He'll have to decide if he's willing to hold a vote ahead of the election at a time when putting anything in the ballpark of $2 trillion is going to fracture the GOP and force members to say no to something that could benefit their constituents and buoy President Donald Trump -- even if the price tag is far more than they are comfortable with.
It's the same negotiation that has been happening for months, and yet with less than two weeks to go until the election, the stimulus talks have become a litmus test for just how much GOP loyalty is left for a President who is sinking in the polls. After years of sticking with Trump despite his antics and the fact that some of the President's policies flew in the face of long-established GOP orthodoxy, the stimulus bill is the make-or-break moment where Republican senators may finally throw up their hands and tell Trump "no."
The negotiation, according to the negotiators
If you are paying close attention to Pelosi's tone over the last few days, you'll notice she's much more upbeat about a deal than perhaps we've seen in weeks or even months. Suddenly what was a deadline of Tuesday evening to strike an agreement has stretched into Wednesday and perhaps will stretch even further into this week.
"Our conversation provided more clarity and common ground as we move closer to an agreement. Today's deadline enabled us to see that decisions could be reached and language could be exchanged, demonstrating that both sides are serious about finding a compromise," Pelosi wrote to her colleagues Tuesday evening.
Democratic House members who have been impatient with Pelosi's negotiation and her intention to wait for the White House to capitulate on nearly every one of the Democrats' priorities are watching closely with awe as they see their speaker get one concession after another from the White House.
As one Democratic member put it to me, questioning Pelosi's negotiating tactics isn't really a game worth playing and this moment is illustrating exactly why.
The Mnuchin factor
Mnuchin wants a deal. He's backed by a President who badly wants a deal in an election in which he is treading water.
And that's making Republican members on Capitol Hill very nervous about just how much they are willing to give.
The Treasury secretary is the one-man negotiator right now. After months of negotiations where White House chief of staff Mark Meadows was pulling the talks to the right and keeping the topline price tag well below where Democrats had been, Mnuchin is negotiating with Pelosi now in the ballpark of $2 trillion. Remember, that's just a few billion off where Democrats' $2.2 trillion proposal was and light years away from the $500 billion proposal that Senate Republicans are voting on later Wednesday.
In other words, that fact alone has left Republican senators signaling every way they know how that that price tag is just too high. Sen. Mitt Romney of Utah said this week even he wouldn't envision supporting something like that.
To say that Republicans don't trust Mnuchin might be an understatement. Republicans watching this negotiation have bemoaned over the last several days that every time they turn around, it feels like Mnuchin has given Pelosi a key concession. Asked about what Republicans are getting in return, one GOP aide said they were still waiting to hear.
"He's been very good because he's got a decent working relationship with the speaker and he's about the only one. Obviously, the President is aiming higher than we would. I don't know if it is about trust as much as there just isn't an agreement," Sen. Kevin Cramer, a Republican from North Dakota, put it delicately.
The McConnell factor
Almost nothing about a last-minute, $2 trillion stimulus deal would be helpful right now for McConnell.
For one, any vote on a package above $1.5 trillion is going to expose deep party schisms. Any deal now would come before an election in which conservatives were counting on a Supreme Court nominee to be the last major action to motivate their voters. Any agreement would force vulnerable members like Cory Gardner of Colorado, Thom Tillis of North Carolina, Joni Ernst of Iowa and Lindsey Graham of South Carolina (yes, he, too, would have to make a tough call on this) to decide whether they stand with Trump -- who is calling for this deal -- and the reality that many members think that another $2 trillion package is far too much money.
It's why McConnell said privately Tuesday during the GOP lunch what he has been signaling for months: he doesn't want Trump to cut this huge deal right now before the election and he has made it clear to the White House how he feels.
McConnell still said he would consider any legislation Pelosi and Mnuchin actually agree to, but he did not promise if a vote would happen before the election.
Negotiations, according to everyone else
GOP leaders in the Senate still believe that Pelosi and Mnuchin, despite all the happy talk, are still far from pulling this off. Aides involved and familiar with these discussions tell CNN that there are still vital chunks of information that is missing.
On Monday, aides struggled to understand what exactly Pelosi and Mnuchin had decided on when it came to rental assistance. As of Tuesday evening, there still wasn't much clarity.
Questions about how to handle liability insurance, unemployment insurance, how much exactly has been agreed to on state and local funding -- it's all still unclear to the people who will have to sit down and write this legislation.
GOP leadership aides and some Democratic aides involved tell CNN that they just don't see that as much progress has been made as Pelosi and Mncuhin are laying out right now. Again, that doesn't mean a deal can't come together very quickly if the White House and Pelosi sign off, but right now they are not there yet.
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