Lyric discussion by danltd 

The album "Sailing to Philadelphia" was released in 2000, so a song about the 2001 season was fiction. The song is actually based on the 1994 CART racing season. The circuit changed the sequence of races every year and the only year that went from Phoenix to Monterrey in the order described in the song was 1994. CART did the Indy 500 until 1996. There were no reported serious injuries in the 9 crashes during 1994 Indy race, but in 1995 Stan Fox was critically injured. Knopfler got much of his background information from Swedish racer Stefan Johansson who ran the CART circuit from 1992 until it folded in 2003. Johansson had a successful CART racing career even though he never won a race. I agree the song has allegorical implications, as do many other Knopfler songs.

I suggested in a comment below that this song might've been inspired by Kenny Bräck, but in this interview Kenny himself says that SaN was indeed inspired by Stefan "Lill-Lövis" Johansson:

An error occured.