Very tough question which probably is impossible to answer. And we shouldn't really even try.
The very first fraternity was Phi Beta Kappa -- which, of course, is now the academic honorary. But they're not a social fraternity at all anymore. But they're the oldest, so do they have the "most" history?
Many fraternities (and I include in that number sororities -- which consider themselves fraternities) are rich in history and tradition, dating back to the 1700's and 1800's. Many are much younger. So, how do you measure?
Many Greek Letter Organizations (some people would say most -- I'm not sure of that) have their roots in the Masonic movement. Or at least many of the early founders of many fraternities were Masons. So maybe many of our Rituals are similar. I've read that that's true.
If all goes well, we will never know who has the most secrets. Because secrets are just that -- secret!
And what difference does it really make? It's not a contest. My Ritual and my fraternal oath are important to me -- but unless you are a Delt, they mean nothing to you -- except for the way the values involved affect how I relate to you and other human beings.
Fraternally,
DeltAlum
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