He spent Wednesday beguiling the media and playing on the hopes of his final few candidates to build tension, drama and -- perhaps -- a climactic final plot twist.
Trump is on the cusp of making the most important decision yet in his short but explosive political career. He said late Wednesday that he will announce who will join him on the GOP ticket at 11 a.m. on Friday.
But despite his image as confident boardroom manager who delighted in decisively telling unfortunate saps "You're Fired," Trump has seemingly found the real-life quest for a political partner a little more difficult.
Indeed, he seems to be caught in a classic tug of love, between his heart — apparently yearning for a combative wingman like New Jersey Gov. Chris Christie — and his head, which may lean toward the more conventional political selection of someone like Indiana Gov. Mike Pence.
And in between lies former Newt Gingrich, the scrappy former House speaker esteemed for his political acumen and beloved for his off-the-cuff style.
"I'm narrowing it down. I mean I'm -- I'm at potentially four. But in my own mind, I probably am thinking about two," Trump told Fox News on Wednesday.
Trump's penchant for the unpredictable, of course, means the selection process remains fluid.
Further evidence of a potentially conflicted conscience: While he said Tuesday he wanted a running mate "skilled in hand-to-hand combat," he flipped the script late Wednesday, telling Fox News he actually doesn't need a vice presidential candidate in the mold of an attack dog.
Where the presumptive Republican nominee has been consistent is in finding a right-hand man with whom he'd be comfortable in the frenzied months of campaigning to come.
"Always, you have to say, 'Will that person be a good president?' " Trump told the New York Post last week
. "But for me, the most important thing is chemistry."
Trump orchestrated an extraordinary political drama on Wednesday -- though it was in part thanks to a blown tire on his airplane.
Trump's plane hit something when it landed Tuesday night, resulting in a popped tire, according to a source familiar with the process. That kept Trump in Indiana longer than he expected after campaigning with Pence and setting off a last-minute scramble of high-profile travelers to the Hoosier State as the clock ticked down on his VP decision.\
Making the most of his home advantage, Pence had Trump to breakfast at the governor's mansion after dining with him into the night on Tuesday. Christie was in touch with the billionaire by phone and discussed the vice presidency. Gingrich flew to Indiana on a jet financed by Fox News host Sean Hannity to press his case.
All the while, Trump was surrounded by the people he trusts most — his grown children, Eric, Donald Jr. and Ivanka.
Alabama Sen. Jeff Sessions, the first sitting senator to endorse Trump, also arrived in Indianapolis to counsel Trump on his choice.
"Believe me, he's putting a lot of thought into this. He's got some awesome, awesome people," Eric Trump told Fox News on Wednesday night.
After the day full of meetings, Trump headed off on a fundraising swing through California on Thursday ahead of his planned vice presidential unveiling Friday in Manhattan. The announcement of the newly minted ticket could mark an opportunity for Trump to build up a wave of momentum heading into the Republican National Convention in Cleveland next week.
Trump isn't just wrestling with his own competing impulses as he looks to make his pick. Those closest to him are also pulling him in different directions. His adult children, as well as son-in-law, Jared Kushner, have warmed to Pence, as has campaign chairman Paul Manafort.
But Trump's "gut" could be the wild card, and one source says: "Trump's gut is Christie."
Another source said Trump wants a "fighter" and Christie -- the tough talking former prosecutor -- fits the bill.
The New Jersey governor spent the day in back-to-back meetings in Washington as he leads Trump's transition team.
The abrasive Christie is not everyone's idea of an ideal political partner. But Trump, who puts a premium on loyalty, talks every day with the man who was the first big political beast to back him.
"I tell you, Chris Christie is somebody I've liked a long time; he's a total professional. He's a good guy, by the way, a lot of people don't understand that," he said.
A more conventional pick could be Pence, a selection that would put the minds of the party establishment at rest, given his experience in Washington and the Indiana governors mansion, and track record on conservative issues.
A source close to Pence told CNN's MJ Lee that when asked about the vice presidential race it "sure feels like Pence." But voting Trump's unpredictability note: "This is Trump we are talking about."
Trump, meanwhile, is doing all he can to stoke speculation about whom he will tap as his running mate, but little to tip his hand.
As he returned to his hotel Wednesday morning after breakfast with Pence, Trump returned reporters' questions about his meeting with his trademark thumbs up -- the same as he flashed a week earlier after Gingrich auditioned for the VP spot in Ohio.