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President Colin Powell

The main obstacle is his reluctance to run for president and his wife’s even stauncher opposition to a campaign. It’s definitely not impossible, and the thought of having a moderate Republican president in the 1990s is interesting idea to play with.

Winning a Republican primary would be a bit difficult - Bob Dole nearly lost for not being conservative enough. Polls at the time showed Dole leading Powell by 32% to 30%. In the general election, Powell’s personal appeal would go a long way against Clinton; an exit poll conducted on Election Day had Powell leading by 12% after Dole lost by 8.5%. While this lead would evaporate as Powell became viewed as a more partisan figure, many of Clinton’s attacks against Dole would not work on Powell. Even without running, Powell’s approval rating went down from 71% to 62% between 1993 and 1995. Of course, you could easily use a Clinton-screw POD like the Monica’s Baby timeline did. There was also talk of Powell running as an independent, though I see this as less likely. One poll I found had him in second (Clinton: 37%, Powell: 32%, Dole: 24%) while another had him in third (Clinton: 34%, Dole: 29%, Powell: 27%). Roughly basing Powell’s support by state on his supporters’ 1992 preferences, the electoral map would look like this.

genusmap.php

President Bill Clinton (D-AR) / Vice President Al Gore (D-TN): 401 EVs, 37%
General Colin Powell (I-NY) / Senator Warren Rudman (I-NH): 79 EVs, 32%
Senator Bob Dole (R-KS) / Former Secretary Jack Kemp (R-TX): 58 EVs, 24%

To summarize, Powell would not be a shoo-in for the Republican nomination but would be uniquely suited to defeat Clinton in the general election.

you could also have the hamilton electors from 2016 somehow pull off a deadlocked election and get the house dems and a few republicans to vote for powell
 
Powell's biggest problem is that he's out of step with the Republican Party on key issues. He's a self-described Rockefeller Republican who is pro-choice, pro-gun control, and pro-affirmative action (and from 2008 onwards he's endorsed Democratic candidates). There's a lot of Republicans who simply won't vote for someone with those views (in particular someone who is pro-choice), and even if he does somehow win the primary it's easy to imagine that conservative Republicans will launch a third-party candidacy. It's also important to remember that Powell's tremendous popularity is the result of him being a decorated general who helped lead America to victory in the Gulf War, and people are considering him in that light. Once he runs for President he'd have to undergo the rigorous campaign process and get dragged down into the partisan muck. I think him getting nominated is probably the hardest part, but if he gets nominated he has a decent chance in the election (I would say that 2000 is his best bet).
 
Powell is probably fairly electable but the main blockage is that he simply didn't want to. When someone says no to elected office as often as he did, they're probably not going to do it. IIRC at one point his wife threatened to leave him because he semi-seriously considered running for president in the mid-nineties, both of them not unreasonably having big concerns about his and his family's safety as the first black person to make a serious bid for the presidency. He isn't going to run as an independent against Clinton, if nothing else because he obviously wouldn't win and he's unlikely to throw away his roots in the GOP for a third party for the sake of a third party run.

I feel like the most likely way to make him president is in 2000, getting chosen as an running mate by a successful Republican nominee who wants or needs to take a big risk, and then at some point in the next four years that Republican falls down the stairs or something.
 
He was fairly close to running in 1996. The AH community seems to have accepted his refusal on face value, but it's relatively disingenuous albeit with justification. He'd given serious thought to a campaign staff etc. The real break on it was his family, in particular Alma had suffered from depression for years and was utterly and totally opposed to being a political/campaign wife.

He'd also been preparing to align himself closer to the Republican mainstream on the issues had he ran, so the 'Rockefeller Republican' thing isn't worth much. He obviously wouldn't have ran as a Liberal had he done so.
 
I feel like the most likely way to make him president is in 2000, getting chosen as an running mate by a successful Republican nominee who wants or needs to take a big risk, and then at some point in the next four years that Republican falls down the stairs or something.

A possible path to that happening could be Carroll Campbell somehow winning the nomination in 2000 (maybe after being picked as Dole's running mate in '96 instead of Kemp?) and Powell ending up as his VP pick. A few years go by and Campbell is forced to resign due to his Alzheimer's diagnosis and then you have Powell as POTUS.
 
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