The legality of Trump's actions are dubious, however it would be stupid politically to try to take action to try to stop it. Trump is redirecting money earmarked for FEMA to pay for the enhanced benefits, so there is money appropriated, which means it isn't a guarantee Trump looses in court. If Trump were to be stopped, Congress would need to sue the Trump administration, which means democrats would own it. Democrats suing to stop the enhanced benefits would mean they would take the blame for the stopped benefits, the lock-downs would be even more unpopular (hurting down ballot elections).
I wouldn't be surprised to see republicans put up a fight as well since this is the kind of move conservatives have been campaigning on preventing forever. A few have already spoken out on it.
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Individual senators have no authority to challenge Trump's actions. Any legal challenge would need to come from the House as an institution, or the Senate as an institution. I am not sure what specifically can trigger a challenge by the Senate or the House, but it would likely start with leadership of the majority agreeing to want to take action, and there being a vote.
Pelosi and Schemer overplayed their hands in the negotiations. Biden meanwhile is in a tough spot, if he is supportive of Trump's actions, he is praising his opponent, however if he is critical of Trump's actions, he is seen as being against helping unemployed Americans.
Trump is trying to gut social security and decide what to do with the money on his own without congress. Seems pretty easy spot for democrats to me - nothing they do would really change the view of people who believe they are 'against helping unemployed Americans'.
In the end I think Trump is pissing off the Republicans by stripping congress of power and Democrats for going after social security.
Trump is making the issue of middle tax cuts an election issue. He is making it an election issue and will force Democrats to either agree that Trump is doing the right thing, or campaign on raising taxes on the middle class, both of which would hurt house Democrats, either with their base, or with moderates.
The payroll tax cut is an additional incentive to get back to work. If they were making $10/hour before the pandemic, they would now effectively be making ~$10.62/hour upon returning to work. The more people that return to work, the more opportunities of those without a job will have to get a job.
Trump is not gutting Social Security. In ~2011(?), when there was a temporary 2% tax holiday on social security taxes, Obama directed the treasury to put government bonds of equal value of the lost tax revenue into the social security trust fund, and I have every reason to believe Trump would do the same thing. Further, the difference between cutting the payroll tax and sending a cash payment to those who make under a threshold is a distinction without a difference, as in both cases it is the Federal government that needs to borrow to pay for it.