This would never actually happen in real life, but let's say for the sake of argument that you're a 76-year-old white guy who has been around since the beginning of time. You held elected office for 46 years. You ran two spectacularly disastrous campaigns for President made notable by their brevity and startlingly incoherent babbling on the stump. You're identified with the Democratic Party run by large corporate donors. And you've got some dark things in your past. You spent weeks on national television abusing an African-American woman who dared to accuse a Supreme Court nominee of harassment. You supported forced school integration in the South but opposed it in the north. And you championed policies that led to the mass incarceration of black males.
You decide to run for President in a year when a new breed of progressives who refuse corporate donations has brought new energy to your party and when women and people of color are achieving unprecedented success in politics. You're facing a multitude of talented opponents. Most of them are aggressive progressives. Nearly all are decades younger. Several are women. Many are people of color.
What to do to make headway against this kind of tough current?
The situation calls for something bold and different. What about the classic Trojan horse ploy? It worked for Odysseus, your best pal back in prep school. Cast yourself in an altered form in order to slip through the 2020 gates. The killer move, obviously, would be to recruit a human shield in the form of a young, dynamic, brilliant, progressive, eloquent, African-American woman!
You only have to get past one little problem in order to pull off this brilliant con: convincing such a person that this would be the smart move for her.