In my opinion, this is a pretty funny situation. I love his podcasts with Cousin Sal on sports betting and picking NFL lines. I also love reading his Vegas Diaries. It is not surprising (the most surprising part is that they did not realize this before hand).
On another note, I think the blog post had one particularly interesting passage on the funny conundrum of the position Simmons has established:
"What interests me about this story is the continuing evolution of Bill Simmons. In a nutshell, the great secret to the incredible success of Bill Simmons is his ability to simultaneously be mainstream and counter-culture. He is a journalist (griping about press credentials for his Grantland writers) and he's not a journalist (those Vegas gambling trip columns). He is able to tape podcasts with his buddies... and President Barack Obama. He can write about basically anything he wants under the umbrella of the biggest sports network in the world. It is the appeal and paradox to Simmons, and now the appeal and paradox to Grantland."
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