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Notes -
Funnily enough it was the night of the 2020 US election and the trade was over the number of senate seats that the Democrats won on the night. He was your typical snooty nosed liberal who I think wanted to impress a girl also present by claiming to be "leftier than thou" with all of us. At the very least his actions pissed me off pretty early in the night. Also he was the type of "all bluster, no substance" person that is unfortunately pretty common at Oxbridge (wanted to go into politics after graduation etc.) He loudly proclaimed that everyone hates Republicans and was making unprompted statements like "there is a 50% chance Dems get at least 52 seats tonight" and I decided to teach him a lesson. All I did was check 538 predictions for what the real probability of that was and challenged him to trade, mentioning that if he really thought there was a 50% chance Dems got 52 seats he should be very happy to do a 4:1 trade with me that it's not going to happen (maybe he said 53, I can't exactly remember as it was 2 years ago and I very frequently do these sorts of trades with coworkers).
I suspect because there was a girl he wanted to impress and he didn't want to look like a pussy he didn't back down, most people I propose trades to back down when you suggest involving real money and at that point I decided it would be good to teach him an expensive lesson. I first proposed to do the trade for a small amount, my £80 vs his £20 but he taunted me (or at least I took it as a taunt) by saying I don't really believe in my position considering what a small proportion of my income £80 is given my job salary. At this is was pretty damn pissed off, and decided to properly teach him a lesson and asked him if he wanted to raise the bet size to my £2,000 vs his £500 and he accepted (it's a bit like redoubling in Bridge after your opponents double, they say they can beat you and you say "no you can't we're gonna punish you for thinking you can beat us"). We both transferred the money to the bank account of a trusted mutual acquaintance and waited until morning, whereupon I got my £2,500 once it because clear that it wasn't possible for Dems to get 52 seats any more and the best part was that he didn't even flip out or anything at me, despite having lost significant money and his body language showing he very clearly wanted to do so, because the girl was still there and it would look like he was having a tantrum.
To this day I haven't talked to him again, I saw him a few times walking around college after that event but never exchanged words, he should have graduated by now.
Looking back this probably wasn't the best bet to make because of the Georgia runoff which could have locked my (and his) money up for a pretty long time, but hey it worked out for me in the end.
You both sound like highly unpleasant people but then again, a fool and his money are soon parted, so you did teach him a valuable lesson.
Funnily enough pretty much nobody who actually knows me in person decently well would describe me as unpleasant. People generally consider me to be fun, easy going, patient and extremely generous. Perhaps I'm giving off the wrong vibes with my writing style, I don't know...
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