5 biggest trades by Billy Beane

When Oakland Athletics general manager Billy Beane pulled the trigger on a blockbuster deal that sent third baseman Josh Donaldson to the Toronto Blue Jays in exchange for infielder Brett Lawrie and a trio of prospects, it reaffirmed that Beane is not one to shy away from a big deal.

In his 16 years at the helm in Oakland, Beane has carefully crafted a roster that has found success well beyond its means. 

Here are the five biggest trades in Beane's history in the front office in Oakland:

5. 2011 - A's trade Trevor Cahill and Craig Breslow to Diamondbacks for Jarrod Parker, Ryan Cook and Collin Cowgill

Coming off an NL West championship, the Arizona Diamondbacks bolstered their rotation by acquiring starter Trevor Cahill and left-handed reliever Craig Breslow. 

"I'd heard a lot of other guys' names bouncing around. The last couple days I never thought I'd be the first one to go," Cahill told the Associated Press.

Cahill would go 21-22 with a 3.87 ERA in his first two years in the desert but struggled in 2014, going 3-12 with a 5.61 ERA. Breslow spent part of one season in Arizona before he was shipped to the Boston Red Sox. 

Jarrod Parker made 61 starts in his first two seasons with Oakland, going 25-16 before undergoing a second Tommy John surgery that cost him all of last season. 

Ryan Cook came out of the bullpen 54 times in 2014, posting a 3.42 ERA with 50 strikeouts in as many innings, while Collin Cowgill appeared in 38 games before he was traded to the New York Mets in 2012. 

4. 2008 - A's trade Nick Swisher to White Sox for Gio Gonzalez, Ryan Sweeney and Fautino de los Santos

After a disappointing 76-win season, Beane continued the A's rebuild by shipping fan favorite and offensive leader Nick Swisher to the Chicago White Sox for three minor leaguers. Swisher slashed .262/.381/.455 with 22 home runs and 78 RBIs the season before. 

"I got off the plane from the winter meetings, I said to (assistant GM) David (Forst), 'Who are we kidding?'" Beane told the Associated Press. "We can't let hope be our strategy here. That's what we're doing. ... We can't waste another year. If this needs to be done, it needs to be done."

The top prospect in the deal was pitcher Fautino de Los Santos, who only went on to pitch 36 1/3 innings in the majors. Both Ryan Sweeney and Gio Gonzalez had productive stints with the A's. 

Sweeney hit .286/.347/.383 with 13 home runs, 80 doubles and 159 RBIs in 439 games, while Gonzalez went 38-32 with a 3.93 ERA and 511 strikeouts in 535 1/3 innings. 

3. 2007 - A's trade Dan Haren to Diamondbacks for Brett Anderson, Chris Carter, Carlos Gonzalez and three others

Three weeks prior to the Swisher trade, the A's dealt their top pitcher, Dan Haren away to the Diamondbacks for six players. 

Haren, who was coming off his first All-Star appearance, brought a slew of players that never would to develop into key pieces for Beane. 

Brett Anderson broke the A's rookie single-season strikeout record in 2009 but injuries limited him from pitching over 120 innings in four of his five major league seasons. Chris Carter slashed .214/.310/.425 with 19 home runs in 106 games before he was traded to the Houston Astros and Carlos Gonzalez appeared in 85 games before he was shipped to the Colorado Rockies. 

2. 2011 - A's trade Gio Gonzalez to Nationals for Tommy Milone, Derek Norris and two others

Having already dealt Cahill to the Diamondbacks, the A's ship Gio Gonzalez to the Washington Nationals for four prospects. 

Gonzalez was coming off his best year as a starter and earned his first All-Star appearance. The left-hander went on to win 21 games in his first season in Washington and owns a 42-26 record in three seasons since. 

Tommy Milone went 31-22 in parts of three seasons with Oakland before a loaded rotation forced him out, with the A's shipping him to the Minnesota Twins. Norris settled in behind the plate over the past three seasons and hit .246/.336/.392 with 26 home runs in 285 games. Neither A.J. Cole nor Brad Peacock ever pitcher for Oakland. 

1. 2008 - A's trade Carlos Gonzalez and Huston Street to Rockies for Matt Holliday

In what will likely go down as the worst trade on Beane's resume, the A's dealt outfielder Carlos Gonzalez and reliever Huston Street for outfielder Matt Holliday. 

Holliday appeared in just 93 games for Oakland - hitting 11 home runs - before departing for free agency and eventually signing with the St. Louis Cardinals. 

Gonzalez has spent the last six seasons with Colorado and won three Gold Gloves in addition to appearing in a pair of All-Star games. Gonzalez has hit at least 22 home runs in four of the last five seasons. 

Street emerged as a valuable piece at the back end of Colorado's bullpen, converting 84 saves and a 3.50 ERA in 170 appearances.