But at this stage of his presidency, Trump is the least popular U.S. leader in modern times - even if his core supporters still fully support him. It was the first time the state had voted for a Republican presidential candidate since George H.W. Bush in 1988.
During an evening trip to Pennsylvania, one of the states that propelled his unlikely election victory, Trump planned to sign an executive order directing the Commerce Department and the US trade representative to conduct a study of USA trade agreements. The goal is to determine whether America is being treated fairly by its trading partners and the 164-nation World Trade Organization.
By day 99, he had signed 29 executive orders, more than any President in the last 72 years, except President Harry Truman who signed 57 orders in his first 100 days. He was then to hold a campaign-style rally in Harrisburg, the state capital.
In the midst of all the twists and turns, however, one thing has remained constant: the former reality TV star's obsession with the tube and twitter. That year, Ronald Reagan was recovering from an assassination attempt. Trump, she continued, has "started to chip away" at regulations, leading to a savings of an estimated $18 billion a year.
"It's a false standard, 100 days", Trump said while signing an executive order on Friday, "but I have to tell you, I don't think anybody has done what we've been able to do in 100 days, so we're very happy".
"There isn't a day that goes by that the president doesn't discuss some aspect of trade", Commerce Secretary Wilbur Ross said at the White House Friday.
The POTUS was also rebuffed twice on his plans to repeal and replace the "disastrous Obamacare", his predecessor Barack Obama's signature health care law.More news: "Star Wars: Episode IX" and new "Indiana Jones" movie get release dates
More news: D'oh! 'Simpsons' needle Trump ahead of 100-day milestone
More news: FCC chief lays out strategy on undoing 'net neutrality' rules
Despite an approval rating below 50 per cent, the unpredictable leader has come good on some of his promises, including withdrawing from the Trans-Pacific Partnership trade deal and allowing construction of the controversial Dakota Access Pipeline.
"A recent study found that 89 percent of the broadcast media's coverage of President Trump has been negative, even as objective measures indicate that Americans are feeling extraordinarily optimistic with President Trump at the helm", said Conway.
A ban on the entry of travelers from Muslim nations was overturned in the courts, while the promised construction of a wall on the Mexican border has hit roadblocks. Polls show that Americans feel slightly better about his job performance on that subject than his job performance overall.
"The first 100 days of my administration has been just about the most successful in our country's history", he said in his weekly address on Friday.
Earlier this week, Mr Trump announced his intention to work to renegotiate the North American Free Trade Agreement.
The executive orders signed on Saturday will mark Mr Trump's 31st and 32nd since taking office - the most of any president in his first 100 days since the Second World War.