Obama has said repeatedly he doesn't believe the billionaire real estate mogul will succeed him. But he has nonetheless instructed his staff to undertake exhaustive efforts to ensure whomever holds the office next, Republican or Democrat, has a clear view of how the federal government operates before voters even head to the polls.
The presidential transition process reflects a key facet of a functioning democracy, especially when outgoing and incoming commanders-in-chief are ideological opposites. It's that view, officials say, which has driven the President to ensure his staff leave behind an extensive blueprint for his successor.
It's a daunting task: an administration has upwards of 4,000 political appointments to fill across hundreds of agencies and offices, each contributing to trillions of dollars in federal spending. Routine paperwork, if not completed properly, could affect millions of Americans' daily lives. And specifications for military deployments overseas will require some degree of continuity, even if an incoming executive vows to change course once in office.
"It's an immensely challenging and complex process that takes a lot of time to do right," said Max Stier, the president and CEO of the Partnership for Public Service, a nonprofit, non-partisan organization that's working outside the federal government to foster an effective transfer of power. "Everyone that's starting now should feel like they're starting behind, because they are."
It's those concerns that prompted Obama to insist his staff begin planning for the transition well before either party's presumptive nominee emerged. His chief of staff, Denis McDonough, gathered cabinet secretaries and senior White House staffers in early March, tasking them with developing transition plans using their knowledge of agency operations over the past eight years.
The effort has included consultations between current White House officials and staffers who served in President George W. Bush's administration, who Obama aides laud as having provided an effective blueprint for their own transition to power in 2008 and 2009.
Obama's budget chief, Shaun Donovan, instructed federal agencies in April to begin compiling technical information to help guide the next administration's budget proposals. Those reports are due in September, two months before the general election.
White House officials are already beginning to transfer electronic records to the National Archives and Records Administration for preservation, a large-scale, legally required task the Obama administration is commencing earlier than past presidencies.
And last week, Obama established a pair of high-level councils meant to institutionalize the transition process, a move Congress insisted upon after years of loosely guided changeovers that varied widely in rigor.
The White House Transition Coordinating Council is headed by McDonough, with input from a variety of White House departments, including the National Security Council, the Office of Management and Budget and the National Economic Council. A second panel, the Agency Transition Directors Council, is meant to ensure the federal government's various arms are coordinated in their transfer-of-power plans.
The councils will begin meeting in the coming weeks to formally discuss the transition process, a White House official said, as both Democrats and Republicans conclude their nomination contests.
Trump, who's already emerged as the presumptive GOP nominee, said Monday he was assigning New Jersey Gov. Chris Christie to head his transition team. The businessman's campaign said the move was in line with other "critical steps to gear up for the general election against potential Democratic nominee Hillary Clinton, or whoever."
Clinton's campaign, meanwhile, hasn't named any official transition coordinators as she continues to battle for the Democratic nomination against Sen. Bernie Sanders, who also hasn't made public any plans for a presidential transition.
Once this summer's nominating conventions conclude, representatives from each campaign will begin meeting with current administration officials to begin the step-by-step process of ensuring nothing is overlooked once a presidential victor emerges in November.
That includes beginning classified intelligence briefings, which the White House said last week would start when the conventions have concluded. For Obama, that will mean allowing his intelligence experts to divulge government secrets to Trump, a man whose judgment and foreign knowledge he's repeatedly questioned.
White House Press Secretary Josh Earnest said Director of National Intelligence James Clapper has ultimate discretion on what exactly is contained in those classified sessions. Asked whether Obama had any concerns about Trump receiving classified material, Earnest said only that those assessments that will have to be "made by the intelligence community."
Clapper told reporters last week his agency has "already established a plan for briefing both candidates when they are named, and certainly after November when the president-elect is known."
"We already have a team set up to do that, and a designated lead, who is not a political appointee," Clapper said. "We normally arrange those depending on the candidates' schedules and where they are. We normally will accommodate their needs through a local secure facility."
Even before those briefings, though, advocates for effective transitions say candidates and their campaigns must begin conversations with the federal entities that will facilitate the presidential changeover. That includes agreeing on some basic details, like where to house a transition team and how to outfit the office space.
All of those particulars require a unit that's separate from the team tasked with actually winning the campaign, said Stier, whose group organized a meeting among both Republican and Democratic campaign officials last month to plot out how a successful transition might look.
"'Now what?' is not something you want a president-elect to be asking the day after the election," he said.