United States presidential election, 2004
(✓) Senator John Edwards (D-NC) / Senator Joe Biden (D-DE) - 274 EVs; 48.5% of the PV
President George W. Bush (R-TX) / Vice President Dick Cheney (R-WY) - 264 EVs; 50.3% of the PV
President Bush gets a taste of his own medicine when he's defeated by John Edwards for reelection despite winning the popular vote. The almost two-point spread, however, hurts Edwards' legitimacy as President and he is unable to accomplish much of his campaign platform, including health care reform and a timetable to leave Iraq by 2008, before Republicans make gains in the House and Senate in 2006.
United States presidential election, 2008
(✓) Former Governor Jeb Bush (R-FL) / Governor Tim Pawlenty (R-MN) - 382 EVs; 53.0% of the PV
President John Edwards (D-NC) / Vice President Joe Biden (D-DE) - 156 EVs, 45.4% of the PV
Jeb Bush defeats John McCain, Mitt Romney and Mike Huckabee to become the Republican nominee in 2008. While Edwards starts at a disadvantage due to the situation in Iraq and signs of a weakening economy, the collapse of global financial markets in October 2008 propels Governor Bush to the largest victory for a Republican since 1984. John Edwards becomes remembered as another Democratic Jimmy Carter
United States presidential election, 2012
(✓) President Jeb Bush (R-FL) / Vice President Tim Pawlenty (R-MN) - 285 EVs; 50.1% of the PV
Senator Hillary Clinton (D-NY) / Senator Mark Warner (D-VA) - 253 EVs, 48.8% of the PV
Similar to OTL, President Bush's response to the financial crisis includes TARP and an economic stimulus packaged with tax cuts. He is also successful in passing a national charter school law, immigration reform, and national right to work. Economic recovery throughout his term is weak, and the situations in Iraq and Afghanistan remain precarious. Democratic Senator and former First Lady Hillary Clinton forgoes reelection and beats Barack Obama to become the Democratic nominee. She runs a campaign championing the middle class and decrying Bush's education and labor plans. Despite most pundits predicting a close Hillary win, Bush wins a second term by riding close victories in Iowa and Ohio.
United States presidential election, 2016
(✓) Former President George W. Bush (R-TX) / Senator Marco Rubio (R-FL) - 287 EVs; 48.0% of the PV
Businessman Donald Trump (D-NY) / Governor Dan Kildee (D-MI) - 251 EVs, 45.9% of the PV
Physician Jill Stein (G-MA) / Activist Ajamu Baraka (G-GA) - 0 EVs, 4.3% of the PV
2016 turns out to be one of the strangest years in American politics. Former President George W. Bush clears the Republican field of top-tier opponents, but faces a stronger than expected primary challenge from Idaho Governor Butch Otter. Running with a slogan of "Make American Great Again" and decrying American losses in trade and manufacturing, Businessman Donald Trump wins a fractured Democratic primary over Barack Obama, Deval Patrick, John Kerry, Bernie Sanders, and Amy Klobuchar. Unacceptable to many of the liberal base, Trump does poorly among college-educated Whites who flock to Bush and Green Party candidate Jill Stein.
I really like this scenario, possible (short) timeline in the works