Why This May Be the Worst Bond Market in 200 Years — And What It Means for Your Retirement
One of the biggest financial stories in September wasn’t entirely unexpected, but it highlighted a major shift in the bond market nonetheless.

Today, the complete restructuring of our federal government and economy looks more like one of these jenga towers than a sound structure.
Adapting monetary policies for a changing world is never easy, but most people I speak to, from fund managers to clients and neighbors, feel overwhelmed. Almost everyday there is a cascade of new “deals” and systemic changes to policies across government departments. In some cases, we are given conflicting information. It’s confusing.
And,this is my personal judgement, I think it’s simply a fact that this is the least technically competent and least qualified administration of my lifetime. They aren’t even bringing their A-game because they seem more interested in impressing the president than effectively running their departments. Loyalty politics is never positive for the people, regardless of the party in power.
To me, the economy resembles a Jenga tower. We watch, daily, as block after block of the tower is pulled out. We wait for the tower to fall.
There’s no way to predict or project how the economy will react to each change. Too many interconnected variables are in play to adjust them all and determine the “end result” of where our economy will be a year from now, let alone a week from now!
This article delves into that interdependence. I want to discuss this tower, what these interconnected variables are, and reassessing risk in uncertain times.
.png)
From the top of the Jenga tower, you only see glimpses of single issues. Rising gas prices. Unemployment. Midterms.
As humans, it’s often easier to look at issues this way, too. It feels that they are easier to understand and “solve” if we compartmentalize them. But that has become impossible if we want realistic solutions.
Fiduciaries and advisors, I argue, can’t compartmentalize them effectively. To do so leaves our clients open to risk. It’s challenging to find a monitor big enough to display the big picture, but we must get as close as possible to provide well-researched financial advice.
Assets from commodities and gold to stocks, bonds, and real estate all hinge on a complex web of variables like those above. Many are economic. Moreover, these days these variables are increasingly political. More of them than I would like are becoming controversial. But that’s where we are.
It is easier to plan ahead if you can determine two things:
If nothing else: The underlying issue is information accuracy. It is challenging for professionals across the board to take data from the government at face value. Before diving into the Treasury, let’s review some of the past decisions that have made official data questionable:
All of this leads to financial-specific factors: The financial decisions under Secretary of the Treasury Scott Bessent, whom many, including myself, thought was initially more dependable given his extensive history in banking and finance. He exhibited restraint in the beginning of the President’s term, appearing to look at the fiscal situation with more gravity than others in the cabinet.
However, as national debt issues compound, it’s harder to trust his methodology. Let’s consider his recent focus of working to drop interest rates and collect investments in US Treasury bonds—an essential move to drop the yield curve. Typically, one would use long-term bonds here, because they are significantly more attractive.
Bessent is not doing that.
Instead, he’s buying back older bonds and releasing short-term bonds, saying this will help lower the debt.
But the debt is still $40 trillion dollars. And the obligations outpace revenue coming in.
In other words, it doesn’t matter if there are new, short-term bonds, because that income still can’t keep up with spending. Nevermind the fact that Treasury bonds require investors—investors that feel that the return is worth it. But short-term bonds offer lower rates in a period of high inflation and volatility, making them unattractive.
It’s not surprising that some experts are skeptical of Bessent’s strategy. And it’s not just about what he’s saying. Many are reviewing his most recent track record before entering the government.
Consider his hedge-fund, Key Square. Now, hedge funds are supposed to generate significant returns. But from the period he and his partner started with $500 billion in 2018 and when Bessent ran the fund on his own shortly after, the fund took a nosedive. By the time it closed in 2024, the fund had been reduced to $500 million.
Simply put: He lost 90% of his assets under management (AUM).
And the question arises: Is this someone we can trust to run the country’s Treasury?
Every day that we move away from financial stability, the more critical that question becomes.
There are dozens of moving parts after we consider that the foundation is shaky. Let’s try to connect several of them:
Now, all of these issues, from gas prices to the war and healthcare, are already shaky. Last year, we saw significant funding cuts across the board, weakening the systems. And if any of these already strained systems collapse, more may follow.

With so many variables, there are many ways the tower could fall. Please keep in mind that none of the below situations are verifiable at this point. This is a logic exercise based on the information we have today to show how issues are related and can compound:
These compounding challenges create problems for the administration. Any move, no matter well intentioned, can have dire consequences for the average American and investor.
Even if we cast all these problems and speculations aside, with the deficit like it is, a sell-off of US Treasury bills could shut the country down. We simply would be bankrupt—and unable to address all these compounding issues.
Unfortunately, many of these issues are connected. It is a weak and horrifying tower, almost designed to fall. Each passing day, in which policy does not change, it becomes weaker.
We can’t control the tower. But we must still consider risk. At the moment, the market and economy are volatile. That does not mean every worst-case scenario (described or otherwise) will happen. It means that it is prudent to be cautious.
I generally ask three things in regards to personal finance and wealth management during such emotionally charged periods:
These three questions act as levers to help you better manage your finances. It’s best to consider these questions deeply and use them to create plans for bear markets and bull markets—then don’t deviate without speaking with trusted advisors, friends, and family.
These are weird times. If you’d like a non-commitment, second opinion, please book a call with me today.
You can book a complimentary session
or call me at +1 (828) 884-8840.