Demandred is posing as ... Olver
by Shishka
When Mat began exhibiting his extraordinary abilities as a general in FoH, Demandred took notice. He could not tolerate yet another rival for "greatest living general", and decided to take steps to rectify the situation.
The Plan: Disguise himself as a 10yr old waif, insinuate himself into Mat's coterie, and sabotage Mat's plans from within.
By the end of LoC, Demandred had achieved the first part of his plan with a brilliance and aplomb that defies description (at least in his own mind). Not only had he become a member of Mat's company, but Mat had taken a liking to him and employed him as his own personal messanger. He even got the chance to kill one of al'Thor's women, but was unfortunately foiled in the attempt. Nevertheless, Demandred was ecstatic - the plan had taken shape better than even he could have hoped. The only problem - no matter what he tried, he could not make his MoM disguise both suitably puny AND handsome. And since he realized no one would believe a 10yr old could be 6'3", he sacrificed his incredible good looks for the sake of plausibility. The sacrifice chafed, but he tolerated it for the greater good.
Unfortunately, since ACoS the scheme has been less than successful. As it turned out, Mat was not interested in the military opinions of a 10yr old (go figure), so Demandred's plan to undermine Mat's strategies has been a complete and utter failure. His only 3 solaces are: 1) he gets to ride horses from time to time, and 2) he gets to play Snakes and Foxes whenever he wants. He'd always found the game challenging in the AoL, so the chance to hone his mind during his "down time" was a welcome opportunity.
As for the 3rd solace ... it's best explained by the following RJ quote, from an ACoS booksigning in Trenton, NJ, in July '96:
Q: The Guide mentions that Demandred was a well respected general during the War of Power, who switched sides due to his jealousy/contempt for LTT. Can you tell us anything else about him?
RJ: Well, a little known fact about Demandred is that he always enjoyed resting his head on the bosom of well-endowed women. It was a favorite pastime of his, and one of his few traits that his male contemporaries were actually quite jealous of.