I don’t know exactly what Trump is going to say on Covid relief, but I have observed these types of Hill negotiations for a while.

Here’s what I’d guess happens.

What is the one thing McConnell can give Trump? A vote on the $2,000 check bill once it passes the House
That way, Trump can work the bill, get the votes if they are gettable.

And in exchange, Trump signs the Covid bill.

The House 2k check bill mandates that it only takes effect when Trump signs the large package
This way, Senate Republicans are on the record on the $2,000 check bill. It stands or falls on whether Trump can get 60 votes for it.
But the agreement would have to be agreed to like this: Trump signs the package in exchange for a vote on the $2,000 bill. Not Trump only signs if it passes. Govt shuts down tomorrow. Too much at stake.
The $2,000 check bill will divide Senate Rs. Most presidents would want to shield their party from this vote. But alas.
Congressional leaders can only guarantee process. They can never guarantee outcome, which is why this makes the most sense.
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