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Most worried i've ever been about getting robbed was with my camera gear.
I was getting a train to Paris from London - decided to take a long gloomy underpass near Buckingham Palace at 4am.
Didn't realise it literally had about 100 homeless men sleeping along the walkways inside.
About half of them staring at me.
I had about £2000 (~$3000 at the time) worth of equipment hanging off my shoulder and back in very obvious camera bags.
I was also dragging a luggage bag behind me which made a loud CLACK CLACK CLACK as it hit every. single. fucking. paving slab.
I had images in my head of having to swing on some boney homeless guys with my titanium tripod and dent some brains.
Fortunately no one stood up.
Anticlimactic - but its the only time I did kinda wish I had a MAC10 in my pocket.