And his allies aren't helping, either.
Tuesday morning, from 6:30 a.m. ET until nearly 9 a.m., the President issued four statements via Twitter to decry the "Fake News Media," the Ninth Circuit Court of Appeals that once again struck down his travel ban and the former Attorney General Loretta Lynch's "protection" of his former Democratic rival, Hillary Clinton.
It wasn't until 9:29 a.m. that Trump got back on message, tweeting about his afternoon Wisconsin trip "to talk about JOBS, JOBS, JOBS!"
But by then, Trump had offered several story lines leading away from the White House's messaging, drawing attention back to the controversies that have dogged their policy efforts.
The self-sabotage is all too familiar in the Trump White House, where Trump -- ultimately his administration's chief messenger -- has blown up successive White House communications strategies, sometimes by directly contradicting his own spokespeople.
As fired FBI Director James Comey prepared to testify last week before Congress following a steady stream of allegations about the President's conduct, the White House tried to put its focus elsewhere: infrastructure week.
Even before Comey's testimony later in the week took the spotlight off the infrastructure plans, Trump tweeted about the travel ban his administration has been fighting to reinstate and continued an offensive against London Mayor Sadiq Khan.
Two days later, as White House officials struggled to return the focus to infrastructure week, Trump -- seemingly out of the blue -- tweeted that he had landed on a pick for FBI director, sending his White House scrambling. It would be hours before the White House put out an official press release on the matter.
By the end of the week -- without even counting Comey's testimony -- Trump had drawn attention to several storylines that had nothing to do with the administration's infrastructure proposals.
'Workforce development week'
The White House staff pressed forward again, billing this week as "workforce development week," hoping to once again use the power of the bully pulpit to draw attention to the administration's policy agenda.
"We can't turn off the Russia noise, but we need to do a better job filling the atmosphere with an alternative," a Republican involved in White House strategy said as the week began.
The White House also hoped to "keep President Trump busy" with projects and travel, including a trip to Wisconsin with his daughter, Ivanka, an administration official said.
Officials hoped that Ivanka Trump's involvement would make it less likely Trump would undermine the messaging of the week.
That hope was gone by Tuesday amid the slew of fresh distractions provided by the President's allies and, on Twitter, by the President himself.
"In theory, this shouldn't be hard. Your prime directive is to stay out of your own way. Politicians get in their own way with some frequency, but not in a daily or hourly fashion in the way we've seen from this White House," said Doug Heye, who served as communications chief for former House Majority Leader Eric Cantor and is now a CNN political commentator.
That has complicated the White House's task of proving to the public that it can focus on the issues that matter even as controversies swirl.
Ron Bonjean, a Republican strategist who helped shepherd Justice Neil Gorsuch through Senate confirmation, said it's key that the White House continues to focus on promoting its agenda despite the distractions, even those of the President's own making. The messaging may not break through the national news cycle, but it could still help the White House earn positive local coverage.
"It's very difficult to get the media to focus on your issues when there's so much turbulence happening, but you have to do it," Bonjean said.
But if the task is "walking and chewing gum at the same time," Heye said it's been complicated by Trump.
"It's more like trying to steer a car while holding off with one hand someone in the passenger seat who will grab at the wheel at every opportunity they get," Heye said.
Republican strategists working outside the White House frequently bemoan the tall task of White House communications officials and several have refused to consider what would normally be a coveted position inside the White House because Trump so consistently undermines his own communications shop.
"It's mission impossible," one Republican strategist close to the White House said of the press shop's job.