Identifying MLB's Best Trade Deadline Dealers

In the fast-paced world we live in, sports fans have to know right away if their favorite team won or lost a trade. Things aren't always as black and white as they appear, at least initially. Only when looking back on everything can you truly say who got the better end of a deal. 

For instance, when the Indians first traded Bartolo Colon to Montreal in the summer of 2002, the outrage in Cleveland was fierce because the assumption had it just being a salary dump for a franchise that was in the early stages of a rebuilding process.

Look at that deal now: Cliff Lee, Grady Sizemore and Brandon Phillips were all sent to Cleveland in return. Even though Phillips and Lee achieved their greatest success with other organizations, that trade was a heist for the Indians. 

Now that we are able to look back at past deadline years to see how things have played out, we want to know who the best dealers in baseball have been. These are the teams that have made shrewd moves that have helped them win right away, while others were geared more towards the future. 

Our timeframe will look back at the last five years (2008-12) and ranking the winners based on a variety of factors. It's not exactly scientific, as some will be here because their moves helped them win a title and some based on wins above replacement totals for the pieces brought back. 

Note: These only include trades made on or before the non-waiver deadline July 31. 

Boston Red Sox

When the Red Sox traded for Jason Bay, it was originally seen as the deal to get Manny Ramirez out of town. Little did anyone realize that this hidden gem of a hitter was about to bring his gifts to one of the biggest franchises in all of North American sports. 

Bay thrived under the often-cruel environment of Boston, hitting .293/.370/.527 with nine home runs in 49 games for the Red Sox. He was a crucial piece to that lineup and played an integral role in getting the team to Game 7 of the ALCS against Tampa Bay. 

After a brief taste of what he could do, Bay put on a show for the Red Sox in 2009. He hit .267/.384/.537 with 36 homers, 119 RBI and 13 stolen bases, finishing seventh in the AL MVP race. 

Joining Bay on the 2009 Red Sox midway through the year was Victor Martinez, who was part of the great 2008-09 impending free agent dump the Indians went through. Like Bay, Martinez thrived in Boston by hitting .336/.405/.507 with 20 extra-base hits in 56 games. 

The Red Sox lost in the first round of the playoffs that season, getting swept by the Los Angeles Angels. But it was hardly the fault of Bay and Martinez, the latter of whom would stay in town through the 2010 season and hit .302/.351/.493 with 20 home runs. 

Even though Boston wouldn't make any major deadline moves after the 2009 season—again, last year's salary dump doesn't count since it was part of the waiver period—these two moves were enough to solidify its spot on the list. Especially when you consider that the one quality big leaguer the team gave up aside from Ramirez, who turned into a headache for the Dodgers in 2009, was Justin Masterson. 

St. Louis Cardinals

Considering where the Cardinals are at as a franchise today, with one of the best and deepest farm systems in the game and best record in the National League, it should come as no surprise to see them on this list. 

Not only have they been very successful in trades, but they do it without sacrificing a lot of talent. Obviously we don't know that at the time, though that is the fun of going back and looking at these transactions.  

The biggest move for the Cardinals came in 2009, when they acquired Matt Holliday from Oakland for Brett Wallace, Shane Peterson and Clayton Mortensen. Wallace has bounced around the big leagues and minors for the last four years, Peterson has played in two big league games and Mortensen spent two inconsistent years with Oakland before moving to Colorado. 

The Cardinals did ink Holliday to an extension in 2010, though that doesn't necessarily add anything to the trade. He has added 16.6 wins above replacement during his time in St. Louis and was part of a championship team in 2011. 

But there is more than just Holliday that puts the Cardinals here. They got the serviceable Jake Westbrook in a three-team trade with Cleveland and San Diego in 2010 while only giving up Ryan Ludwick's contract. Westbrook isn't a star but eats innings, and for a team that doesn't need a lot of help at the top of a rotation, someone who gets outs in incredibly valuable. 

In 2011, the Cardinals finally parted ways with the disappointing Colby Rasmus by trading him to Toronto in a huge three-team deal with the White Sox that netted them Edwin Jackson, Marc Rzepczynski and Corey Patterson. 

Jackson threw 78 innings in the regular season for the Cardinals and won Game 4 of the NLDS against Philadelphia by throwing six innings of five-hit, two-run ball. Rzepczynski recorded six holds and a win in the 2011 postseason. 

That same year they also acquired Rafael Furcal from the Dodgers in exchange for Alex Castellanos. Furcal has never been able to stay healthy for the Cardinals but did provide some semblance of stability at shortstop in the 2011 playoffs. 

The Cardinals are still trying to fill the void left by Furcal's inability to remain on the field, wasting a roster spot on Pete Kozma who can't hit and is a mediocre defender. 

But on the whole, when you can make trades like the one for Holliday that turns out to be incredibly lopsided and get quality pieces like Westbrook, Jackson and Furcal, all of whom played a role on a championship team, it is hard to argue with the results. 

Arizona Diamondbacks

I was actually surprised at how well the Diamondbacks have done in midseason trades lately. Not because I think they are incompetent in the front office, but they just weren't a franchise I thought of as making a lot of July trades. 

And certainly Arizona's volume of deals hasn't been as large as some teams who deal virtually every year, like the Yankees, but the quality of the deals made by the front office has been as good as any in recent years. 

The two biggest deals made both happened in 2010. It started with Dan Haren being sent to the Angels on July 25 in exchange for Joe Saunders, Patrick Corbin, Tyler Skaggs and Rafael Rodriguez. 

Saunders was just the major league piece thrown into the deal to give the Diamondbacks a starter to fill out their roster, but fast forward to today and Corbin looks like a potential top-of-the-rotation arm with a 2.35 ERA and improved stuff across the board that includes a fastball averaging 92 mph and much better off-speed pitches. 

Skaggs is still looking for the velocity he lost this season and figuring out how to pitch in the big leagues, but if/when he puts it all together, the stuff is good enough to be a No. 3 starter. 

The Diamondbacks followed that up by trading Edwin Jackson to the White Sox on July 30 in exchange for Daniel Hudson, who had a very strong year in 2011 pitching 222 innings with a 3.49 ERA and 4.8 WAR., and the now-22-year-old David Holmberg who is throwing well in Double-A. 

That second deal with the White Sox also played a key role in Arizona's 2011 postseason berth because Hudson was so good. 

Milwaukee Brewers

Looking at where the Brewers are now, last place in the National League Central with one of the worst farm systems in baseball, it is easy to criticize the work of the front office and scouting department for some poor drafts in recent years. 

But one thing you can't say is that the Brewers didn't go for it when they had a window, nor did they fail to cash in when it was clear that window had closed on them. 

Let's move all the way back to 2008 when the Brewers' run of success started. The biggest move made was to acquire CC Sabathia from Cleveland in exchange for Matt LaPorta, Zach Jackson, Rob Bryson and a player to be named later who would become Michael Brantley. 

While Brantley has turned into a solid big leaguer for the Indians, the other pieces they acquired flamed out in the big leagues. Meanwhile. Sabathia pitched masterfully in his half season with Milwaukee, putting together a 1.65 ERA, 128-25 strikeout-to-walk ratio and 255 ERA+ in 130.2 innings. He made three starts on three days rest at the end of the year to pitch the Brewers into the postseason for the first time since 1982. 

Even with Sabathia leaving for the bigger dollars offered in New York after the 2008 season, no one was going to dispute the impact he had on the Brewers in his time there. 

The Brewers also acquired Ray Durham from the Giants that same year. Taking over at second base for an injured Rickie Weeks, Durham played very well by hitting .280/.369/.477 in 41 games for the Brew Crew. All Milwaukee gave up in exchange was Darren Ford and Steve Hammond. 

That was when the Brewers' window opened, but when it closed last year they did very well to at least get something for impending free agent Zack Greinke by trading him to the Angels for Jean Segura, Johnny Hellweg and Ariel Pena. 

Segura turned into an All-Star shortstop in 2013, his first full season in the big leagues. I don't think he will be that good every year, but finding an everyday up-the-middle talent for what turned out to be a rent-a-pitcher is very good value for the Brewers. 

Plus, Hellweg has a tremendous arm and could still turn into a capable big league starter or, more likely, a very good hard-throwing reliever. Pena may never make it in The Show due to control problems, but the stuff is good enough to pitch out of a big league bullpen. 

In many ways the Brewers did exactly what a small-market team is supposed to: stock the farm system to open the window of contention, when the window hits use some of those assets to improve the big league club, and when it closes make sure to maximize the value on expiring assets. 

If only we could figure out what has gone wrong with those drafts in recent years...

Detroit Tigers

One of the great things about doing anything and everything it takes to win a championship is that you will spend money and part with any number of prospects with potential to do so. 

No team embodies that more than the Tigers, who could care less how their farm system stacks up as long as they are able to get to the postseason and compete for a World Series. That is how every franchise and fan base wishes their team operated. 

There was a long down period in Detroit in the 1990s and early 2000s, but since the middle of last decade the Tigers have been as good and consistent as any franchise in the sport. A big reason for that is their ability to hit trades, especially at the deadline, out of the park. 

The last three years have been particularly kind to the Tigers. It started in 2010, when they swapped pitcher Giovanni Soto to Cleveland for Jhonny Peralta, who the Indians really just wanted to get rid of after his inconsistent performance drove fans and the front office nuts. 

While Peralta has not found that consistent level of performance from year to year, he hit .299/.345/.478 with 21 home runs in 2011 and .301/.358/.441 with 34 extra-base hits this year and has made the All-Star team twice. 

In 2011, trying to solidify their rotation heading into the postseason, the Tigers acquired Doug Fister from Seattle. He was a solid innings eater with the Mariners, but didn't look like anything special. 

Now, Fister has turned into one of the better pitchers in the American League. He had a 57-5 strikeout-to-walk ratio in 70.1 innings with the Tigers in 2011. The last two years combined have seen him throw 288.2 innings with 291 hits allowed, 25 home runs and a 235-60 strikeout-to-walk ratio. 

All the Tigers gave up to get Fister was Casper Wells, Francisco Martinez and Charlie Furbush. Wells is no longer with the Mariners, Martinez is back with the Tigers and Furbush is a relief-only pitcher. 

Last year, when the Marlins were in the early stages of the great fire sale, the Tigers took Anibal Sanchez in exchange for Jacob Turner, who was once a top prospect but has since seen his stuff take a huge step backward, Rob Brantly, who was never a good defensive catcher and hasn't had much luck on offense, and minor league pitcher Brian Flynn. 

The Tigers also got Omar Infante in that deal to upgrade the black hole that was second base. He didn't exactly light the world on fire but provided enough defense to offset what he couldn't do with the bat. 

All stats courtesy of Baseball-Reference.com unless otherwise noted. If you want to talk baseball, feel free to hit me up on Twitter with questions or comments. 

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