November 8, 2025
I should be feeling great. I spent Halloween weekend attending, not participating in, the Greenwich Village Halloween Parade, and then attending, not participating in, the New York City Marathon. Rather than seeing and experiencing the hellscape that the current President describes as a pretext for sending in the Marines, the National Guard, the FBI and ICE, I saw hundreds of thousands of joyous citizens celebrating what it means to be a New Yorker. People were singing, dancing, playing instruments, and parading under the watchful eyes of New York’s finest, who could not have been any nicer, more courteous, and more helpful under challenging conditions. Even Mother Nature was on board. People were partying like it was 1999, not 1929.
Then, on the following Tuesday, the Democratic (not Democrat) Party pitched a shutout worthy of Red Sox pitcher and hopefully Cy Young Award winner, Garrett Crochet. Democrats swept New York City, New Jersey, Virginia, Pennsylvania, Georgia, and California. It was like a pandemic that even had Robert F. Kennedy, Jr. looking for a vaccine. The two major issues were Trump and affordability. As it turns out, I am not the only one that has Trump Derangement Syndrome for which there is no vaccine. Nothing epitomized the tone deaf President more, other than “YMCA” by the Village People, was his Great Gatsby Party at Mar-a-Lago. How did the Roaring 20’s and “The Great Gatsby” wind up? His next party should have a King Louis XVI theme with a prize going to the best Marie Antoinette costume.
So why am I in a dark place? In the words of musician David Bromberg, “I must have someone else’s blues.” I just finished two books on the Great Depression. The first was “1929” by CNBC’s Andrew Ross Sorkin, and the second was “The Great Crash of 1929” by economist John Kenneth Galbraith. Because I am a glutton for punishment, I downloaded and started reading “Too Big to Fail,” by Andrew Ross Sorkin, which is about the Great Recession of 2008. Just as I was climbing out of my abyss, William Birdthistle, former director of the Division of Investment Management at the Securities and Exchange Commission, wrote a New York Times guest essay titled, “Trump is Pushing Us Toward a Crash. It Could Be 1929 All Over Again.” It’s back to the abyss.
One of the themes that all of these writers touched upon was the cheerleading optimism that the best and brightest financial minds had at the time despite all of the evidence to the contrary. A financial newsletter that I get recently cited five financial risks that you should be aware of, and why you should remain bullish. It noted high stock prices and valuations, a possible AI bubble, global instability, inflation and interest rate uncertainty, and high levels of debt. So what other parallels can we draw between the crashes of 1929, and 2008, and where we are today almost a hundred years later?
In 1929, regulation was almost non-existent. Investors believed in the infallibility of capitalism and the “invisible hand.” Insider trading was considered a virtue, not a crime. The Securities and Exchange Commission did not exist. Today, Trump is doing everything in his power to deregulate the financial markets. He has been busy firing regulators and tearing down guardrails. Not coincidentally, his machinations have benefited his family immensely.
Speculation was rampant in 1929. Everyone was on margin. Legal Ponzi schemes were created where leveraged vehicles similar to mutual funds could invest in other leveraged vehicles. In 2008, we had subprime mortgages being sliced and diced into unfathomable Collateralized Debt Obligations (CDO’s). Today, we have a feeding frenzy over anything that starts with the letters AI. And again, there is the mania over bitcoins, which one day may look like tulips.
Both periods were characterized by low interest rates, which fueled the buying of stocks on margin. Consumer debt and defaults today are at perilously high levels, and the Christmas season is just starting. Trump continuously browbeats the Federal Reserve and its chairman, Jerome Powell, to lower interest rates.
Banks prior to The Great Depression engaged in both commercial banking and investment banking. Risks taken by the investment bank put the entire bank and economy at risk. The Glass-Steagall Act of 1933, which separated commercial banking from investment banking, was essentially overturned in 1999 so that there is now no prohibition from commercial banks conducting investment banking activities. This was one of the major causes of the financial meltdown of 2008.
Mark Twain said “History doesn’t repeat itself, but it often rhymes.” There are many eerily similar things about today’s financial markets and economy that hearken back to an earlier day. Let’s hope that Trump and slump don’t rhyme.