He would even strip his own bed and let housekeeping know when he wanted his sheets washed, Wolff says in a set of unsourced claims.
An excerpt of Wolff's book ran on Wednesday in New York Magazine as other tidbits began to leak elsewhere in news publications that obtained advance copies.
Wolff writes that Trump was often the source of the embarrassing information that was later printed about him, complaining day and night on the phone to people he should not have trusted.
"He was a river of grievances, which recipients of his calls promptly spread to the ever-attentive media," Wolff's excerpt says.
In one call, on February 6, Trump complained about New York Times reporter Maggie Haberman - "a nut job" - columnist Gail Collins - "a moron" - and CNN chief Jeff Zucker, who he said was "made by Trump."
Trump also complained about a Time magazine cover that branded Steve Bannon the shadow president.
"How much influence do you think Steve Bannon has over me?" Trump allegedly said. "Zero! Zero!"
The president berated his son-in-law Jared Kushner in the same vein during the 26-minute call, the acquaintance of Trump supposedly told Wolff.
After the excerpt ran, Trump issued an extraordinary statement bashing Bannon, who went on the record to Wolff.
Trump's White House press secretary sent out a statement of her own that called the book "trashy tabloid fiction" full of "false and misleading accounts."
After the president's longtime consigliere was quoted trashing Donald Trump Jr. and claiming his father would have immediately been made aware of an infamous Trump Tower meeting with Russians.
Bannon claimed a Trump Tower meeting with a Russian lawyer, supposedly to obtain unflattering information about Hillary Clinton, was "treasonous" and "unpatriotic," prompting an unprecedented brushback of the former White House aide from the president.
"Steve Bannon has nothing to do with me or my presidency," Trump said in a statement provided by the White House that torches his former chief strategist. "When he was fired, he not only lost his job, he lost his mind."
Trump's press secretary, Sarah Huckabee Sanders, then told reporters that the president was "furious" and "disgusted" by Bannon's assault on the president's son and son-in-law, Jared Kushner, who also attended the Trump Tower meeting.
The White House's full-scale attack on Bannon, who was once one of Trump's top advisers, was ripe with personal slights, exposing a dramatic rift between the president and the conservative provocateur who is also the Breitbart News executive chairman.
It followed Bannon's comments undercutting the president's eldest son and a suggestion that Donald Trump was involved in the 2016 meeting with a Kremlin-linked Russian lawyer that Bannon is now quoted as saying should have been reported to the FBI.
"Steve was a staffer who worked for me after I had already won the nomination by defeating seventeen candidates, often described as the most talented field ever assembled in the Republican Party," Trump said. "Now that he is on his own, Steve is learning that winning isn't as easy as I make it look."
Trump said Bannon "doesn't represent my base, he's only in it for himself" and "had very little to do" with his victory, but "everything to do" with the loss of the Alabama Senate seat.
The cutting statement went on to say, "Steve pretends to be at war with the media, which he calls the opposition party, yet he spent his time at the White House leaking false information to the media to make himself seem far more important than he was."
Bannon backed losing candidate Roy Moore, who Trump ultimately campaigned for in the special election after claiming the Republican would have a tough time winning the general election and endorsing his primary opponent.
Sanders said Wednesday that the loss contributed to the falling out between the president, who last spoke to Bannon sometime in early December.
Accusing the president's son of treason is also not a way to "carry favour" with Trump, she stated, calling the allegation "ridiculous."
"I think there are a number of factors that played in," she told DailyMail.com. "I would certainly think that going after the president's son and an absolutely outrageous and unprecedented way, is probably not the best way to curry favor with anybody."