I started reading The Rise of the Vulcans by James Mann, a new (possibly not avail in bookstores yet) joint biography of the Bush foreign policy team: Rumsfeld, Cheney, Wolfowitz, Powell, Armitage, Rice. It looks like a terrific book, but I'm only about twenty pages into it. But here's a passage about Rumsfeld that has to get you thinking about what might have been:
For a generally conservative Republican congressman, Rumsfeld maintained some surprising friendships among the Democrats. One of his closest associates in the House of Representatives was Allard K. Lowenstein, a leader of the antiwar movement and perhaps the most liberal member of Congress at the time, who in 1967 led the fight within the Democratic Party to drop Lyndon Johnson as the party's presidential nominee. Rumsfeld and Lowenstein had served as congressional aides together in the late 1950s and once dreamed of buying a country newspaper together.
How different history would be if Rumsfeld had decided to wile away his days running a country newspaper with a rumpled, gay New York leftist!
(The Rumsfeld-Lowenstein friendship is confirmed in William H. Chafe's biography of Lowenstein, which is also one of the best books about the anti-communist left in the 50s and 60s, and the stress of Vietnam. According to Chafe, Lowenstein called on support from Rumsfeld, then a Nixon White House staffer, when faced with a tough fight for reelection in 1970. Rumsfeld obliged with very favorable comments to a local newspaper, but then was forced by Nixon to back off and formally endorse Lowenstein's opponent.)
[UPDATE: Yes (in response to a comment), I know that the issue of Lowenstein's sexuality is vastly more complicated than my characterization. He was an interesting, very complex person, which is another reason the Chafe biography -- sadly, out of print -- is worth reading.]