Well, I know this is going to shock you… but the first thing Donnie Politics did after getting reelected wasn’t shaking hands with school kids or dunking on Nancy Pelosi… it was firing up his brokerage app. Because literally the day after his inauguration, Trump went on a bond-buying bender that’s already hit $103.7 million across 690 transactions. Let that sink in… six hundred ninety. (The man essentially took “I’m married to America” and turned it into “...and I also own her debt.”)

To really kick this off, let’s look at what he actually bought… because this wasn’t exactly Howard Marks’ slow-drip muni bond portfolio. Sure, Trump sprinkled in plenty of the classics: school boards, hospital authorities, airports, even the New York Triborough Bridge and Tunnel Authority got a swipe right from his account. 

But the real eyebrow raiser was how he went heavy into corporate bonds, which is basically lending money to the big boys at scale. We’re talking half a mil or more each into Qualcomm, Home Depot, T-Mobile, and UnitedHealth. And then, in a move so on-brand it almost feels scripted, he dropped $250K+ on Meta’s debt right after Zuck cut him a $1M inauguration check. (Call it “interest with benefits.” Somewhere, Zuckerberg’s whispering: “Please don’t ban Reels again.”)

Now here’s where it gets even more hilarious. Trump also scooped up bonds from megabanks like Morgan Stanley, Wells Fargo, and Citigroup… yes, some of the very same institutions he’s spent years accusing of refusing to bank with him after January 6th. And while he was busy playing creditor to the banks that once ghosted him, his administration was also reshaping the Fed… floating a Jerome Powell replacement and nominating Stephen Miran to the board. That means the same guy lending money to these banks is also handpicking the people who literally set interest rates, which directly determines how profitable those banks are.

The filings don’t show exact dollar amounts (only broad ranges) so that $103.7M is a minimum, not a cap. But here’s what they do reveal: Trump hasn’t sold a single bond. Not one. It’s been buy, buy, buy all year.

(Source: CNBC)

Which raises a bigger question: is Trump quietly signaling he thinks stocks are overpriced? When a guy sitting on $5.5B decides to shovel money into bonds (the khakis and New Balance of asset classes) instead of chasing equities, it says something. Maybe he sees the market as stretched, or maybe he just prefers clipping steady coupons to riding shotgun on whatever emotional fair ride Tesla’s stock is on these days.

And this is where we talk ethics. Every modern president since the late 1970s has divested their assets or tossed them into a blind trust. Carter sold his peanut farm, for crying out loud. Obama and Bush played ball. Trump? Shook his head, said “why the f*ck would I?” and became the first president since the 1978 ethics law to just keep riding his empire. Sure, federal law technically gives him cover. But let’s not kid ourselves… is there a bigger sure-thing bet than investing in something when you’re literally the guy signing the checks?

Watchdogs are, of course, losing their sh*t. CREW, the ethics group that’s basically Trump’s unwanted shadow, is pointing out that his setup lets him profit directly from decisions he controls. And they’re not wrong. If you’re throwing tariffs at supply chains with one hand and buying the bonds of the companies who benefit with the other, that’s a game so rigged you can’t lose.

Now let’s zoom out. Trump’s fortune sits at around $5.5 billion (Forbes’ number, not mine), which is up more than $3 billion since 2024 thanks to Trump Media, crypto-adjacent ventures, and his post-presidency hustle that Forbes literally called “the most lucrative in American history.” So $100M in bonds? That’s chump change. That’s the equivalent of you or me buying a share of Nvidia AMC. But it still shows he’d rather park his money in the corporate bond world than go all-in on stocks.

So essentially, Trump has made himself not just the leader of the free world, but also one of its weirdest and most eclectic bondholders. His portfolio now includes everything from hospitals and airports to Big Tech and Big Banks. Maybe this is Trump’s new version of patriotism: buy America, one bond at a time. Or maybe it’s just the latest season of Keeping Up With the Conflicts of Interest. Either way, the next time you’re paying tolls at a bridge or swiping your card at Home Depot, just remember… there’s a non-zero chance Donald J. Trump is on the other end collecting the interest.

At the time of publishing this article, Stocks.News holds positions in Tesla and Meta as mentioned in the article.