God on Earth Trump rolled back vehicle fuel economy regs, to increase demand for gas. He repealed the incentives for EVs, to reduce alternatives to gas powered cars. He has pulled funding for wind and solar power generation programs, to increase demand for fossil fuel generated power. The regime tried to end the Energy Star program that promoted appliance energy efficiency. This regime is all about increasing demand for fossil fuels.

Sure. Trump hates Green Woke stuff. So do his voters.

That doesn't mean Trump hates low oil prices. Which is voters absolutely do not hate.

If you don't "pay off" for past bribes received, you reduce the probability of the same parties paying more bribes in the future.

So? That's never been Trump's MO. If you don't honor past contracts entered into, you reduce the probability of getting future contracts. If you don't abide by past trade agreements, you reduce the probability of getting future trade agreements. Etc. Trump doesn't care. He breaks deals all the time, he abrogates promises all the time, etc.

Plus, as your earlier recitation points out, the oil companies have already got their return. I'm sure Trump quite reasonably believes that the oil companies have already been well paid in full many times over. It's the approach he takes with all his supporters who aren't happy with how much they got in return for their support - Exhibit A being the anti-abortion right, who are livid that they aren't getting the policies they want and who Trump brushes off by telling them they should be grateful not to have Democrats in charge.

So, no. I think it's still utterly implausible that Trump actually wants oil prices to go up, and that he would be motivated at all to aim towards that goal out of some sense of obligation to the oil companies. Because he never feels a sense of obligation to anyone, and he isn't really in business with the oil companies the way he is with so many other Middle East interests.