The mistake you're making
Is that you're assuming that President Trump actually has the inclination or capacity to make plans.
He doesn't.
In 2016 he did very well connecting with voters who didn't like or trust Hillary Clinton. Since being elected he's left the Paris climate agreement, the WHO, cancelled a nuclear proliferation treaty or two and shouted from the side-lines.
Where he's failed is on everything that needs planning: health care, North Korea, his response to Covid. Trump does not have the discipline or intellectual staying power to do anything long-term. Does he have the ability to gerrymander this election? No.