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baseball The Worst MLB Free Agent Signings of All Time  

PhilWa
2.3k votes 225 voters 3.6k views Embed

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
77 21
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

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2
75 21
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
81 27
Mike Hampton is listed (or ranked) 3 on the list The Worst MLB Free Agent Signings of All Time
Mike Hampton Starting pitcher, Pitcher - 8 years, $121 million, Colorado Rockies

4
67 19
Bobby Bonilla is listed (or ranked) 4 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

5
68 20
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
78 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
62 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
100 46
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
67 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
52 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
47 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
63 28
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
44 21
Kevin Brown is listed (or ranked) 13 on the list The Worst MLB Free Agent Signings of All Time
Kevin Brown Pitcher - 7 years, $105 million, Los Angeles Dodgers

14
42 22
Albert Belle is listed (or ranked) 14 on the list The Worst MLB Free Agent Signings of All Time
Albert Belle Outfielder, Left fielder - 5 years, $65 million, Baltimore Orioles

15
40 22
Richie Sexson is listed (or ranked) 15 on the list The Worst MLB Free Agent Signings of All Time
Richie Sexson First baseman - 4 years, $50 million, Seattle Mariners

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16
62 41
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
42 24
Jacoby Ellsbury is listed (or ranked) 17 on the list The Worst MLB Free Agent Signings of All Time
Jacoby Ellsbury Center fielder - 7 years, $153 million, New York Yankees

18
36 20
Juan Pierre is listed (or ranked) 18 on the list The Worst MLB Free Agent Signings of All Time
Juan Pierre Outfielder, Left fielder - 5 years, $45 million, Los Angeles Dodgers

19
40 25
Prince Fielder is listed (or ranked) 19 on the list The Worst MLB Free Agent Signings of All Time
Prince Fielder First baseman - 9 years, $214 million, Detroit Tigers

20
16 4
Shin-Soo Choo is listed (or ranked) 20 on the list The Worst MLB Free Agent Signings of All Time
DanielHanley added Shin-Soo Choo Right fielder, Outfielder, Center fielder

21
40 26
Johan Santana is listed (or ranked) 21 on the list The Worst MLB Free Agent Signings of All Time
Johan Santana Starting pitcher, Pitcher - 6 years, $137 million, New York Mets

22
12 2
Jason Schmidt is listed (or ranked) 22 on the list The Worst MLB Free Agent Signings of All Time
Statmeister added Jason Schmidt Starting pitcher, Pitcher

23
38 26
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
32 22
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
37 31
Mark Teixeira is listed (or ranked) 25 on the list The Worst MLB Free Agent Signings of All Time
Mark Teixeira First baseman - 8 years, $180 million, New York Yankees

26
48 45
Robinson Canó is listed (or ranked) 26 on the list The Worst MLB Free Agent Signings of All Time
Robinson Canó Second baseman - 10 years, $240 million, Seattle Mariners

27
3 0
Jason Heyward is listed (or ranked) 27 on the list The Worst MLB Free Agent Signings of All Time
TRENT13 added Jason Heyward Right fielder, Outfielder

28
9 7
Darryl Strawberry is listed (or ranked) 28 on the list The Worst MLB Free Agent Signings of All Time
silentdasher added Darryl Strawberry Right fielder, Outfielder

29
20 19
Matt Kemp is listed (or ranked) 29 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.

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30
30 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
29 29
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
5 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
0 0
Pablo Sandoval is listed (or ranked) 33 on the list The Worst MLB Free Agent Signings of All Time
mal3607 added Pablo Sandoval First baseman, Third baseman

34
4 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
15 23
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
11 23
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
11 55
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