10 biggest trades in Athletics history

December 1st, 2021

OAKLAND -- The A's wheel and deal like no other. They've long sparked intrigue -- and, of course, a divergent dialogue -- with their creative choreography when it comes to roster building.

When other teams zig, as they say, the A's zag. That's been the mantra under Billy Beane's watch, but a bevy of significant trades came before him, too. Beane's mentor, Sandy Alderson, engineered a series of moves that helped the A's into the World Series. Then, there was Charlie Finley, of course. Each have left an indelible mark on the baseball landscape.

MLB.com has compiled a list of the 10 biggest trades in club history:

1. Holtzman for Monday

A's got from Cubs: LHP Ken Holtzman
A's gave up: OF Rick Monday
Date: Nov. 29, 1971

Holtzman sought a trade at the conclusion of the 1971 season and got his wish, landing in the middle of a star-studded A's rotation that also included Catfish Hunter, Vida Blue and Blue Moon Odom. Holtzman earned All-Star honors in his first two seasons with the A's and won at least 18 games in his four seasons with them, as he helped to orchestrate a string of three consecutive World Series titles ('72-74).

2. Eck

A's got from Cubs: RHP Dennis Eckersley, INF Dan Rohn
A's gave up: INF Brian Guinn, RHP Mark Leonette, OF Dave Wilder
Date: April 3, 1987

Just days before the start of the 1987 season, the A's made a history-altering trade with the Cubs, snagging Eckersley and transforming the aging starter into a Hall of Fame reliever. He revolutionized the role of the closer, tallying 320 of his 390 career saves in Oakland. He is one of just two pitchers in Major League history to have both a 20-win season ('78) and a 50-save season ('92) in his career.

3. Welch

A's got from Dodgers: RHP Bob Welch, LHP Matt Young
A's gave up: INF Alfredo Griffin, RHP Jay Howell (Dodgers); RHPs Kevin Tapani and Wally Whitehurst (Mets)
Date: Dec. 11, 1987

Then-general manager Alderson brought in Welch as part of an offseason overhaul that also included the arrivals of veterans Dave Parker and Dave Henderson. The right-hander finished his career with the A's, earning the American League Cy Young Award in 1990 following a historic 27-win season.

4. Rickey returns

A's got from Yankees: OF Rickey Henderson
A's gave up: LHP Greg Cadaret, RHP Eric Plunk, OF Luis Polonia
Date: June 21, 1989

Hesitant to re-sign Henderson to a new deal at season's end, the Yankees opted to make the speedy outfielder available at midseason in exchange for needed pitching help. They found takers in the A's -- the only team Henderson would reportedly sign off on. The hometown hero returned to Oakland and was essential to the A's postseason run that culminated in a World Series victory, hitting .474 in a four-game sweep against the Giants. The next season, he won the AL MVP Award after hitting .325 with 28 home runs, 65 stolen bases and a 1.016 OPS for the AL pennant-winning A's.

5. Mulder for Haren

A's got from Cardinals: RHPs Dan Haren and Kiko Calero, INF
A's gave up: LHP Mark Mulder
Date: Dec. 18, 2004

In a span of just three days, the A's parted ways with two members of their Big Three -- first shipping Tim Hudson to Atlanta, and soon after trading Mulder in a surprise deal for a young pitching prospect in Haren, plus more -- including an underrated Calero, who did fine work in green and gold. Haren went on to establish himself among the game's best. He made 102 starts over three full seasons with the A's and was an integral part of their 2006 playoff club that reached the AL Championship Series.

6. Haren for CarGo and Co.

A's got from D-backs: LHPs , and Greg Smith, OFs and Aaron Cunningham, INF Chris Carter
A's gave up: RHPs Dan Haren and Connor Robertson
Date: Dec. 14, 2007

Beane did well here, flipping Haren for a massive haul that simultaneously featured controllable young talent and significant trade bait for the future. All six players acquired played for the A's, though many were later dealt to continue a theme of Beane's workings. His web of trades have allowed him to creatively construct winning rosters with limited resources.

7. Donaldson Part I

A's got from Cubs: C Josh Donaldson, RHP Sean Gallagher, OFs Matt Murton and Eric Patterson
A's gave up: RHPs Rich Harden and
Date: July 8, 2008

Let's start here before approaching the elephant in the room. It's important to remember that Donaldson once represented one of Beane's biggest coups. The then-22-year-old catching prospect would debut to little fanfare two years later. Then, of course, 2013 changed everything. Following a shift to third base, Donaldson seemingly came out of nowhere to hit .301/.384/.499 with 24 homers and 93 RBIs -- the first of a string of superb seasons as he began his climb to superstardom.

8. CarGo, Street for Holliday

A's got from Rockies: OF
A's gave up: OF Carlos Gonzalez, RHP , LHP Greg Smith
Date: Nov. 10, 2008

So began a rocky marriage that lasted just 93 games. Holliday's disdain for Oakland is well documented -- he even singled out the A's in his no-trade clause when he later signed with the Yankees -- and A's fans never warmed to him, either. He was subsequently shipped off to St. Louis, while Gonzalez blossomed into one of the game's best players and Street continued his dominance as a closer.

9. Cespedes for Lester

A's got from Red Sox: LHP , OF Jonny Gomes
A's gave up: OF
Date: July 31, 2014

Beane has a knack for surprising, but he absolutely stunned with this megadeal, sacrificing his stud outfielder in Cespedes for an established big-time pitching performer in Lester -- just weeks after acquiring another proven starter, Jeff Samardzija, from the Cubs in another blockbuster. This left little doubt that Beane was all-in for a run at October. The script, of course, didn't go as planned: The A's stumbled down the stretch and barely made it into the AL Wild Card Game. Lester allowed six earned runs in 7 1/3 innings in the topsy-turvy, 12-inning affair that ended in a heartbreaking A's loss. But Beane maintains the A's would have missed out on the playoffs entirely without Lester, who pitched to a 2.35 ERA in 11 regular-season starts for Oakland. Lester became a free agent, while Boston traded Cespedes to Detroit during the offseason.

10. Donaldson Part II

A's got from Blue Jays: RHP , LHP , INFs Brett Lawrie and
A's gave up: INF Josh Donaldson
Date: Nov. 28, 2014

Donaldson's time in the A's organization ended abruptly in the winter of 2014, sending shockwaves throughout the baseball community and depressing hordes of Oakland fans. Beane saw an opportunity to give up his best player for a stream of talent, and it's still too early to declare the winner of this deal. While Donaldson earned AL MVP honors with the Blue Jays in 2015, the A's hope to see a similar ascent toward stardom from Barreto.