What he achieved by saying, "Even if I lose, I win," is obvious whether it was the truth or a lie. Elan believed (as do the people on the forum who take what Tarquin said as gospel truth) that there was no way he could truly defeat Tarquin, even if the entire Order was able to kill him.
If Tarquin had said, "If your adventuring group kills me...well, yeah, then I'll be sad about having lost," Elan's path would have been clear and the forum would have had many fewer people arguing that Tarquin had already won.