Arriving in Bedminster, New Jersey for an extended break, the president left behind a capital grappling with a Russia scandal and buffeted by extraordinary leaks from government officials.
He has also failed to seize any major legislative victories in his first seven months in office, and is at odds with several Republican lawmakers on multiple fronts.
The White House said Trump's Bedminster stay would be a "working vacation," and cited scheduled upgrades of the West Wing's creaky heating and cooling system during the steamy Washington summer as a reason why Trump was leaving town.
"The President will continue to work over the next two weeks," said White House spokeswoman Lindsay Walters.
A president taking time off from a hectic schedule is nothing new. But Trump's down time is in the spotlight largely because of his relentless criticism of Barack Obama's breaks from the White House.
He ripped into Obama in 2011 for playing golf and then heading to a 10-day vacation in Martha's Vineyard. "Nice work ethic," Trump tweeted at the time.
"Pres. Obama is about to embark on a 17 day vacation in his 'native' Hawaii, putting Secret Service away from families on Christmas. Aloha!," Trump posted two years later.
Not only did Trump attack Obama, he routinely told supporters he would eschew time off if he were elected because he would be swamped with work.
"I would not be a president who took vacations," he said in 2015. "I would not be a president that takes time off."
Despite his comments, Trump has taken considerably more time off than Obama in their respective first seven months in office.
According to a Washington Post tally, by the end of August Trump will have spent all or part of 53 days at leisure during his presidency, compared with 15 days for Obama through August 2009.
Much of Trump's time off took place at properties bearing his name.
At the height of negotiations over health care reform, Trump chided lawmakers by saying he could not imagine "that Congress would dare to leave Washington" without sending a new health care bill to his desk.
Trump ultimately failed to successfully broker a deal, the Republican health care reforms collapsed, and Congress shuttered Thursday for its month-long summer recess.
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