Ranking MLB's 20 Biggest Offseason Trade Fleeces of All Time

The MLB offseason is a time when teams evaluate their rosters and look to improve for the upcoming season.

When it comes to trades, the best deals are those that help both teams get better.

Ideally, you know your players best and have done the proper evaluation to know that you are not giving up a future All-Star who might help you down the road. Dealing from a position of strength is always the best option.

Sometimes, though, a trade backfires on you and the other team walks away the undisputed winner of the deal.

No team ever wants to be the one that gets fleeced on a deal, but as history has shown us, it certainly does happen from time to time.

20. Twins Trade A.J. Pierzynski for Francisco Liriano, Joe Nathan & Boof Bonser

November 13, 2003

The Trade

Twins Receive: Francisco Liriano, Boof Bonser and Joe Nathan

Giants Receive: A.J. Pierzynski and cash 

The Winner

The Twins are the obvious winner in this trade. A.J. Pierzynski played only a single season in San Francisco and was considered a clubhouse cancer with the team.

The Twins, on the other hand, still have Francisco Liriano and Joe Nathan on their roster nearly eight years later.

Liriano finished third in Rookie of the Year voting in 2006 and was named to the All-Star team. He also finished 11th in Cy Young voting in 2010 and threw a no-hitter this season.

Nathan is a four-time All-Star who finished in the top five in Cy Young voting twice and finished in the top 20 in MVP voting twice.

19. Twins Acquire Johan Santana from Marlins for Jared Camp

December 13, 1999

The Trade

Twins Receive: Johan Santana and cash

Marlins Receive: Jared Camp 

The Winner

Do I really need to ask this question? Have you seriously ever heard of Jared Camp?

Well, Camp played in the minor leagues from 1995 to 2002 and never pitched a single inning of Major League Baseball for the Florida Marlins.

The Twins, on the other hand, received a two-time Cy Young winner who also finished in the top 10 in Cy Young voting another three times and represented them in three All-Star games.

To make matters worse, the Marlins included cash along with Santana in exchange for Camp.

18. Rockies Acquire Carlos Gonzalez and Huston Street from A's for Matt Holliday

November 11, 2008

The Trade

Rockies Receive: Carlos Gonzalez, Huston Street and Greg Smith

Athletics Receive: Matt Holliday 

The Winner

In only his second season with the Colorado Rockies, Carlos Gonzalez made Rockies fans forget about Matt Holliday. He won a Silver Slugger and a Gold Glove award and finished third in MVP voting while winning a batting title.

Huston Street has saved 84 games for Colorado following the trade and posted a 3.50 ERA.

And the Athletics' experience with Matt Holliday? Well, he underwhelmed for a half season in which he looked totally disinterested in being in Oakland. He was traded midseason for Brett Wallace, who was later traded for Michael Taylor (who has yet to make an impact with the A's).

A's fans wish CarGo was still playing center field wearing green and gold.

17. Cardinals Acquire Ozzie Smith for Garry Templeton in Six-Player Trade

December 10, 1981

The Trade

Cardinals Receive: Ozzie Smith, Steve Mura and Al Olmsted

Padres Receive: Garry Templeton, Sixto Lezcano and Luis DeLeon

The Winner

Garry Templeton would go on to play 10 seasons for the San Diego Padres following his trade from the Cardinals. He batted .252 and hit 43 homers during his time with San Diego and appeared in one All-Star game.

Ozzie Smith, on the other hand, went on to play 15 years for the Cardinals on the way to a Hall of Fame career and the distinction of being considered the greatest defensive shortstop of all time. He has the 13 Gold Gloves to prove it.

He batted .272 with 27 homers in his time with the Cardinals and represented them in 15 All-Star games.

I'd say the Cardinals got the better end of this deal.

16. Phillies Acquire Bobby Abreu from Devil Rays for Kevin Stocker

November 18, 1997

The Trade

Phillies Receive: Bobby Abreu

Devil Rays Receive: Kevin Stocker 

The Winner

Kevin Stocker played a little over two-and-a-half seasons with the Tampa Bay Devil Rays and batted .250 with nine homers.

Bobby Abreu would play nine seasons with the Philadelphia Phillies, batting .303 with 195 homers, two All-Star game selections and a Gold Glove.

Abreu never even played a single game for the Devil Rays before his trade. He was selected with the sixth pick of the expansion draft and then dealt to Philadelphia in exchange for Stocker.

15. Expos Acquire Pedro Martinez from Dodgers for Delino DeShields

November 19, 1993

The Trade

Expos Receive: Pedro Martinez

Dodgers Receive: Delino DeShields 

The Winner

Delino DeShields played three seasons with the Dodgers following his trade from the Montreal Expos. He batted .241 with 15 homers and 114 stolen bases with Los Angeles.

The player he was traded for, Pedro Martinez, went on to pitch four seasons for the Montreal Expos and win his first Cy Young Award.

Pedro would finish his tenure with the Expos with a 55-33 record, 3.06 ERA and 843 strikeouts. He also appeared in a pair of All-Star games.

I think we have to give the Expos the win in this trade.

14. Cubs Acquire Ryne Sandberg and Larry Bowa from Phillies for Ivan de Jesus

January 27, 1982

The Trade

Cubs Receive: Ryne Sandberg and Larry Bowa 

Phillies Receive: Ivan de Jesus 

The Winner

Ivan de Jesus was a good player at the time of this trade, but not nearly as great as Ryne Sandberg would become for the Cubs.

Sandberg batted .285 for Chicago during his Hall of Fame career and added 282 home runs. He was named to 10 All-Star games and won an MVP award, nine Gold Glove awards and seven Silver Slugger awards.

Not a bad deal for the Cubs. A rather forgettable trade for the Phillies, though.

13. Phillies Acquire Steve Carlton from Cardinals for Rick Wise

February 25, 1972

The Trade

Phillies Receive: Steve Carlton

Cardinals Receive: Rick Wise 

The Winner

Following his trade from Philadelphia to St. Louis, Rick Wise would pitch two seasons with the Phillies and win 16 games in both seasons. His final pitching line for the Cardinals included a 32-28 record and 3.24 ERA.

Steve Carlton, on the other hand, would win 27 games in his first season with the Phillies and become one of the most dominant pitchers of the '70s.

He pitched a total of 15 seasons with the Phillies and had a 241-161 record and 3.09 ERA. He also won four Cy Young awards, appeared in seven All-Star games and won a Gold Glove award.

The Phillies fleeced the Cardinals on this one!

12. Padres Acquire Adrian Gonzalez and Chris Young from Rangers

January 6, 2006

The Trade

Padres Receive: Adrian Gonzalez, Chris Young and Terrmel Sledge

Rangers Receive: Adam Eaton, Akinori Otsuka and Billy Killian

The Winner

Adam Eaton pitched a single season with Texas, posting a 7-4 record and 5.12 ERA.

Akinori Otsuka pitched two seasons for the Rangers, making 97 appearances and posting a 2.25 ERA before retiring.

Chris Young would go on to a 33-25 record and 3.60 ERA for the San Diego Padres, and Adrian Gonzalez would become one of the best hitters in baseball.

Gonzalez hit .288 and connected for 161 homers on his way to three All-Star appearances and a pair of Gold Glove awards.

11. Cubs Acquire Derrek Lee from Marlins for Hee-Seop Choi

November 25, 2003

The Trade

Cubs Receive: Derrek Lee

Marlins Receive: Hee-Seop Choi and Mike Nannini 

The Winner

Hee-Seop Choi wound up playing just a half season for the Florida Marlins following his trade from the Cubs in exchange for Derrek Lee.

Lee went on to play seven seasons for the Chicago Cubs and batted .298 with 179 homers, two All-Star game appearances and a pair of Gold Glove awards.

The Cubs got the better end of this deal.

10. New York Yankees Acquire Roger Maris from A's in Seven-Player Swap

December 11, 1959

The Trade

Yankees Receive: Roger Maris, Joe DeMaestri and Kent Hadley

Athletics Receive: Marv Throneberry, Norm Siebern, Don Larsen and Hank Bauer

The Winner

Don Larsen pitched just one season for the Athletics, going 1-10 with a 5.38 ERA. Hank Bauer played a total of 138 games over two seasons and batted .271. Marv Throneberry played one-and-a-half seasons, batting .246, and Norm Siebern played four seasons with the Athletics and batted .289 with 78 homers.

All you need to know about the Yankees' side of the trade though, is that Roger Maris would go on to win back-to-back MVP awards immediately following the trade and set the single-season home run record with 61 homers in 1961.

The other two players were really just a bonus after Maris' performance.

9. Dodgers Acquire Andre Ethier from A's for Milton Bradley

December 13, 2005

The Trade

Dodgers Receive: Andre Ethier

Athletics Receive: Milton Bradley and Antonio Perez

The Winner

The A's did reach the American League Championship Series with Milton Bradley on the roster immediately following this trade, but his actual contribution is a matter of debate amongst A's fans. He was shipped out of town in the middle of the next season.

Andre Ethier has played six seasons for the Los Angeles Dodgers, appeared in two All-Star games, won a Silver Slugger award and finished in the top 10 in MVP voting once.

Ethier is still in his prime and has a chance to become one of the top young outfielders in baseball.

The Dodgers certainly got the better end of this deal.

8. Cubs Acquire Sammy Sosa from White Sox for George Bell

March 30, 1992

The Trade

Cubs Receive: Sammy Sosa and Ken Patterson

White Sox Receive: George Bell

The Winner

George Bell was on the downside of his career when this trade took place. He played two seasons with the White Sox before retiring, putting together a .240 batting average.

Sammy Sosa was still just 23 years old at the time of the trade and would go on to become one of the most dominant power hitters ever during his 13 seasons with the Cubs.

He hit .284 and connected for 545 homers while wearing a Cubs uniform.

Steroid use or not, the Cubs definitely got the better end of this trade.

7. Cincinnati Reds Acquire Joe Morgan from Astros in Eight-Player Trade

November 29, 1971

The Trade

Reds Receive: Joe Morgan, Ed Armbrister, Jack Billingham, Cesar Geronimo and Denis Menke

Astros Receive: Tommy Helms, Lee May and Jimmy Stewart

The Winner

Tommy Helms played four seasons for the Astros and batted .269. Lee May played three seasons for the Astros and put up good numbers. He batted .274 and hit 81 homers for Houston. Jimmy Stewart was pretty much a non-factor.

Joe Morgan went on to a Hall of Fame career with the Reds, though. He batted .288 and hit 152 homers along with his 1,155 hits in a Reds uniform. He also won a pair of World Series championships as a key member of the Big Red Machine.

6. Toronto Blue Jays Acquire Fred McGriff from Yankees in Five-Player Swap

December 9, 1982

The Trade

Blue Jays Receive: Fred McGriff, Dave Collins, Mike Morgan and cash

Yankees Receive: Tom Dodd and Dale Murray

The Winner

The only details of this trade worth knowing are that Fred McGriff would go on to play five seasons for the Toronto Blue Jays, while Tom Dodd would never play a game for the Yankees and Dale Murray was less than stellar.

McGriff batted .278 and hit 125 homers along with receiving MVP votes in three seasons and winning a Silver Slugger award with Toronto.

5. Chicago Cubs Acquire Ferguson Jenkins from Phillies in Five-Player Trade

April 21, 1966

The Trade

Cubs Receive: Ferguson Jenkins, John Herrnstein and Adolfo Phillips

Phillies Receive: Bob Buhl and Larry Jackson 

The Winner

Bob Buhl was on the downside of his career at the time of this trade. He would pitch just a year and a half for the Phillies following the trade, and his stats were less than impressive with just a 4.93 ERA.

Larry Jackson was better in his time with Philadelphia, compiling a 41-45 record and a 2.95 ERA.

Fergie Jenkins, on the other hand, went on to a Hall of Fame career.

He pitched two stints with the Cubs. During his first stint, following the trade, he appeared in three All-Star games, won a Cy Young Award and received Cy Young votes in three additional seasons.

4. California Angels Acquire Nolan Ryan, Three Players from Mets for Jim Fregosi

December 10, 1971

The Trade

Angels Receive: Nolan Ryan, Don Rose, Frank Estrada and Leroy Stanton

Mets Receive: Jim Fregosi 

The Winner

Jim Fregosi played in 146 games over a season and a half with the Mets following his trade from the California Angels. He managed a .233 batting average playing in New York.

Among the package of players he was traded for was a young pitcher named Nolan Ryan.

Ryan would go on to become one of the most dominant pitchers in baseball history. Ryan compiled a 138-121 record, 3.07 ERA and 2,416 of his record 5,714 career strikeouts with the Angels.

Undervaluing a future Hall of Famer is no way to win a trade, as we've seen repeatedly throughout this slideshow.

3. Baltimore Orioles Acquire Frank Robinson from Reds for Three Players

December 9, 1965

The Trade

Orioles Receive: Frank Robinson

Reds Receive: Milt Pappas, Jack Baldschun and Dick Simpson

The Winner

Milt Pappas had a winning record, 30-29, and a 4.04 ERA for the Reds following his trade from the Orioles. Jack Baldschun was less impressive at 1-5 with a 5.25 ERA, and Dick Simpson batted just .246 during his two seasons in Cincinnati.

The player the Reds gave up, Frank Robinson, proved he still had plenty of productive years left. He appeared in five All-Star games, won an MVP award and batted .300 with 179 homers in his six seasons with the Orioles.

He was already headed towards induction into Cooperstown based on his career with the Reds, but he solidified his place in history with the Orioles.

2. New York Giants Acquire Christy Mathewson from Reds for Amos Rusie

December 15, 1900

The Trade

Giants Receive: Christy Mathewson

Reds Receive: Amos Rusie

The Winner

This trade ultimately wound up being a swap of Hall of Famers.

It was also a total fleecing by the New York Giants, though.

Amos Rusie was at the end of his career at the time of his trade and made just three starts for the Reds following the swap. His record wound up 0-1 with a 8.59 ERA.

Christy Mathewson, just 20 years old at the time of the trade and pitching in the minor leagues, went on to win 372 games for the Giants and maintain a 2.12 ERA. He led the league in strikeouts and ERA five times each.

1. Babe Ruth Sold to New York Yankees for $100,000 from Boston Red Sox

January 3, 1920

The Trade

Yankees Receive: Babe Ruth

Red Sox Receive: $100,000 

The Winner

No debating this one.

The Red Sox would wind up with an 86-year championship drought following the sale of Babe Ruth to the New York Yankees.

The Yankees would go on win more World Series than any other team in baseball history during that same span, and Ruth would go down as the greatest player to ever put on a uniform.

Ruth had a .349 batting average and hit 659 home runs over a 15-year career in New York.

No player before or after has been as dominant as Ruth was for the Yankees.