Donald Trump's Hubris in the 1980s, His Mega Spending Spree the Same Year He Lost $1 Billion and More

The revelation over the weekend that Donald Trump lost nearly $1 billion in 1995, giving him a potential guard against paying federal income taxes for the next 18 years, has opened a door into a period of the Republican presidential candidate's past that he surely wishes remained shut. One former senior executive said he found nothing but failing enterprises in the Trump Organization. Others questioned how a CEO who went on a spending spree — a 727 jet for personal use, a new Manhattan skyscraper and other properties around the globe, among other things — could also claim a $1 billion loss the same year.

Top Stories

Donald Trump’s Business Decisions in ’80s Nearly Led Him to Ruin: "Abraham Wallach thought he had scored a major career break when Donald J. Trump hired him in 1990 for a senior executive role. Based on Mr. Trump’s boasting and gaudy lifestyle, Mr. Wallach imagined he would soon be leading impressive construction projects around the globe. Instead, he found an array of failing enterprises, he recalled on Monday. Many top executives had departed the Trump Organization, and those who remained were often huddled in closed-door meetings with bankers and whispering worriedly among themselves." (The New York Times)

Trump’s Tax Mystery Points Toward the Dealings Around His First Bankruptcies: "In 1995, Donald Trump was in the midst of a spending spree. He had recently bought a 727 jet for personal use, added a skyscraper to his Manhattan real estate portfolio and snapped up properties in Telluride, Colo., and Palm Beach, Fla., financial records show. That same year, he said he had negative $916 million in 'federal adjusted gross income,' a claim that gave him the prospect of avoiding federal income taxes for years to come. So how could he be thriving and avoiding taxes at the same time?" (The Washington Post)

New York Attorney General Sends Notice Of Violation To Donald Trump Foundation: "Donald Trump's charitable foundation solicited donations in New York state without the proper certification, a violation of state law, the state attorney general's office said in a letter sent to the Donald J. Trump Foundation. The letter, sent Friday and posted online by Eric Schneiderman's office Monday, demands that the foundation 'immediately cease soliciting contributions or engaging in any other fundraising activities in New York.'" (Patch)

From the Twitterverse

Trump adviser Roger Stone suggests that Hillary Clinton is "done" come Wednesday when a Wikileaks revelation is reportedly coming.

On the Radar

• Tim Kaine and Mike Pence will face off in the only vice presidential debate. Watch the live stream here at Patch!
• Hillary Clinton has two campaign events in Pennsylvania.
• Donald Trump has a rally in Arizona.
• Michelle Obama will attend two rallies in North Carolina.

Today's Numbers

• 34 days until Election Day 2016.
• Haiti is bracing for a deadly storm of 145 mph winds and as much as 40 inches of rain.
• The British pound hits its lowest point since 1985.
• Turkey purges 13,000 police officers over failed coup.

Quote of the Day

Michael Chertoff, Clinton's former prosecutor, on why he now endorses her:

"This issue came up at the debate about Miss Universe," he said. "Not only did he seem at the debate to lose his temper, but to get up at 3:30 a.m. and reach for your smartphone is to me a hysterical reaction. If you’re president, the button you reach for is not the Twitter button; it’s the nuclear button."

Allen McDuffee is a politics and policy reporter, investigative journalist, blogger and podcast host. He has written for The Atlantic, Wired and The Washington Post. Follow him on Twitter: @AllenMcDuffee

Photo credit: Gage Skidmore via Flickr Commons