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baseball The Worst MLB Free Agent Signings of All Time  

PhilWa
2.5k votes 256 voters 3.8k views

List Rules This list also includes trade acquisitions and subsequent large contracts.

Can you think of big name free agent signings in baseball that have proven to be terrible. What are the worst of all time?
list ordered by

1
87 23
Josh Hamilton is listed (or ranked) 1 on the list The Worst MLB Free Agent Signings of All Time
Josh Hamilton Outfielder, Left fielder, Center fielder - 5 years, $125 million, Los Angeles Angels

2
86 23
Carl Crawford is listed (or ranked) 2 on the list The Worst MLB Free Agent Signings of All Time
Carl Crawford Left fielder - 7 years, $142 million, Boston Red Sox

3
79 20
Bobby Bonilla is listed (or ranked) 3 on the list The Worst MLB Free Agent Signings of All Time
Bobby Bonilla Right fielder, Outfielder, Third baseman - Still owed $30 million by the Mets through 2035

4
90 27
Mike Hampton is listed (or ranked) 4 on the list The Worst MLB Free Agent Signings of All Time
Mike Hampton Starting pitcher, Pitcher - 8 years, $121 million, Colorado Rockies

5
73 21
Jason Bay is listed (or ranked) 5 on the list The Worst MLB Free Agent Signings of All Time
Jason Bay Left fielder - 4 years, $66 million, New York Mets

6
84 28
Barry Zito is listed (or ranked) 6 on the list The Worst MLB Free Agent Signings of All Time
Barry Zito Starting pitcher, Pitcher - 7 years, $126 million, San Francisco Giants

7
67 19
B. J. Upton is listed (or ranked) 7 on the list The Worst MLB Free Agent Signings of All Time
B. J. Upton Center fielder - 4 years, $60 million, Atlanta Braves

8
108 49
Alex Rodriguez is listed (or ranked) 8 on the list The Worst MLB Free Agent Signings of All Time
Alex Rodriguez Shortstop, Third baseman - 10 years, $250 million, Texas Rangers and 10 years $275 million with the New York Yankees.

9
71 25
Mo Vaughn is listed (or ranked) 9 on the list The Worst MLB Free Agent Signings of All Time
Mo Vaughn First baseman - 6 years, $80 million, Anaheim Angels

10
55 18
Dan Uggla is listed (or ranked) 10 on the list The Worst MLB Free Agent Signings of All Time
Dan Uggla Second baseman - 5 years, $62 million, Atlanta Braves

11
49 16
Gary Matthews, Jr. is listed (or ranked) 11 on the list The Worst MLB Free Agent Signings of All Time
nathaniel.freiberg added Gary Matthews, Jr. Outfielder, Center fielder - 5 years, $50 million, Los Angeles Angels of Anaheim

12
67 31
Alfonso Soriano is listed (or ranked) 12 on the list The Worst MLB Free Agent Signings of All Time
Alfonso Soriano Left fielder, Second baseman - 8 years, $136 million, Chicago Cubs

13
8 0
Pablo Sandoval is listed (or ranked) 13 on the list The Worst MLB Free Agent Signings of All Time
mal3607 added Pablo Sandoval First baseman, Third baseman

14
46 21
Kevin Brown is listed (or ranked) 14 on the list The Worst MLB Free Agent Signings of All Time
Kevin Brown Pitcher - 7 years, $105 million, Los Angeles Dodgers

The Best MLB Managers of All Time

15
49 25
Jacoby Ellsbury is listed (or ranked) 15 on the list The Worst MLB Free Agent Signings of All Time
Jacoby Ellsbury Center fielder - 7 years, $153 million, New York Yankees

16
70 45
Albert Pujols is listed (or ranked) 16 on the list The Worst MLB Free Agent Signings of All Time
Albert Pujols First baseman - 10 years, $240 million, Los Angeles Angels

17
43 23
Albert Belle is listed (or ranked) 17 on the list The Worst MLB Free Agent Signings of All Time
Albert Belle Outfielder, Left fielder - 5 years, $65 million, Baltimore Orioles

18
19 4
Shin-Soo Choo is listed (or ranked) 18 on the list The Worst MLB Free Agent Signings of All Time
DanielHanley added Shin-Soo Choo Right fielder, Outfielder, Center fielder

19
41 23
Richie Sexson is listed (or ranked) 19 on the list The Worst MLB Free Agent Signings of All Time
Richie Sexson First baseman - 4 years, $50 million, Seattle Mariners

20
37 20
Juan Pierre is listed (or ranked) 20 on the list The Worst MLB Free Agent Signings of All Time
Juan Pierre Outfielder, Left fielder - 5 years, $45 million, Los Angeles Dodgers

21
46 29
Prince Fielder is listed (or ranked) 21 on the list The Worst MLB Free Agent Signings of All Time
Prince Fielder First baseman - 9 years, $214 million, Detroit Tigers

The Greatest Catchers of All Time

22
42 27
Johan Santana is listed (or ranked) 22 on the list The Worst MLB Free Agent Signings of All Time
Johan Santana Starting pitcher, Pitcher - 6 years, $137 million, New York Mets

23
40 27
Jonathan Papelbon is listed (or ranked) 23 on the list The Worst MLB Free Agent Signings of All Time
Jonathan Papelbon Pitcher - 4 years, $50 million, Philadelphia Phillies

24
35 23
Adam Dunn is listed (or ranked) 24 on the list The Worst MLB Free Agent Signings of All Time
Adam Dunn Designated hitter, Outfielder, First baseman - 4 years, $56 million, Chicago White Sox

25
14 4
Jason Schmidt is listed (or ranked) 25 on the list The Worst MLB Free Agent Signings of All Time
Statmeister added Jason Schmidt Starting pitcher, Pitcher

26
40 34
Mark Teixeira is listed (or ranked) 26 on the list The Worst MLB Free Agent Signings of All Time
Mark Teixeira First baseman - 8 years, $180 million, New York Yankees

27
52 48
Robinson Canó is listed (or ranked) 27 on the list The Worst MLB Free Agent Signings of All Time
Robinson Canó Second baseman - 10 years, $240 million, Seattle Mariners

28
24 20
Matt Kemp is listed (or ranked) 28 on the list The Worst MLB Free Agent Signings of All Time
galenandrews added Matt Kemp Right fielder, Center fielder - 8 years $160 Million by LA Dodgers.

The Best MLB Seasons Without A World Series Win

29
11 8
Darryl Strawberry is listed (or ranked) 29 on the list The Worst MLB Free Agent Signings of All Time
silentdasher added Darryl Strawberry Right fielder, Outfielder

30
32 30
Jayson Werth is listed (or ranked) 30 on the list The Worst MLB Free Agent Signings of All Time
Jayson Werth Right fielder - 7 years, $126 million, Washington Nationals

31
31 30
Carlos Beltrán is listed (or ranked) 31 on the list The Worst MLB Free Agent Signings of All Time
Carlos Beltrán Right fielder, Outfielder, Center fielder - 7 years, $119 million, New York Mets

32
7 5
Don Stanhouse is listed (or ranked) 32 on the list The Worst MLB Free Agent Signings of All Time
silentdasher added Don Stanhouse Pitcher

33
4 2
Jason Heyward is listed (or ranked) 33 on the list The Worst MLB Free Agent Signings of All Time
TRENT13 added Jason Heyward Right fielder, Outfielder

34
6 5
Dave Goltz is listed (or ranked) 34 on the list The Worst MLB Free Agent Signings of All Time
silentdasher added Dave Goltz Pitcher

35
17 26
Adrián Beltré is listed (or ranked) 35 on the list The Worst MLB Free Agent Signings of All Time
galenandrews added Adrián Beltré Third baseman - 5 years $64 million by Seattle Mariners

36
15 28
Derek Jeter is listed (or ranked) 36 on the list The Worst MLB Free Agent Signings of All Time
MikeCudak added Derek Jeter Shortstop

37
14 62
Miguel Cabrera is listed (or ranked) 37 on the list The Worst MLB Free Agent Signings of All Time
shockwavesam91 added Miguel Cabrera Designated hitter, First baseman, Third baseman - 8 years, $153 million, Detroit Tigers