It’s tough to endorse a Democrat, but when I found out my friend Whitney Tilson was running for mayor of New York City, I had to donate to his campaign. Whitney was one of the first people in the financial industry, back in the early 2010s, to be nice to me. And when it boils down to it, he’s just a decent guy.
Politically, the fact is that I disagree with Whitney on a lot of issues. He is an outspoken critic of President Trump and a fervent believer in the Democratic Party. But I always think of one of my favorite quotes:
"I never considered a difference of opinion in politics, in religion, in philosophy, as cause for withdrawing from a friend."
- Thomas Jefferson to William Hamilton, April 22, 1800
I know that New York City’s Mayoral race is definitely going to be won by a Democrat and at least I know Whitney to be a person of integrity and honesty. In my opinion, that already puts him ahead of most politicians, regardless of party.
The Far Left Has “Hijacked” The Democratic Party
Despite our differing political affiliations, I found it refreshing to hear Tilson’s perspective on pulling his party back from the fringes and offering a pragmatic, centrist approach to governance.
He wasted no time in addressing the political moment that led him to enter the race.
“In part, the reason I decided to run is the shock at what happened on November 5th. 90% of U.S. counties shifted toward Trump. And as a lifelong Democrat, that was a real wake-up call that we're losing the narrative. We're losing the middle class, the working class, pretty much every demographic. And it's because our party's in many ways gotten hijacked by the far left—a toxic combination of bad ideas executed badly. And certainly New York City would be exhibit A.”
"I'm determined to drag my party back to the center rather than abandon it. And so I'm running as the only person who's not a career politician in the race, the only person with a business background, to take it back from the career politicians and the special interests who have effectively run this city and are running it into the ground."
He emphasized his desire to bring New York back to the center and away from career politicians.
“I’m running as the only person who's not a career politician in the race, the only person with a business background. We are not in a death spiral for sure—New York’s an incredible city with incredible assets and we're still super rich—but we're clearly heading the wrong direction at an alarming rate.”
"This is a huge managerial job, and it's being run by people who aren't business people and don't understand efficiency and accountability and key performance indicators. Certainly, they have never cut costs in their lives, so I plan to do all of that."
Crime In New York City
One of the most pressing issues in the interview was crime in New York City, a topic that has become central to Tilson’s campaign. He laid out the stark reality:
“After decades of progress, five years ago, we were one of the safest large cities in America. Our violent crime rate was probably a third of Philadelphia's, for example. In the last five years, the seven major felonies are up 52% on average in this city. And felony assaults are at a 25-year high. Felony assaults on the subways are up 150%.”
Tilson traced the rise in crime to policy shifts within the Democratic Party.
“What really happened was Democrats flipped the New York State Senate back in 2018 and passed a lot of legislation like bail reform, discovery reform, and sort of excess sanctuary city laws. Basically, we took a lot of criminal justice reform good ideas and went way too far and decriminalized crime. And I want to make crime illegal again.”
"We as a party have become way too permissive on crime and disorder. We actually, believe it or not, this one will shock you—two years ago, the City Council passed a homeless bill of rights that put into law, quote, 'the right to sleep outside.' And my view is exactly the opposite."
He outlined his approach to tackling crime and homelessness:
Increase Police Presence – “We’re at a 34-year low in terms of number of police officers. We need to get that number back up, probably another 10% or so more police officers.”
Repeal the “Right to Sleep Outside” Law – “Two years ago, the city council passed a homeless bill of rights that put into law, quote, the right to sleep outside. My view is exactly the opposite. No civilized city should anyone have the right to sleep in the parks, streets, subways overnight.”
Overhaul the Homeless Services System – “It’s a very poorly managed system right now, and the good nonprofit providers are treated the same way, which is badly, as the bad providers.”
Keep Rikers Island Open – “The City Council's plan to actually close the island is going too far. I think we need to keep Rikers Island open but smaller.”
Reform Sanctuary City Policies – “We should be able to turn serious criminals over to ICE. Right now, that’s not happening.”
Economy, Markets and Crypto
Given Tilson’s background as a hedge fund manager, we naturally pivoted to the broader economic picture. We discussed the Federal Reserve’s current predicament and whether we are entering a period of stagflation.
“Big picture, the U.S. economy is actually doing quite well,” Tilson argued. “It's been consistently growing, so I don't believe we are in stagflation. Corporate profits are very strong. The latest quarter of GDP is growing nicely. Inflation, I predicted, would come down, but I don't think it’s going to hit the Fed’s 2% target anytime soon.”
However, he did acknowledge the risks of high stock market valuations.
“Stocks could fall 10% or 20% and still not be cheap. I'm a value guy. I'm sitting on 30% cash right now in my personal account, but I’m not rushing to sell my index funds or blue-chip stocks I own.”
On crypto, he was skeptical but open to blockchain applications.
“I’ve been skeptical of crypto as an instrument of speculation. I invest in things that produce cash flow. But I do believe in blockchain technology, and I want to make New York City a great place for all types of emerging technologies.”
Trump and the Legal System
I pressed Tilson on his thoughts regarding Mayor Eric Adams’ legal troubles and how they compared to the cases against Trump. He viewed the charges against Adams as weak but noted that further investigations might reveal deeper corruption.
When it came to Trump, however, he was unequivocal.
“On January 7th, after he tried to overthrow our democracy and murder his own vice president, he should have been locked up and never let out of prison for that crime.” While I challenged him on that characterization, Tilson doubled down: “He did incite a mob, organize and incite a mob to try and block the certification of an election that he knew he lost.”
We also discussed Trump’s civil fraud case in New York. Tilson admitted that particular case was one of the weaker ones against Trump, but argued that it was just one of many legal issues the former president faced.
Stepping Out Of The Echo Chamber
As we wrapped up, I took a moment to reflect on Tilson’s approach to markets, which I always admitted.
“I like short sellers because they're willing to look at both sides of the coin. And I think in any methodology for decision-making, whether it's in investing or politics, it’s an asset to not be afraid to lay all the facts out on the table.”
Tilson agreed.
“I think sort of both parties have moved away, and I’m doing my part to try and drag my party back to the center.”
For those interested in supporting his campaign, he made one final pitch: “Any US citizen can donate up to $2,100 at WhitneyForMayor.com. But particularly for any New York City residents, the city matches donations up to $250, eight to one.”
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