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Baseball The Worst MLB Free Agent Signings of All Time  

PhilWa
2.6k votes 271 voters 3.9k 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?

1
14 0
Pablo Sandoval is listed (or ranked) 1 on the list The Worst MLB Free Agent Signings of All Time
mal3607 added Pablo Sandoval First baseman, Third baseman

2
90 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
91 25
Josh Hamilton is listed (or ranked) 3 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

4
83 22
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
92 29
Mike Hampton is listed (or ranked) 5 on the list The Worst MLB Free Agent Signings of All Time
Mike Hampton Starting pitcher, Pitcher - 8 years, $121 million, Colorado Rockies

6
75 22
Jason Bay is listed (or ranked) 6 on the list The Worst MLB Free Agent Signings of All Time
Jason Bay Left fielder - 4 years, $66 million, New York Mets

7
86 30
Barry Zito is listed (or ranked) 7 on the list The Worst MLB Free Agent Signings of All Time
Barry Zito Starting pitcher, Pitcher - 7 years, $126 million, San Francisco Giants

8
69 20
B. J. Upton is listed (or ranked) 8 on the list The Worst MLB Free Agent Signings of All Time
B. J. Upton Center fielder - 4 years, $60 million, Atlanta Braves

9
72 26
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
111 52
Alex Rodriguez is listed (or ranked) 10 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.

11
57 20
Dan Uggla is listed (or ranked) 11 on the list The Worst MLB Free Agent Signings of All Time
Dan Uggla Second baseman - 5 years, $62 million, Atlanta Braves

12
49 18
Gary Matthews, Jr. is listed (or ranked) 12 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

13
69 33
Alfonso Soriano is listed (or ranked) 13 on the list The Worst MLB Free Agent Signings of All Time
Alfonso Soriano Left fielder, Second baseman - 8 years, $136 million, Chicago Cubs

14
47 22
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 Greatest Second Basemen of All Time

15
52 26
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
45 24
Albert Belle is listed (or ranked) 16 on the list The Worst MLB Free Agent Signings of All Time
Albert Belle Outfielder, Left fielder - 5 years, $65 million, Baltimore Orioles

17
73 48
Albert Pujols is listed (or ranked) 17 on the list The Worst MLB Free Agent Signings of All Time
Albert Pujols First baseman - 10 years, $240 million, Los Angeles Angels

18
48 30
Prince Fielder is listed (or ranked) 18 on the list The Worst MLB Free Agent Signings of All Time
Prince Fielder First baseman - 9 years, $214 million, Detroit Tigers

19
41 24
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 21
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
43 28
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

The Greatest Catchers of All Time

22
19 7
Shin-Soo Choo is listed (or ranked) 22 on the list The Worst MLB Free Agent Signings of All Time
DanielHanley added Shin-Soo Choo Right fielder, Outfielder, Center fielder

23
37 24
Adam Dunn is listed (or ranked) 23 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

24
41 28
Jonathan Papelbon is listed (or ranked) 24 on the list The Worst MLB Free Agent Signings of All Time
Jonathan Papelbon Pitcher - 4 years, $50 million, Philadelphia Phillies

25
14 5
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
41 35
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
53 50
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 21
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 Managers of All Time

29
12 9
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
33 31
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
33 31
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
7 5
Dave Goltz is listed (or ranked) 33 on the list The Worst MLB Free Agent Signings of All Time
silentdasher added Dave Goltz Pitcher

34
1 2
Carl Pavano is listed (or ranked) 34 on the list The Worst MLB Free Agent Signings of All Time
chaaad added Carl Pavano Starting pitcher, Pitcher - 4 year, $39.95 million, New York Yankees

35
18 28
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
16 31
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 64
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