I think a better question is “did he apply?” My bet is that letter was sent well after he got his early acceptance to Stanford. Although either way, I do think MIT would have found that letter hilarious and it would have worked in his flavor rather than against him in reviewing his app. I happen to like the John Mongans of this world.
As noted above this is a VERY old letter. I think Michael Benhke left MIT in 1997.