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Baseball The Worst MLB Free Agent Signings of All Time  

PhilWa
2.8k votes 298 voters 4.1k 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
101 25
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
100 28
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
88 26
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
97 32
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
79 24
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
92 32
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
74 23
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
73 28
Mo Vaughn is listed (or ranked) 8 on the list The Worst MLB Free Agent Signings of All Time
First baseman - 6 years, $80 million, Anaheim Angels

9
22 2
Pablo Sandoval is listed (or ranked) 9 on the list The Worst MLB Free Agent Signings of All Time
mal3607 added First baseman, Third baseman

10
116 59
Alex Rodriguez is listed (or ranked) 10 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.

11
61 22
Dan Uggla is listed (or ranked) 11 on the list The Worst MLB Free Agent Signings of All Time
Second baseman - 5 years, $62 million, Atlanta Braves

12
52 20
Gary Matthews, Jr. is listed (or ranked) 12 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

13
61 28
Jacoby Ellsbury is listed (or ranked) 13 on the list The Worst MLB Free Agent Signings of All Time
Center fielder - 7 years, $153 million, New York Yankees

14
73 37
Alfonso Soriano is listed (or ranked) 14 on the list The Worst MLB Free Agent Signings of All Time
Left fielder, Second baseman - 8 years, $136 million, Chicago Cubs

15
52 24
Kevin Brown is listed (or ranked) 15 on the list The Worst MLB Free Agent Signings of All Time
Pitcher - 7 years, $105 million, Los Angeles Dodgers

16
80 52
Albert Pujols is listed (or ranked) 16 on the list The Worst MLB Free Agent Signings of All Time
First baseman - 10 years, $240 million, Los Angeles Angels

17
49 27
Albert Belle is listed (or ranked) 17 on the list The Worst MLB Free Agent Signings of All Time
Outfielder, Left fielder - 5 years, $65 million, Baltimore Orioles

18
45 27
Richie Sexson is listed (or ranked) 18 on the list The Worst MLB Free Agent Signings of All Time
First baseman - 4 years, $50 million, Seattle Mariners

19
52 34
Prince Fielder is listed (or ranked) 19 on the list The Worst MLB Free Agent Signings of All Time
First baseman - 9 years, $214 million, Detroit Tigers

20
45 30
Jonathan Papelbon is listed (or ranked) 20 on the list The Worst MLB Free Agent Signings of All Time
Pitcher - 4 years, $50 million, Philadelphia Phillies

21
18 6
Jason Schmidt is listed (or ranked) 21 on the list The Worst MLB Free Agent Signings of All Time
Statmeister added Starting pitcher, Pitcher

22
38 24
Juan Pierre is listed (or ranked) 22 on the list The Worst MLB Free Agent Signings of All Time
Outfielder, Left fielder - 5 years, $45 million, Los Angeles Dodgers

23
46 32
Johan Santana is listed (or ranked) 23 on the list The Worst MLB Free Agent Signings of All Time
Starting pitcher, Pitcher - 6 years, $137 million, New York Mets

24
41 28
Adam Dunn is listed (or ranked) 24 on the list The Worst MLB Free Agent Signings of All Time
Designated hitter, Outfielder, First baseman - 4 years, $56 million, Chicago White Sox

25
21 13
Shin-Soo Choo is listed (or ranked) 25 on the list The Worst MLB Free Agent Signings of All Time
DanielHanley added Right fielder, Outfielder, Center fielder