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Rudy Giuliani Reportedly Spent Nearly $20,0000 On Cigars And Fountain Pens At The Depths Of His Depression

“Rock bottom” looks and feels different to everyone who experiences it. In the case of Rudy Giuliani, it is rumored to have involved a deep depression, heavy drinking binges, and nearly going broke — with an estimated $17,000 being spent on cigars and fountain pens over the span of six months.

This latest bit of intel, which The Daily Mail shared, comes from Andrew Kirtzman’s new book, Giuliani: The Rise and Tragic Fall of America’s Mayor. It’s not the first piece of hot gossip we’ve gotten from the book, which was released on September 13th. In the lead-up to its publication, we heard snippets of details about some of the stories it uncovered, including how Donald Trump allegedly refused to make Rudy secretary of state because of his drinking problem.

The biggest bombshell, however, gave a new insight into Donald and Rudy’s relationship. The book reveals that after riding the post-9/11 high of being named TIME’s Person of the Year and regularly referred to as “America’s Mayor,” Giuliani believed winning the Republican nomination for president in 2008 would be a cinch. But it wasn’t.

According to Kirtzman’s book, and interviews with Giuliani’s ex-wife Judith, Rudy went to a very dark place. And it was Trump, of all people, who helped lift his friend out of his depression and disappointment. “We moved into Mar-a-Lago and Donald kept our secret,” Judith told the author, adding that her then-husband was “always falling sh*tfaced somewhere.’”

While Giuliani eventually seemed to emerge from his depression, his stay at Mar-a-Lago didn’t exorcise all of Rudy’s demons. By 2013, the former New York City mayor was so broke that he ended up signing on to make infomercials for the identity theft protection service LifeLock. Ironically, people who signed up got a free document shredder.

What money did come into the Giuliani household was going quickly back out again. Kirtzman says that at one point, Rudy “blew $12,000 on cigars and $7,000 on fountain pens during one six-month period.” The one-time political force was now giving into his own “worst instincts” and was, according to the author, “professionally and politically adrift” in the summer of 2015, when Trump first approached him about endorsing him should he decide to run for president.

The rest, of course, is history — history still in the making — but does give some insight into why Rudy has regularly made a fool of himself to prop Trump up.

Giuliani: The Rise and Tragic Fall of America’s Mayor is on sale now.

(Via The Daily Mail)