I wrote a very brief outline for another thread about Hillary and Trump facing down for NY Governor; basically my plot was Trump getting successfully courted by the GOP to run to replace Pataki in '06. Hillary challenges him in 2010.

Enter a more jaded Hillary Clinton who thanks to butterflies refuses Obama's offer to be SecState and instead seeks to launch a comeback in 8 years time, ruling out a primary challenge in 2012 and would instead look to 2016 to either succeed Obama or defeat whoever might beat Obama in 2012. With Trump likely not handling the recession very well; Hillary sees an opportunity to cap off nearly a decade of Senate service and put possibly six years of executive experience under her belt before 2016 and challenges Trump in 2010. I think we can all assume that 2010 won't be the Democrat's year in general, but like in OTL a Democrat will still pull off a win in New York and we now have once again that unlikely match up of Hillary Clinton vs Donald Trump.
 
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