What's The Largest Amount Of Cash You Have Ever Handled?

Bobby , I think if you had angled that gold bar just right you could have pulled it out of that box .
But then you would have been tackled by a bunch of dealers with guns drawn.

Over a million in 1966. As a kid, I was given this opportunity by an older friend. Since then, about $14.

Actual cash: only a few thousand dollars.

I don't do large Cash transactions But I have filled a bag pretty much full of Gold that I had to pry loose from the discharge end of a ball mill I was relining once.
Probably about 20kg of gold all up, The Mine manager was pretty stoked when I handed it to him

After I graduated from High School I worked for a time as a bank messenger for a really large bank that sat across the street from the Chicago FRB.

One day, back in the mid-60's, shortly before lunch the bond department sent a request up for a messenger. I drew the assignment and went down to the department, got a brief case which they filled and sent me on my way to another major downtown bank about 6 blocks away. Since I was hungry I stopped off for lunch. In all it took me about 30 minutes to get to the bank. Unknown to me I didn't know that when I was at the other bank in 10 minutes they called the bank that I worked for which sent out armed guards looking for me. It turns out that what I was carrying at the time required a bonded messenger along with two armed guards. I was carrying $10 million in negotiable bearer bonds. To say that they were not happy with was an understatement. The normal practice was to ask the messenger is he was bonded. They didn't and I wasn't. That whole adventure didn't phase me because I really didn't know what was in that brief case. Needless to say I wasn't tempted. That's not to say that today I wouldn't be wondering...........

Added to that I had a high school buddy who worked in the cash vault at another bank, and about once a week I'd go over there for lunch and together with a couple other guys were would play poker in the vault for some magnificient amounts that we've never duplicated again. When the management found out what we were doing I was never allowed anywhere near the cash vault again.

Since that time I have never held in my hands anywhere near those figures again.

In the following years, nothing ever approached what that might have been.

I used to do the casino count on a large cruise ship after a 7 day run. Given much of the money was in small denominations from bill feeds on slot machines that was a lot of physical cash.

Largest amount was probably the count from a Mayfair casino... one nights take was £15million. About half of that was mainly in £50 notes...the other half in plaques (representing money already exchanged at the cash desk)

One night I dealt a game of roulette to a guy who was betting £200,000 per spin and burnt through more than £8million barely winning a single wager.

Money is all relative...and I wasn't earning a huge wage to perform these duties but it plays with your sense of value to be constantly be exposed to such things.

Well, there was that one time in 2003 (I have reasons to suspect it was the 20th of March) when I counted the cash register at a small shop near my school. Can't actually remember how much money it was... probably only a few thousand rubles (so like $200) - the shop was tiny; but that was the only time I actually counted a shop cash register.

Other than that, my grandmother's "rainy day fund" (or whatever it actually is - I've been told once that it's actually mostly intended for her eventual funeral). A thick stack of 5000 ruble notes. I think there's about $1000 in there (by the pre-2014 exchange rates, at least - more like $600 today).
Every so often, when we really were running out of available money at home and other members of the family were too busy, I went and asked grandma to give me one of these 5000 ruble notes. She explained where she put the bag this time, had me bring it to her, and carefully took out a 5000. I was always surprised (though I tried not to show it too directly) that she had that much money.

On the "up a creek if you lose it" part... one time in the early 2000s (or maybe late 1990s), I was going with my mother to a glasses shop to buy a pair of glasses, with 1700 rubles in large bills in my pocket. I'm not sure what happened, exactly, but at some point I realized the money wasn't in my pocket anymore. So I looked back... the bills were lying on the asphalt about 20 meters behine me
I did pick them up successfully (and we did buy the glasses - can't recall which particular ones they were, sadly, so no idea what happened to them), but I was really worried about losing so much money.