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I'm going to say Mr. HighIncome started off like most of us, making $20,000 a year, and added $20,000 to that every decade thereafter. (I think most people didn't start off in their 20's making $100,000 a year, although I'm sure a few did.) [This looks to me like someone who climbs the middle-management ladder.]

I'm in that group, and I have never had a manager title - and hope I never do, until my brain slows down too much to stay in a technical line of work ;).

I think you somewhat miss the point by looking only at average life expectancies and incomes. Some low income people will live long lifes and collect benefits for a long time, and some high income people will have short lives and never collect a cent. There is a lot of redistribution going on.

Also, aren't you undercounting the SS taxes by half ? There is both an employee and employer paid part.
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