I think I have maybe figured out your hint. The picture is Jack Kerouac, and the only thing I can figure by your " obscure hint" is you are adding fantasy baseball. If anybody else has a guess please chime in. Here is what leads me to beleive this, 
 
Jack Kerouac's fantasy baseball league 
Unbeknownst to his close friends, Jack Kerouac invented a fantasy baseball game and played it for most of his life. 
 
[Kerouac's game charted] the exploits of made-up players like Wino Love, Warby Pepper, Heinie Twiett, Phegus Cody and Zagg Parker, who toiled on imaginary teams named either for cars (the Pittsburgh Plymouths and New York Chevvies, for example) or for colors (the Boston Grays and Cincinnati Blacks). 
 
He collected their stats, analyzed their performances and, as a teenager, when he played most ardently, wrote about them in homemade newsletters and broadsides. He even covered financial news and imaginary contract disputes. During those same teenage years, he also ran a fantasy horse-racing circuit, complete with illustrated tout sheets and racing reports. He created imaginary owners, imaginary jockeys, imaginary track conditions.

Our weeks or yours?

This guy sounds just like me.... Are you making me a mod?

Reading through this and the history of flea, and what it meant to Ori. I think he's going to wow us. The transfer to AOL and his comment that he took it as far as he could. He has had a year and a half to bring his baby to the net.