Trump (surprised they didn’t hit that) - no new stimulus for unemployed, CORPORATE WELFARE MUST STOP, I WILL NOT BE RESPONSIBLE FOR MASSIVE DEFICITS, then pick a couple small cap companies that are going to receive massive boosts like the Kodak thing.
Tim Cook: Apple sales flagging, iPhone production issues due to supply chain issues
Take a bit of timing to get it right and be able to walk away from the markets relatively untraced (market trade interrogation is a useful way to trace inside information so hard to do in a way that leaves no trace but if you know you can perform your hack at leisure you can set up the initial trades well forward, wait for the market and some other external condition to walk into your ambush and then pounce
Best case he'd probably have a few tens of thousands in capital, and he gets one shot at it. In order to get the kind of leverage needed, he'd need to use short term options and/or move penny stocks. Either one of those would paint a giant target on him.