If the election were held today, most top Trump advisers believe it would look a lot like 2012 -- meaning an overwhelming Democratic victory. Yet they are actually upbeat.
Four years ago, President Obama won 332 electoral votes to 206 for Mitt Romney. The inside take at Trump Tower, among the political veterans, is that Trump is currently winning states with a combined 200 to 210 electoral votes.
So how can they be upbeat? The election isn't today -- it is 120 days away, and most of the key battleground states are very close. The thinking inside Trump Tower is that Hillary Clinton was unable to take advantage of Trump's spring missteps and missed opportunities.
Florida is one big priority for boosting Trump's numbers, and the big foundation for Trump's electoral strategy is the Rust Belt -- including traditionally blue Pennsylvania and Michigan.
As they set about their state-by-state planning, there is one internal complication: the candidate keeps insisting he can win California and New York. None of the political pros on Team Trump think that is evenly remotely possible, but word is the boss gets a little testy when told he is wrong.
2) POTUS heads to Dallas looking to bridge trust divide
President Obama heads to Dallas this week to pay tribute to the police officers killed in last week's horrific ambush.
And as he does, NPR's Steve Inskeep notes, the President faces a trust gap with some in law enforcement who do not believe he has always had their back.
"Whenever he speaks out showing concern about white officers killing black men, he's accused of being against the police. We've seen that in voter interviews; people do raise that concern. And so he'll have a special challenge as to how to address this concern about the safety of police as well as the safety of African-Americans on the streets."
3) Cruz 2020, with a Trump 2016 twist
It wasn't too long ago that Ted Cruz called Donald Trump
a pathological liar.
Now, the Texas senator is preparing to be one of the big speakers at Trump's GOP nominating convention.
Given the bad blood at the end of Cruz's presidential bid, it's a big deal. Remember, Cruz was furious when Trump suggested that the senator's father knew Lee Harvey Oswald, the assassin of President John F. Kennedy.
But CNN's Manu Raju says Cruz very much wanted a 2016 convention role as he looks ahead to 2020.
"Ted Cruz has positioned himself as the unapologetic leader of movement conservatives ... He has not agreed to endorse Donald Trump, but expect that to be almost a launching pad of sorts as he tries to position himself to be a possible 2020 candidate if Donald Trump does not win in the fall."
4) Can the delegates dump Trump? This week will give big clues
The main event is a week from Monday, but developments this week will tell us a lot about whether Donald Trump's convention will go smoothly.
The rules will be set this week, as well as other key preparations, and The Atlantic's Molly Ball says the drama includes many GOP activists who are determined to find some way to deny Trump the nomination.
"Multiple different groups trying to do this, trying to force a minority report out of the rules committee, and trying to get delegates to stand up in the actual roll call vote of the convention. The most pressure may be brought to bear on those delegates from the states at the beginning of the alphabet. Alabama, Alaska, Arizona, because the feeling is, if they stand up at the beginning of the roll call and make a statement, other delegates may be emboldened to follow them."
5) Want a scripted affair? Well then come back next election
Most presidential nominating conventions follow a traditional -- and predictable -- script.
The keynote address. The biographical speakers designed to build up the nominee. Showcases of party rising stars.
Sure, there will be some of that at Trump's convention, but Mary Katherine Ham of The Federalist suggests anyone who thinks they know how this is all going to play out is certain to be surprised.
"People keep asking, for instance, Speaker Ryan, 'Hey, you keep disagreeing him, but you endorsed him!' He's like 'Yup, that's correct.' And people keep thinking this story's going to change, and they're going to keep doing this dance for four months, and it's going to be weird, so get ready. "