so it's rare to see an All-Star go as late as the 22nd round, as Bay did when he was plucked out of Gonzaga.

2. Ryan Howard, Phillies, 5th round, 2001
Superstars just aren't found in the fifth round anymore. But Howard was. His talent went unrealized for too long, too, as he toiled in the minor leagues for several years before instant success at the major league level. He won Rookie of the Year, MVP and has been to two World Series, winning one.

3. Ian Kinsler, Rangers, 17th round, 2003
The Diamondbacks drafted Kinsler twice, in 2000 (29th round) out of high school and 2001 (26th round) after one year at Central Arizona College. But Kinsler never signed with Arizona and eventually landed in Texas, where he has used his speed and power to become a star.

4. Kevin Youkilis, Red Sox, 8th round, 2001
He first became known as the Greek God of walks in the best-selling book Moneyball, but has gone on to great fame as a splendid hitter and versatile fielder with the Red Sox, who won a World Series with him at first base in 2007. A staple in the middle of Boston's potent lineups, he has blossomed into an intense competitor and excellent all-around player.

5. Brandon Webb, Diamondbacks, 8th round, 2000
Arizona nabbed a future ace who would win a Cy Young Award and throw at least 200 innings in five consecutive seasons before missing nearly all of 2009 with a shoulder injury.

2000s: The Decade in MLB
Posnanski: Highlights and lowlights
Posnanski: All-Decade team
Chen: 10 signature moments
Heyman: Trades, free agency and draft
POLL: Share your thoughts on the decade in MLB

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