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it’s very different to say ‘‘I’ll extend medicade to all’’ vs ‘‘if I win this election I’ll cut you a literal check’’ there are different meanings here.
That’s not what he’s promising though. He’s promising to have a stimulus check passed through Congress. He’s not promising to personally write checks out of his own bank account.
This isn’t that complicated. The federal government has provided direct cash benefits across a myriad of times and circumstances. (Temporary assistance to needy families, farm subsidies, stimulus checks in several administrations, social security payments, etc.) These are all perfectly legal. And it’s perfectly legal to run for office promising to enact or expand such programs.
Plenty of what Trump does is illegal. This isn’t one of those time. It’s perfectly legal to run for office or campaign for your party saying, “I think people need money. If our side wins, we’ll give everyone a check.” Whether it’s good policy or not is another question. But the legality of it isn’t even debatable.