I don’t know about other bike messengers, but I seemed to attract office workers who wanted to race me at the end of the day. Usually, they rode expensive road bikes, were decked out in spandex outfits, and wore clip-in shoes. I road a mountain bike with road slicks, and wore tennis shoes, shorts,and company shirt. There was for a long time one guy in particular who pass me around city hall as I rode up McAllister. We would play leap frog up until we hit Webster.
At no point was I ever an active participant, but this guy would always check me after passing. I just rode at a steady even pace, my only goal to get home without incident after a 10 hour day in the saddle. He wasn’t a very good rider. McAllister kind of rolls up and down until it hits the hill from Webster up to Divisadero. The thing that I noticed was that anytime we were going up I passed him, going down he passed me. My pace never changed.
On this day, I hit Webster well ahead of my racer; the light was red. I decided to have a smoke. The light was green as I put away my lighter. Racer guy passed me, getting up out of the saddle as he climbed from Webster to Fillmore (I should put climbed in quotes here as it’s a mild grade). He looked back. I started rolling, sitting in my saddle, beginning the climb to Divisadero. I was about two-thirds of distance from Webster to Fillmore as he began to really climb, after Fillmore there is an actual steep incline. He was standing and cranking. He was not a good climber, neither was I. I caught up to and passed him, seated and smoking about half way between Steiner and Pierce. As I passed him, I pulled the cigarette from my lips, blew some smoke out, and greeted him, “How’s it going?”.
Around Scott where McAllister peaks, I looked back to see him as he turned on to Pierce; he was sitting. I never saw him again.