My son, a 210 lb. body-building nut who likes to spend 99% of his time in the big ring and smallest cog, complained about being unable to shift back to big after the occasional, brief stint in the small ring. I had to explain that there must be a reduction in chain tension, or the chain can't possible climb onto a bigger circle. "Oh, I get it!" he said. He's doing better now.

An analogy is standard shift in a car: You must let up a little on the gas when shifting, or you will inevitably damage the clutch and/or the trans.

The best way to deal with Bill is to sabotage his bike before the race.