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Baseball The Worst MLB Free Agent Signings of All Time  

PhilWa
2.6k votes 278 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?
list ordered by

1
94 23
Carl Crawford is listed (or ranked) 1 on the list The Worst MLB Free Agent Signings of All Time
Left fielder - 7 years, $142 million, Boston Red Sox

2
93 25
Josh Hamilton is listed (or ranked) 2 on the list The Worst MLB Free Agent Signings of All Time
Outfielder, Left fielder, Center fielder - 5 years, $125 million, Los Angeles Angels

3
84 22
Bobby Bonilla is listed (or ranked) 3 on the list The Worst MLB Free Agent Signings of All Time
Right fielder, Outfielder, Third baseman - Still owed $30 million by the Mets through 2035

4
93 29
Mike Hampton is listed (or ranked) 4 on the list The Worst MLB Free Agent Signings of All Time
Starting pitcher, Pitcher - 8 years, $121 million, Colorado Rockies

5
76 22
Jason Bay is listed (or ranked) 5 on the list The Worst MLB Free Agent Signings of All Time
Left fielder - 4 years, $66 million, New York Mets

6
88 30
Barry Zito is listed (or ranked) 6 on the list The Worst MLB Free Agent Signings of All Time
Starting pitcher, Pitcher - 7 years, $126 million, San Francisco Giants

7
70 20
B. J. Upton is listed (or ranked) 7 on the list The Worst MLB Free Agent Signings of All Time
Center fielder - 4 years, $60 million, Atlanta Braves

8
114 52
Alex Rodriguez is listed (or ranked) 8 on the list The Worst MLB Free Agent Signings of All Time
Shortstop, Third baseman - 10 years, $250 million, Texas Rangers and 10 years $275 million with the New York Yankees.

9
72 26
Mo Vaughn is listed (or ranked) 9 on the list The Worst MLB Free Agent Signings of All Time
First baseman - 6 years, $80 million, Anaheim Angels

10
57 20
Dan Uggla is listed (or ranked) 10 on the list The Worst MLB Free Agent Signings of All Time
Second baseman - 5 years, $62 million, Atlanta Braves

11
15 1
Pablo Sandoval is listed (or ranked) 11 on the list The Worst MLB Free Agent Signings of All Time
mal3607 added First baseman, Third baseman

12
70 33
Alfonso Soriano is listed (or ranked) 12 on the list The Worst MLB Free Agent Signings of All Time
Left fielder, Second baseman - 8 years, $136 million, Chicago Cubs

13
49 18
Gary Matthews, Jr. is listed (or ranked) 13 on the list The Worst MLB Free Agent Signings of All Time
nathaniel.freiberg added Outfielder, Center fielder - 5 years, $50 million, Los Angeles Angels of Anaheim

14
48 22
Kevin Brown is listed (or ranked) 14 on the list The Worst MLB Free Agent Signings of All Time
Pitcher - 7 years, $105 million, Los Angeles Dodgers

15
53 26
Jacoby Ellsbury is listed (or ranked) 15 on the list The Worst MLB Free Agent Signings of All Time
Center fielder - 7 years, $153 million, New York Yankees

16
46 24
Albert Belle is listed (or ranked) 16 on the list The Worst MLB Free Agent Signings of All Time
Outfielder, Left fielder - 5 years, $65 million, Baltimore Orioles

17
75 49
Albert Pujols is listed (or ranked) 17 on the list The Worst MLB Free Agent Signings of All Time
First baseman - 10 years, $240 million, Los Angeles Angels

18
49 30
Prince Fielder is listed (or ranked) 18 on the list The Worst MLB Free Agent Signings of All Time
First baseman - 9 years, $214 million, Detroit Tigers

19
42 25
Richie Sexson is listed (or ranked) 19 on the list The Worst MLB Free Agent Signings of All Time
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
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
Starting pitcher, Pitcher - 6 years, $137 million, New York Mets

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 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
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
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 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
First baseman - 8 years, $180 million, New York Yankees

27
54 50
Robinson Canó is listed (or ranked) 27 on the list The Worst MLB Free Agent Signings of All Time
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 Right fielder, Center fielder - 8 years $160 Million by LA Dodgers.

29
12 9
Darryl Strawberry is listed (or ranked) 29 on the list The Worst MLB Free Agent Signings of All Time
silentdasher added 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
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
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 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 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 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 Shortstop

37
14 65
Miguel Cabrera is listed (or ranked) 37 on the list The Worst MLB Free Agent Signings of All Time
shockwavesam91 added Designated hitter, First baseman, Third baseman - 8 years, $153 million, Detroit Tigers