The pint mug is intriguing. Replicas were definitely awarded as early as 1923. I think this will have a been a "whip round" by his mates to commemorate Jimmy's win after years of trying. Originally gold medals were awarded, and I can't think what year silver and bronze reps were first awarded. I remember seeing the replica that Chris Stead won in 1923,(used to stay at Steads Hotel in Onchan in the 60's) so I think they began after WW1. Larry will know.
Incidentally Jimmy Simpson was a big pal of my father (Allan Jefferies, grandfather of DJ), I would love to be able to ask both of them thousands of questions regarding the old days. Just amazing that JHS was the first man to lap at 60,70 and 80mph. I remember my father saying that when Jimmy first lapped at 60, the ACU were under pressure to ban the TT, and that's when they looked at running it in Belgium.