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Henman is a decent pick but I'd say Davydenko.

Made 4 slam semifinals across 2 different events (and 3 of those 4 SF losses came against Federer during his golden years), and a further 4 quarterfinals, won 3 masters 1000 titles and an ATP Finals title, has titles on most kinds of conditions (indoor hard, outdoor hard, clay and carpet), has a winning H2H vs Nadal and has wins in slams over the likes of Nalbandian and Murray who of course both made slam finals themselves.
 

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Neither consistent nor for a long span, but at the top of his abilities, James Blake would also have all the tools to be a slam finalist.

Saying he's the greatest non-finalist would probably be too much but you don't want to read only the obvious.
 

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Dibbs is the best. 20+ titles and 2 GS SFs. As for the last 20 years, surprised to see no mentions of Haas.
 

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Dimitrov is still young and still has time to reach a slam final and maybe even win a couple, but he's my pick at the moment.


He's won a Masters1000, the WTF, he's reached 2 slam semi finals, he's been the no.3 player in the world and a consistent top 10 player yet he's still never reached a slam final.
 

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Dimitrov is still young and still has time to reach a slam final and maybe even win a couple, but he's my pick at the moment.


He's won a Masters1000, the WTF, he's reached 2 slam semi finals, he's been the no.3 player in the world and a consistent top 10 player yet he's still never reached a slam final.
Davydenko has 3 Master 1000 titles, the WTF, more SFs at slams, and over DOUBLE the # of titles

obviously he is a much stronger contender in this respect than Dimitrov. Grigor has time left in his career to change that though obviously, (assuming he doesn't make a slam final at any point)

Davydenko's slam numbers blow Dimitrov's out of the water too (Davydenko: 4 SFs, 6 QFs) (Dimitrov: 2 SFs, 2 QFs)
 
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