Perhaps I can shed some light on the Wellington issue for those unfamiliar, basically as you can imagine it started by drunken capers, but any time Glasgow City Council removed the cone a new one would appear. Eventually (so the story goes!) it became a futile task to remove the cone the council deemed it to be a health and safety issue since if a cone was up there already nobody would climb the statue to put a new one on, so they left it. (This may not be entirely true, the council claim it costs them £10,000 a year to remove the cones, yet I never see it happen). There has been a cone on his head for the best part of three decades. It has become a symbol of Glasgow and our sense of humour, even appearing on tourist guides and other areas of popular culture. It's worth noting that the statue is right outside the Gallery of Modern Art.
I'd like to think the man himself wouldn't be too bothered about it, his statue is now an endearing part of Glasgow culture. Everyone knows where he stands, yet most could not tell you any of the nearby statues by name. Last year the council drew up plans to raise the plinth to double it's height, and this started mass petitions and protest by the people of Glasgow.
During the games the council replaced the cone with a golden one. The statue was also referenced several times in the opening ceremony.
So basically, Wellington and his traffic cone hat are one of the most iconic symbols of Glasgow, and this is why the cone appears on the medal.