I think I found this link at Dailykenn.com, but in any case, it's a fascinating question, asked over at National Review Online. Go there and give it a read, and then I'll give my reaction.....
If Reagan Had Picked Rumsfeld as His Vice President, Would We Never Have Had President Clinton?
My reaction is maybe. Clearly, Rumsfeld would have been a good choice for Reagan. His resume wasn't as good as Bush's, but his credentials were solid. I doubt that he would have ever been perceived as wishy-washy as Bush was, and I'm virtually certain he would not have picked Dan Quayle as his VP. My guess it that it would have been either Jack Kemp or Howard Baker. Let's say Baker to add a Southerner to the ticket. He would certainly have won over Dukakis, for the same reasons that Bush did.
And, assuming that Gulf War I would have happened as it did, and the Soviet collapse had done so as well, I expect Rumsfeld would have been much better at taking credit for both, and would not have been challenged for the nomination by Pat Buchanan, changing the 1992 from a downer to an upper for Rumsfeld. Likewise, a Perot candidacy very well might not have taken place. Now, with Baker on the Repubican ticket, Clinton would most likely not have picked Gore as his running mate, and would have gone with, say Jerry Brown, and regretted it. My guess is that the election would have been closer than in our history, but that Rumsfeld would have beaten Clinton and served a second term.
Then what? Baker would have been 67 in 1996, and probably would not have been nominated. Having lost, Clinton probably wouldn't have been nominated a second time. My guess: Mario Cuomo with Bob Kerrey as running mate would have beaten a Republican ticket of Phil Gramm and Arlen Specter. Cuomo-Kerrey would win again in 2000 against Lamar Alexander and Jack Kemp.
9-11 would have happened as it did in our time, but instead of Gulf War II, Cuomo would have responded in a more piecemeal fashion, accomplishing as much as Bush did, but not being perceived as well. This would have resulted in Fred Thompson-Rudy Giuliani beating a Bob Kerrey-Evan Bayh ticket in 2004 and being reelected in 2008 against Dick Durbin and John Edwards.
And in 2012, Rudy Giuliani, running with Mitt Romney, would have beaten the Democratic ticket of Chuck Schumer and Ken Salazar and he'd be President right now.
No Clintons, no Obamas.
Now, it's your turn. Pick this to pieces.
NOTE! A commenter interpreted this post as my saying that Rumsfeld would have been a good President. NO NO NO! He would have been a terrible President, at least as bad as Bush the First. This is just an alternate history speculation about what would have followed if he had been President. Me, I wanted Pat Buchanan to be President.