I wouldn't fade daringly, he's a knowledgable gambler. He posts here and other boards. He had an awesome run in Arena football a few years back at another site. I believe Pinnacle even hired him as a consultant for AFL. He's not a kid, he's an attorney.
He may lose his bet with Steve Fezzik, but don't expect him to continue to lose at this rate. I'd expect him to regress to the mean and edge closer to break-even.
This is not an idiot making these picks, more like a guy on a bad run.