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Impossible to say, because you can’t objectively compare players from different era’s and also because the concept of “greatest” is not strictly defined. Is the greatest the one who won most titles in a career? Or the one who was most dominating at the top of her game? The first option favours players with long careers such as Serena Williams and Martina Navratilova. On the other hand, those who played for a shorter time can’t just be estimated by multiplying their results in a shorter career by two or three, as nothing guarantees they would have kept competitive over a longer time span. Another question is how you should consider titles in double. Some great players have a plethora of those, like Navratilova, other rarely if ever played doubles. Yet another consideration is how strong the competition was at the time of those results.
Macho man the cream of the crop shirtFor example, Evert and Navratilova both won 18 grand slam titles, but being born just two years apart and having faced each other 14 times in grand slam finals and 8 times in grand slam semifinals they obviously took away several titles from each other. Compare this with how Graf won 11 of her 22 GS titles after a crazied fan of hers stabbed Seles, who at the time was constantly beating Graf (except on grass), and think how many titles Navratilova would have had if Evert was removed (or vice versa). Or consider that Serena Williams was born in 1981 and would have had formidable competition not only in Venus (1980) but also in Hingis (1980), Henin (1982) and Clijsters (1983). Now all three of those had their careers shortend, either by injuries or personal choices. I think it’s safe to say Serena would have had a much harder time getting to 23 GS titles otherwise.