I'm going to go back from the 2002 trade deadline to the 2006 trade deadline and show who's really won these trades. Chances are if I didn't cover a trade, it didn't matter. I didn't do the 2007 deadline because the jury's still out on many of the prospects who were dealt. People who matter are in bold.
Expos get Bartolo Colon and Tim Drew
Indians get Lee Stevens, Grady Sizemore, Cliff Lee, and Brandon Phillips
You have to applaud Omar Minaya for making this trade because at this point, it looks as if the Expos are going to be contracted at the end of the season. However, they gave up a great centerfielder, an above average second baseman and an enigma of a starting pitcher, along with a DH-quality first baseman. The Expos proceeded to miss the playoffs, and therefore lost this trade, which may be the single most lopsided deadline deal since Larry Andersen for Jeff Bagwell.
Cardinals get Scott Rolen and Doug Nickle
Phillies get Placido Polanco, Bud Smith, and Mike Timlin
The Phillies got a good utility infielder and a very good reliever for at that time, one of the top three third basemen in the majors. Rolen's been nicked up more and more as he's aged, but still, with a World Series in the bag with Rolen's help, they win this trade.
A's get Jose Guillen
Reds get Aaron Harang, Jeff Bruksch, and Joe Valentine
Well, Moneyball can't win every trade, and this is evidence thereof. Aaron Harang has blossomed in Cincinnati after stalling in the A's farm system, and Guillen has done his best to be a member of every AL team since that trade (going to the Angels, Mariners, and Royals since). Reds win big.
Red Sox get Jeff Suppan and Scott Sauerbeck
Pirates get Freddy Sanchez
A shortsighted trade (which happens a lot around July 31st every year), the Pirates ended up with the future NL batting champion in exchange for a journeyman starter and a mediocre lefthander.
Astros get Carlos Beltran
Athletics get Octavio Dotel
Royals get Mike Wood, John Buck, and Mark Teahen
Initially, the winner of this trade was the Astros, as Beltran caught fire and led the Astros all the way to the NLCS, where they got cut down by the Cardinals. Long term, the Royals win, because Buck has been a serviceable catcher, and Teahen has been a decent utility player, spending time at third base, first base, and in the outfield. The fact that they are the only team with players from this deal clinches the trade in their favor.
White Sox get Freddy Garcia and Ben Davis
Mariners get Mike Morse, Jeremy Reed, and Miguel Olivo
The White Sox won the World Series in 2005, in part because of Garcia's clutch pitching. Meanwhile, none of the three prospects sent back to Seattle have amounted to anything. Therefore, the White Sox won this deal.
Mets get Victor Zambrano and Bartolome Fortunado
Devil Rays get Scott Kazmir and Jose Diaz
Well, the Mets got an overachieving starter with control problems, and the Devil Rays got their staff ace. Hmm. Whoops.
Dodgers get Brad Penny, Hee Seop Choi, and Bill Murphy
Marlins get Paul Lo Duca, Guillermo Mota, and Juan Encarnacion
The Marlins ended up giving up one of the ten best starters in the National League in Brad Penny for three players that jumped ship that offseason. I'm thinking the Dodgers won that deal.
Cubs get Nomar Garciaparra and Matt Murton
Red Sox get Orlando Cabrera and Doug Mientkiewicz
Expos get Alex Gonzalez, Francis Beltran, and Brendan Harris
Twins get Justin Jones
Let's see. Red Sox win World Series, Cubs still cursed, Expos and Twins prospects don't pan out. Red Sox win... big.
Phillies get Ugueth Urbina and Ramon Martinez
Tigers get Placido Polanco
The trade itself benefitted the Tigers much more than it ever benefitted the Phillies, until you look at who replaced Polanco. Some schmoe named Utley. Still, the trade goes to the Tigers.
Yes, that's the only remotely notable trade during the 2005 season.
Nationals get Austin Kearns, Ryan Wagner, and Felipe Lopez
Reds get Bill Bray, Gary Majewski, Royce Clayton, Daryl Thompson, and Brendan Harris
The Nationals ended up with a talented corner outfielder and a super-utility player in Felipe Lopez, a player who demands playing time every day but can play anywhere on the field. Meanwhile, the Reds got two blown out bullpen arms, a decrepit shortstop, a prospect who's never shown up, and a utility player who they let get away through free agency. Advantage Washington.
Giants get Shea Hillenbrand and Vinnie Chulk
Blue Jays get Jeremy Accardo
The Giants came away from this trade with a middle reliever and a locker room cancer while the Blue Jays got a valuable set up man who showed the ability to close when BJ Ryan went down in 2007. Blue Jays win a trade that seemed irrelevant at the time.
Rangers get Carlos Lee and Nelson Cruz
Brewers get Julian Cordero, Francisco Cordero, Laynce Nix, and Kevin Mench
The Brewers dumped Lee, because he was going to become a free agent. In return, they got two prospects that didn't pan out, a closer they kept for one more season, and a player with a giant head (Mench wears the biggest hat in MLB). However, they lost this trade badly, as Cruz is the best prospect for the Rangers at this point, and seems to have 20/20 potential with a plus throwing arm.
Yankees get Bobby Abreu and Corey Lidle
Phillies get Jesus Sanchez, CJ Henry, Carlos Monasterios, and Matt Smith
The Yankees got an outfielder in Abreu who's made an offensive resurgence, and an innings eater in Lidle who died in a small plane crash. The Phillies haven't had any of the prospects they received in return pan out, so the Yankees won this deal.
Mets get Oliver Perez and Roberto Hernandez
Pirates get Xavier Nady
Both sides won in this deal, offloading underachieving players (the Mets Nady, the Pirates Perez) who regained their previous forms in their new homes.
You must remember that this just highlights what the biggest trades were, most deadline deals emphasize the "dead" part of deadline. However, this blog shows that every deadline trade is a calculated risk. You may end up parting with one of the best baseball players of a generation, like the Red Sox did with Jeff Bagwell, or you can end up stealing a player for free like the Yankees did with Bobby Abreu. It should be interesting to observe how the Braves and Rangers fare after the Saltalamacchia for Teixeira swap, and other teams on trades that we thought were meaningless.
One thing that's a constant in almost all of these trades are relief pitchers, especially those who pitch from the wrong side of the mound. If you're a team in need of fixing up your farm system, go and horde as many of them as you can on your 40-man roster in hopes of being able to dump them all at the deadline (and if you find a good one, keeping them for yourself because they're so darn hard to find).
Another thing that happens too much is teams giving up too soon on former top prospects, from the A's with Harang to the Pirates with Oliver Perez, these trades have hurt these teams now, even though the trades were made years ago.
There's a positive to these trades too. If done right, you can win your team championships, like the Cardinals did with Scott Rolen and the Red Sox with Orlando Cabrera. It's all in the gamble.