On a recent Wednesday evening, ESPN commentator Skip Bayless sat in a booth in the bar at the Midtown Hilton nursing a Diet Coke and quietly watching two basketball games.

Yes, quietly.

“By nature, I am quiet off the air,” he said. “My mom was real loud and that made me speak only when spoken to. But even as a child, if you challenged me, you would get both barrels.”

Mr. Bayless, 60, wore a navy-blue sweatshirt, matching cargo sweatpants and white-and-navy Fila sneakers. “You haven’t challenged me,” he pointed out. “I’ve agreed with your opinions.”

Mr. Bayless and The Observer found a surprising amount of common ground during our interview: The Atlanta Hawks are perennially overrated; the 2002-03 San Antonio Spurs were the best team in the history of that franchise; and LeBron James doesn’t deserve the MVP award because his team is too good.

Agreeing with Mr. Bayless is a disorienting experience. Read More