The 100-day milestone has become a landmark for US presidents, a moment to measure the impact of the new administration - and a yardstick for things to come.
Since then, everything from travel bans to tough talk on North Korea has landed Trump's administration on the front pages. But, beyond the headlines, what has Trump achieved so far?
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There is a "giant contradiction" at the heart of Trump's first 100 days in office, say ABC's Shushannah Walshe and Rick Klein.
"Few modern presidents have accomplished so little in the opening months of their time in office," they write.
Trump has failed to make headway on key campaign promises - none more so than his attention-grabbing pledges to build a border wall with Mexico and refuse US visas to citizens of seven majority-Muslim countries, both orders effectively stymied by legal challenges.
And yet, the very nature of his first 100 days - chaotic, controversial, unpredictable - has fulfilled a "more basic promise" to his grassroots supporters, say Walshe and Klein: "He has redefined the office of president."
Trump is far from the first president to make missteps in his first months in office, says CNN's David Gergen. The real worry is that he keeps making the same mistakes.
As the 100 day mark nears, the Trump White House is still characterised by "deception", "internal struggles", "sliming of opponents" and "lack of strategy", says Gergen. The administration's learning curve appears "a lot flatter than it should be".
On the contrary, writes conservative commentator Kayleigh McEnany in The Hill, Trump has amassed a "significant resume of accomplishments" considering that the Democrats have been obstructing his administration every step of the way.
While the media has focused its glare on "gossipy, salacious stories" about goings-on inside the White House, the President has "signed more legislation and executive orders than any president in the past five decades", she writes.
However, the substance of Trump's achievements may actually prove to be irrelevant, says Politico's Michael Kruse - the property mogul has "made a career of convincing people that his failures were the exact opposite".
None of Trump's many business failures have ever shaken his conviction that he is a success, and so far none of his political misfires appear to have had a humbling effect, either, Kruse writes.
Most telling of this attitude is Trump's response last month to a Time reporter who quizzed him on his performance: “I can’t be doing so badly,” he said, "because I’m President, and you’re not."
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