LordHawk/Openeye
I have never had the pleasure of speaking to either of these players, but OpenEye's forum presence and guides are well-known and well-respected. I also don't really like LordHawk's style of leading. I feel that the only people who will choose LH are the people who know him very well.
IFeelYou/PZA7
Again, I have never really met either player. It's of course always nice to have a player who can perform as well in the rankings as IFY, but PZA7 hasn't exactly slacked there either. Both are in leadership positions in LEGION, if I'm not mistaken, and as I have heard nothing bad about either in terms of their leadership, I cannot speak to that aspect of their playing. I'll have to leave this one up to players that know these two better.
RulerofMiddleEarth/Meganluvsme
I don't honestly think that, purely based on reputation, this is a difficult choice at all. Both were leaders of large clans early on (Watch and E=MC2), and both seem to have lead their tribe well enough for them both to have survived until this point. Although I haven't spoken to either player, Meganluvsme was often flamed in the forum earlier on in the world for making poor leadership choices. Add that to the fact that RoME was often near the top of the standings early on in the world, and for me at least, that comes to better play and leadership on the part of RoME.
Pinder/2hot
Honestly, I have quite a bit of respect for this guy. For the amount of flaming he has received on this forum, he has managed to remain quite calm and composed. A few PR slip-ups, like when he was flame-baited by 1921, but all in all a fairly solid representation of himself. Although he seems to like nobling barbs and internalling other players, he has done fine up until this point, and there's no reason to believe he won't continue to do so. Honestly, if you're going to criticize someone to the extent he has been criticized, you can at least back it up by attacking him (DitM :icon_redface
. Uhm, that's all been about Pinder. I'm not even going to touch the other guy, he's not worth mentioning.
So there you have it: I would take OpenEye, 1/2 each of IFeelYou and PZA7, RulerofMiddleEarth, and Pinder.