Long before he tweeted about wiretaps, Donald Trump worried about who was listening in on his calls.
As a real estate mogul and reality TV star — well before he alleged on Twitter that former President Barack Obama wiretapped his phones during the campaign — Trump expressed regular concern that his phone lines were not secure, according to three former Trump Organization executives.
At times he talked about possible listening devices and worried that he was being monitored, two executives said. In other times, he was doing the monitoring. One of the executives said Trump occasionally taped his own phone conversations using an old-school tape recorder, although Trump once denied this.
"I assume when I pick up my telephone, people are listening to my conversations anyway, if you want to know the truth," Trump told conservative radio host Hugh Hewitt on December 1, 2015, when asked about NSA spying powers. "It's pretty sad commentary, but I err on the side of security."
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The former Trump Organization employees, whose collective tenure with the company spanned decades, detailed Trump's concern for surveillance on condition of anonymity because they feared retribution for disclosing internal practices.
A spokeswoman for the White House didn't return an email seeking comment on Trump's past use of, or concern about, possible surveillance.
Trump is hardly the only private businessperson concerned with security, experts said.
Rob Kimmons, a Houston, Texas-based private investigator who Trump hired to monitor the activities of another private detective his first wife had hired during their divorce, said wealthy individuals and businesspeople concerned about both thieves and competitors often engage in counter-surveillance.
"It's more common than people think," he said.
But to the former executives, Trump's recent accusations felt familiar.
The president claimed in a series of early morning tweets over the weekend that his predecessor in the White House had ordered that Trump's phones in Trump Tower be monitored in October, suggesting that "a good lawyer could make a great case" out of it. A spokesman for Obama immediately denied the claims and neither Trump nor the White House has offered any proof to substantiate them.
It wasn't the first time that worry was expressed. During his presidential bid, Trump campaign aides mentioned suspicions that their offices in Trump Tower were being bugged and that their communications were being monitored, though there was never any proof of that.
Others have claimed Trump recorded their own conversations with him.
In 2000, a reporter for Fortune wrote in a story questioning Trump's stated net worth that the then-real estate mogul "admitted he had begun taping" a conversation in which he threatened to sue the publication, a practice confirmed by one of the former Trump executives.
But when asked about tape-recording in a 2007 deposition by lawyers representing journalist Tim O'Brien, Trump denied he had done so, arguing he may have warned journalists that he would tape record in order to keep them honest.
"I think I might have said I want to tape," Trump testified.