This song is about a slick gambler who always seems a step ahead. At first, Seger seems to be talking this guy up, enamored with his winning ways and how he's still the same. But at the end of the song, we learn this isn't the case: Seger turns and walks away from him because he hasn't changed, and there's nothing left to say. It's like reconnecting with an old friend, only to be reminded of why you stayed apart.
Seger says it's not about a specific person, but a composite of "Type A, overachieving" people he's encountered, particularly in Hollywood, where he lived for a few months while recording the Stranger In Town album. There aren't as many of these types in Michigan, where Seger is from.