With me, I'd probably be chicken and pass both spins. Granted, there is the chance he could catch up, but I'll think of it this way:
If I hit a Whammy, the game's over, basically. I've only seen one person actually make up a $7,700 or more deficit with one more spin (see: Menard from 1984). Knowing this, even with the probabilities of hitting the Whammy, I'd still pass because:
If HE hits a Whammy, same deal. Not only that, but he'd have to make up $3,300, and, unless he hits some decent money or prize spaces (i.e. something at least $1,500), he probably won't catch up. Not only that, but he'd HAVE to do this twice, which means that, even if he caught you in one spin, he'd still have to fend off the Whammy again to pull off the victory.
The odds seem clearly in favor of passing here with the 2 spins, so that's what I would do.
Anthony