RUMMY RUDY: Jack Smith team investigating Rudy Giuliani drinking problem

Rudy Giuliani has become a running joke in many articles because he’s so utterly hapless and meandering that it can be funny. Giuliani’s alcoholism, however, is not funny, and it is so pronounced that Special Counsel Jack Smith’s team is now investigating his profound drunkenness and whether it impacted Trump.

Smith is investigating how much Trump knew about Giuliani’s drinking and whether Trump should have trusted any of his legal advice.

The fact that Giuliani was so often extremely and obviously inebriated isn’t a legal defense for his behavior.

It is, however, possibly a mitigating factor for Trump, who plans to use the “following my lawyers’ advice” defense.

Smith’s team needs to know whether Trump knew he was sending a day drinker everywhere to investigate the election and advise him on legal strategy.

According to The New York Times deep dive:

“The office of the special counsel, Jack Smith, has questioned witnesses about Mr. Giuliani’s alcohol consumption as he was advising Mr. Trump, including on election night, according to a person familiar with the matter. Mr. Smith’s investigators have also asked about Mr. Trump’s level of awareness of his lawyer’s drinking as they worked to overturn the election and prevent Joseph R. Biden Jr. from being certified as the 2020 winner at almost any cost. (A spokesman for the special counsel declined to comment.)”

Obviously, Smith hasn’t charged anyone but Trump in the Washington DC case, so they will focus, as the article notes, on what Trump knew.

But in Georgia, Giuliani is a defendant, and his drinking will be his own problem in that jurisdiction.

It also seems as though the stress may be killing Rudy by fueling ever more drinking because Giuliani lost another attorney today when a motion to withdraw was filed this morning. (Judges must sign off on withdrawal of representation).

Report Continues below tweet:

This may leave the former NYC mayor without any legal representation.

Trump refuses to pay his former lawyer’s legal bills, which some of us think is a massive mistake because Giuliani is broke. Trump’s “fundraisers” for Giuliani don’t necessarily raise money to pay lawyers first — as exemplified by losing two of his lawyers.

RawStory reports:

“The former ‘America’s Mayor’ has faced significant financial problems over the past several years since the 2020 election, where he worked with Trump to try to overturn the election. Giuliani has been so plagued with lawsuits and criminal charges that he’s effectively gone bankrupt paying for his legal fees, earlier reports have indicated.”

Trump is making a massive mistake because Giuliani is so close to Trump (in the Georgia case and possibly the Washington DC case), and Trump is leaving him with no options other than to plead guilty with a proffer, “Rudy will testify to XYZ and plead guilty in exchange for no prison time and ABC.”

Trump isn’t reading the room. He knows that Giuliani’s drinking has made his behavior increasingly erratic and left him increasingly broke. An erratic and broke Giuliani is a dangerous Giuliani, at least to Trump and others in the Havana Room.

This column is based primarily on reporting by Maggie Haberman and Matt Flegenheimer of The New York Times.

I can be reached at and on X @JasonMiciak.

Editor’s note: This is an opinion column that solely reflects the opinions of the author.

Jason Miciak

Jason Miciak is an associate editor and opinion writer for Occupy Democrats. He's a Canadian-American who grew up in the Pacific Northwest. He is a trained attorney, but for the last five years, he's devoted his time to writing political news and analysis. He enjoys life on the Gulf Coast as a single dad to a 15-year-old daughter. Hobbies include flower pots, cooking, and doing what his daughter tells him they're doing. Sign up to get all of my posts by email right here: