91. Tim Raines
Typically, being the second best in your era results in enshrinement in the Hall of Fame. For Tim Raines, the second best leadoff hitter in his era, that has not been the case yet, although his time may be coming soon.
Perhaps part of why Raines was overlooked is because his career peaked at such an early age. From 1981, when Raines first became a regular, through 1987, Raines was one of the top players in the National League, making the All-Star game each season, leading the league in steals four times and runs twice while posting a .310/.396/.448 batting line with 504 steals and 719 runs. He appeared set to be one of the great leadoff men in history.
Then, injuries happened. While Raines was able to play until 2002, becoming one of the rare players to appear in four different decades, he just was not the same player. While he still had some flashes of his past speed, stealing 51 bases in 1991, he never again made an All-Star team or captured a stolen base title. His career numbers, a .294/.385/.425 batting line with 808 stolen bases, show the sudden decline he had during the middle to the latter part of his career.
These days, Raines may be remembered for two different moments. He was one of the players victimized by collusion in 1987, when after a dominant 1986 season, the only free agent offer he received involved a minimal raise from the Expos. Then, in 2001, Raines made history by being the second person to play in a game with his son, Tim Raines Jr., during a brief stint with the Baltimore Orioles.
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Tim Raines career was certainly solid enough, but he had the misfortune of playing in the same era with one of the greatest leadoff hitters of all time. One has to wonder how he would be remembered if he had either remained healthy or had played at a different time.