To clarify the chronology and background here: Rota was born in 1932, and starting teaching at MIT in 1959. He died in 1999.
Rota was not a boomer; he taught the boomers (and the succeeding generation). The students he is talking about here are the young boomers-to-be. This page is dated 1997 but it reads like a reprint of something written much earlier. I was an undergraduate at Caltech in 1968-72 and this sounds similar to the faculty, students, and workload there at that time.
Regarding WW2, Rota was a child in Italy during the war until his family fled in 1945 to escape the fascists. He reached the US in 1950 via Switzerland and Ecuador [1]. Not really a pampered boomer upbringing.