“Insurance is exactly the opposite of a lottery” was posted on the newsgroup sci.math on June 14, 1999. Both require paying smalls sums, but with insurance, you win the big payoff if you lose (die early).
 
“Buying insurance is almost the exact opposite of buying a lottery ticket” was posted on Reddit—Shower Thoughts on April 24, 2014. “Buying insurance is the opposite of buying the lottery” was posted on Reddit—Shower Thoughts on July 1, 2016.
 
   
Google Groups: sci.math
Insurance = Lottery—> Don’t Buy Insurance!   
Bennett Standeven
6/14/99
The difference between the two is that with a lottery, you want to win,but with insurance, you want to lose.
 
David Kastrup
6/14/99
(...)
Yes, because an insurance is exactly the opposite of a lottery.  In a lottery, you pay small amounts so that there is a small chance of you getting a large return.  In an insurance, you pay small amounts so as to avoid having a small chance of having to *pay* a large amount that will break your neck.
 
Twitter
Miriam BrowningNance
@miriambn
I keep getting letters from insurance that say “This is not a bill, but you MAY owe $X.” It’s like the opposite of a lottery ticket.
9:05 PM - 7 Sep 2011
 
Reddit—Shower Thoughts
Buying insurance is almost the exact opposite of buying a lottery ticket
submitted April 24, 2014 by Windshield_Wiper
COMMENTS
Han-ChewieSexyFanfic
Heh, I had this thought recently. I think it went “Buying insurance is buying a lottery ticket you really hope you don’t win”.
     
Reddit—Shower Thoughts
Buying insurance is the opposite of buying the lottery.
submitted July 1, 2016 by Patiiii
 
Twitter
sleuth
@metacarpi
you ever think about how insurance is like the opposite of a lottery
8:34 PM - 23 Dec 2017
 
Reddit—Shower Thoughts
Paying for insurance is the exact opposite of buying a lottery ticket
submitted May 11, 2018 by beyond_netero
Spending money each week while hoping an extremely unlikely event won’t occur vs. Spending money each week while hoping that an extremely unlikely event will occur.