The Phlip Side: The Democratic Donald Trump

We have a narcissistic egomaniac running for office this year.  A man with ethical questions plaguing his professional career. A man who has displayed appalling behavior towards members of the opposite sex.  Someone who lacks the temperament to hold the office which he seeks.  If you think I am writing about Donald Trump, you would be wrong despite the fact that he does fit the description pretty well.  I am talking about fellow Democrat Alan Grayson.  Alan Grayson and Donald Trump are bosom buddies though, and are so similar in so many ways that I am not out of line in saying that Trump and Grayson are each other’s brother from another mother.  Both men, and I use that term loosely, are deeply flawed candidates whose campaigns are destined to fail.  Few elections, though, have candidates like Trump and Grayson who are a complete embarrassment to their respective political parties.

Narcissism is nothing new in politics, but Alan Grayson and Donald Trump take narcissism to a whole new level.  Trump’s obsessions with putting his name on everything, with his poll numbers, and with anyone who doesn’t worship at the tower of Trump (pun intended) provides ample evidence of his narcissism.  Grayson seems like he is going for the gold on this one though.  One doozy is the fact that Grayson thinks that bestowing his name on his now wife will make her a shoo in for his congressional seat.  The most galling example of Grayson’s narcissism is his failed attack on Harry Reid.  Reid met with a group of Congress(wo)men to coordinate strategy, and Grayson proved that the only person he cares about is himself.  Grayson could have used the meeting to try and move the ball forward on gun safety legislation, the Supreme Court vacancy, immigration reform, or a myriad of other issues.  Instead, he rudely yelled at Reid to say his name.  So, we know that Grayson values himself and boosting his massive ego over actually helping the people of Florida.

Grayson’s narcissism bordered on delusion when he sent an email that was entitled:  “You come at the King, you best not miss”.  What is Grayson the king of exactly, except maybe Congressional ethics violations.  Grayson has less Democratic institutional support than Nan Rich did in her campaign for governor.  Grayson laughably claims that the reason establishment Democrats don’t support him is because he is fighting the establishment, but as a member of Congress he IS an establishment Democrat.  His peers have simply rejected him in surprising, and rare, unanimity.  Even the quixotic campaign of the Democrat running against Debbie Wasserman Schultz has an endorsement from Bernie Sanders, which is one more endorsement from a member of Congress than Grayson has by my count.  The Reid incident and calling a reporter a shitting robot proves Grayson lacks the temperament to be an effective US Senator.  He sluffs it off as not always being polite, which is the same as Trump bashing political correctness, as they both try to excuse their unacceptable behavior.

The similarities between Alan Grayson and Donald Trump extend to their professional lives too.  Donald Trump has multiple bankruptcies and is being sued for fraud over Trump University.  The House Ethics Committee said that there is “substantial reason to believe” that Alan Grayson broke the law with his Cayman Islands Hedge Fund.  Donald Trump was rooting for the financial collapse under George W. Bush because he wanted to profit off of it.  Marketing materials for Grayson’s Cayman Islands Hedge Fund touted that, “the time to buy is when there’s blood in the streets.”  I am not going to try and score political points off of the tragedy in Orlando by snidely asking how Grayson turned a buck off of the bloodshed as I hope he realizes that using that particular quote was a grave mistake.  I do wonder if Grayson realizes though that the bloodshed that he brags about profiting from in other parts of the world is somebody’s home too.

Trump’s grotesque objectification of women, and his improper statements about women are both well documented and too voluminous to thoroughly delve into here.  The fact that Trump is a sexist isn’t in doubt.  The one thing that is in doubt is whether Trump would ever treat a woman as despicably as Alan Grayson treated his wife of more than two decades.  Grayson’s actions toward his former wife were beyond deplorable.  Grayson tried to get his ex-wife arrested for buying food for their children.  Grayson’s lawyer said that it wasn’t Grayson’s issue that his children lived in a house filled with mold.  Even though he is a multi-millionaire, he hoarded the family money so that his wife and kids were forced to go onto food stamps to eat.  There is a special place in hell for people who risk the health, welfare, and safety of their children just to get back at the person they are divorcing like Alan Grayson did.  I just hope that, like the Trump kids, the Grayson children grow up to be outstanding adults despite of who their father is.

Grayson started his campaign by admitting that he would not have run for US Senate had Marco Rubio run for re-election.  Now that it seems likely that Rubio will run for a second term in the US Senate, after a failed presidential campaign, Grayson has a decision to make.  Grayson can either write an eight figure check to his campaign to try and beat Patrick Murphy, or his baggage will weigh him down in what will be a humiliating double digit defeat.  Even if Grayson decides to spend most of his net worth and writes an eight figure check he would still be the underdog to win the Democratic Primary.  Should he defy the odds and beat Patrick Murphy, and his dumpster fire of a campaign makes that incredibly unlikely (which I put squarely on Grayson himself and not his campaign staff), he would only ensure that we are stuck with Marco Rubio for at least six more years.  Grayson is the poor man’s Trump, and it is only a matter of time before both campaigns go down in flames.

(Author’s Note: Please feel free to send any comments, suggestions, column ideas, or hate mail to

Sean Phillippi is a Democratic strategist and consultant based in Broward County.  He has worked for campaigns on the federal, state, and local levels, including the Florida Democratic Party and the Democratic Congressional Campaign Committee.  Sean is the Managing Member of TLE Analytics LLC, the political data and consulting firm he founded in 2012.


  1. A swing and a miss. If you want to do a hit job on a real progressive, you better come up with something more plausible than linking Grayson to Trump. If your motive is to get a real job with the establishment, you better keep to number crunching and give up on political commentary.


    1. LMAO my friend! I notice you call didn’t correct anything I said, because all of the crazy things Grayson has said and done are objectively true. I backed up my statements with facts, and formed my conclusion based on those facts. I will give Grayson credit though in that he was very polite and gracious when I went up to him Saturday, introduced myself (we have met before, but I wasn’t sure he knew who I was), and shook his hand.


      1. I won’t bother getting into a mudslinging fight. If you want to talk about the effectiveness of Grayson as a legislator and advocate of seniors and the middle class vs. the the ineffectiveness of Murphy as a legislator and a puppet for the bankers and the 1%, then let’s debate. Murphy is so afraid to debate Grayson he’d rather face him on the golf course.


  2. Maria Sachs · ·

    Sean is the best!!


  3. Publius Khan · ·

    Two years ago telling you Nan Rich had no support fell on deaf ears. Now it’s an argument against Grayson. I guess your only loyalty is to who pays you.


    1. Nan Rich had a lot more support. She had several current and former members of the Florida Legislature who endorsed her. She even had the most recent serving Democratic Governor of Florida endorse her. Grayson has zero current or former members of Congress supporting him from what I can tell.

      Also, Sen. Rich has ethics that are beyond reproach, and she has endorsed Rep. Murphy by the way. Grayson had an ethics investigation from the House Ethics Committee about his Cayman Islands Hedge Fund that concluded that there is substantial evidence that he broke the law.


  4. JOE KREPS · ·

    Grayson is one of the most accomplished legislators in Congress. I trust him to fight for seniors and the middle class. I do not trust Murphy. Also, Sean, you of all people should know what happens when you give the Democrat electorate a former Republican to vote for. Especially one who voted and contributed to Mitt Romney.


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