There are different venues for pvp.

World PvP is one thing.
Battleground pvp is another.
And Arena pvp is yet another beast.

I would have to say, being the best at one aspect of pvp would not necessarily even give an edge at another aspect.

The ability to control 36 toons at once is quite impressive.
In the world pvp environment, I don't see too many standing up to that.
However, given equal numbers on each side I don't know who is best at world pvp.
Although equal numbers makes a test more even, we also have to realize war is rarely fair.

How well geared are your top 5 toons?
Arena is one measurement of pvp skill as well.
Although getting to 1850 with a mixed composition, say 2 melee, 2 ranged and 1 healer (all played by the one person) of five different classes is probably much more skilled then 2000 with one class.
Or maybe skill isn't the right word there, maybe its better at macro's and planning to coordinate.

I would tend to say... highest 5-man arena gets one award.
Highest BG rating, when that comes out is another rating.
World PvP is a third category, but its much harder to compare teams/players there, as its subjective.