Write a book, then query SI. They seem to be running an awful lot of book excerpts lately (Michael Lewis' piece on left tackles in the new issue, the Unitas piece a few weeks ago ...).
Seriously, I have nothing for you, but write a book.
I'd make a few copies and send it to several people, not just one. Look at the staff list and pick out five or six people...but not the whole staff.
What do you have to lose? It's not like Michael Silver is going to tell Deuce McAlister to run over you in his car. Worst case scenario is you never hear back. Best case? Well, sky's the limit, my man.
I think I read somewhere that Steve Rushin got his foot in the door with a submitted freelance story.
As an Amazon Associate we earn from qualifying purchases. Product prices and availability are accurate as of the date/time indicated and are subject to change.