1. Alex Rodriguez to the Yankees from the Rangers for Alfonso Soriano and Joaquin Arias; Feb. 16, 2004Rodriguez was being pursued by the Red Sox all during the winter of 2003-04. And he probably would have gone to Boston had the players union signed off on a trade that would have diminished the value of his record $252 million contract by a few million. But when all hope seemed lost, out of the blue came the blockbuster deal to the rival Yankees, the team that was truly made for baseball's biggest and best-paid star.
The door was opened for A-Rod when 2003 playoff hero Aaron Boone, the Yankees' third baseman at the time, injured his knee in a pickup basketball game. When A-Rod, anxious to leave Texas, was asked whether he would considering switching from shortstop to third base, he didn't hesitate. Rangers owner Tom Hicks, equally anxious to get out from under the contract (or at least most of it), agreed to pay $9 million per year to the Yankees and send Rodriguez to New York for Soriano and shortstop prospect Arias.
2. Josh Beckett, Mike Lowell and Guillermo Mota to the Red Sox from the Marlins for Hanley Ramirez, Anibal Sanchez, Jesus Delgado and Harvey Garcia; Nov. 24, 2005Boston wanted to add an ace to the top of its rotation while the Marlins were looking to supplement their supply of young talent while cutting payroll. The big deal was engineered while Red Sox GM Theo Epstein was on hiatus following an impasse in negotiations to bring him back, and while it benefited both teams -- Beckett and Lowell became key players in Boston's second World Series win and the Marlins got their franchise player in Ramirez -- Epstein has spent some time since returning trying to reacquire Ramirez, one of the best young players in baseball.
Beckett has delivered for Boston in much the same way he brought a championship to Florida, following decent regular seasons with exceptional postseason performances. He has been the ace that the Red Sox sought. Florida wanted Lowell gone in a cost-cutting purge, but he has turned out to be a much better performer in Boston than folks imagined after a slump-ridden season in Miami. Ramirez is everything Florida could have wanted, and more.
3. Curt Schilling to the Red Sox from the Diamondbacks for Brandon Lyon and Casey Fossum; Nov. 28, 2003Epstein engineered the deal by convincing Schilling that Boston would be the perfect spot for him, and winning his approval. Then he sent overrated young left-hander Fossum and reliever Lyon to Arizona in what can only be described as a steal. Schilling helped win two World Series in Boston, one with a bloody sock.
4. Manny Ramirez to the Dodgers, Jason Bay to the Red Sox, prospects Andy LaRoche, Bryan Morris, Brandon Moss and Craig Hansen to the Pirates; July 31, 2008Ramirez earned his way out by misbehaving in his final season in Boston, when the Red Sox became desperate to unload the great hitting star. Epstein arranged the three-way trade that sent Ramirez to Los Angeles, with Jason Bay coming to Boston and Pittsburgh getting four less-then-overwhelming prospects. Ramirez became an immediate sensation in L.A., where it was practically love at first sight for inhabitants of Mannywood. Ramirez helped lead the Dodgers to the NLCS, fitting into that scene much better before being caught in a drug suspension early in 2009. Bay has played well in Boston, putting up decent numbers. It's too early to judge Pittsburgh's side of things, but so far it doesn't look pretty.
5. Bartolo Colon and Tim Drew to the Expos from the Indians for Cliff Lee, Grady Sizemore, Brandon Phillips and Lee Stevens; June 27, 2002Under the impression that his franchise was going to be contracted, then-Expos GM Omar Minaya traded Montreal's three best prospects (Lee, Sizemore and Phillips) for Colon, a top-of-the-rotation starter who was going to give Montreal a shot at final glory. Montreal didn't come close to making the playoffs, and this deal became the cautionary tale for anyone thinking of trading top prospects. While Phillips, considered the best of the minor leaguers, took longer than expected to develop and didn't actually become a star until going to Cincinnati in 2006, Sizemore and Lee became sensations for the Indians. Sizemore is considered one of the best center fielders in baseball, while Lee, who led the Phillies to the World Series this year after being acquired in July, is an ace with a Cy Young Award on his résumé.
1. David Ortiz, Red Sox; Jan. 22, 2003The Red Sox thought they were getting a part-time player when they spent $1 million on Ortiz, who had been released by the Twins, a team that rarely made a mistake. Nobody thought much of Ortiz at the time, but 259 home runs later --many of them huge ones -- he proved to be a clutch middle-of-the-order slugger.
2. Manny Ramirez, Red Sox; Dec. 19, 2000The ending was bad, but Ramirez was a terrific for seven years, everything that then-GM Dan Duquette could have imagined when he spent $160 million for eight years on Cleveland's mercurial star. Ramirez's legend as a hitting savant and all-around goofball was built in Boston.
3. Ichiro, Mariners; Nov. 30, 2000A decade after the Mariners got one of the world's great all-around players, he is still a major star. Nine years of 200-plus hits makes him one of the all-time bargains. He originally cost Seattle $13.125 million for the posting fee plus $14 million for a three-year contract.
4. CC Sabathia, Yankees; Dec. 20, 2008It's only one year into an eight-year, $161 million contract, but so far Sabathia is everything the Yankees could have hoped for: a bona fide ace, a horse and a big-game pitcher who helped deliver a championship in his first season in the Bronx. The price was high, but he is worth it.
5. Chris Carpenter, Cardinals; Dec. 13, 2002St. Louis got him for a song (one year, $300,000, plus a club option for 2004), and Carpenter has been one of the game's best pitchers. He is 68-24, has two Comeback Player of the Year awards and a Cy Young since arriving from Toronto as a talented yet injury-prone pitcher. He has missed a lot of starts with assorted pains, but when healthy he has been terrific.
1. Mike Hampton, Rockies; Dec. 12, 2000For $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, 2004For $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, 2002Park 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, 2006Despite 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, 2009Bradley'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.
1. Matt Bush, Padres, 1st pick, 2004One 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 2002Pitsburgh, 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 2001Tampa 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, 2007It'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 2002He 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.
1. Jason Bay, Expos, 22nd round, 2000With 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, 2001Superstars 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, 2003The 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, 2001He 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, 2000Arizona 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.