You don't pay 23.8% cap gain tax every year on the principal amount, but you do pay interest every year. Need to consider investment growth rate vs int rate potential capital calls if collateral declines. No?
This is a no brainer.
Here’s why.
The “buy, borrow, die” strategy is the single biggest loophole in the American tax code, and Ackman just proposed the cleanest fix anyone has ever put forward.
Let me walk through the mechanics.
Step 1: You build $10B in company stock. You never sell it. No taxable event occurs because capital gains only trigger on realization.
Step 2: You need $500M to buy a yacht, fund a foundation, or just live large. Instead of selling stock and paying 23.8% federal capital gains, you walk into Goldman Sachs and borrow $500M against your shares at 5-6% interest. Under federal tax code, loan proceeds are not income. You now have $500M in liquid cash and owe zero income tax.
Step 3: You keep borrowing. Year after year. The interest payments are trivial compared to the tax savings. A 6% interest rate on $500M is $30M annually. The capital gains tax you avoided? $119M. You’re saving $89M per year by borrowing instead of selling.
Step 4: You die. Here’s where the magic happens. Your heirs inherit the stock at “stepped-up basis,” meaning the cost basis resets to current market value. That $9.9B in appreciation that was never taxed? It vanishes from the IRS’s perspective forever. Your heirs sell a small slice to pay off your outstanding loans, keep the rest, and start the cycle again.
This is generational tax avoidance at scale.
Elon Musk had 238 million Tesla shares pledged as collateral in a 2024 SEC filing. That’s one-third of his total holdings. Larry Ellison has $24 billion in Oracle stock pledged. The research firm Audit Analytics found Musk’s pledged shares alone account for more than a third of all shares pledged across the entire NYSE and Nasdaq combined.
These aren’t edge cases. This is standard operating procedure for anyone with nine or ten figures in appreciated stock.
Now here’s what Ackman proposed:
If you borrow against company stock in excess of your cost basis, treat the loan as a deemed sale for tax purposes.
Example: You bought $100M in stock. It’s now worth $1B. You borrow $600M against it. Under current law, you owe nothing. Under Ackman’s proposal, you’d owe capital gains on $500M because that’s the amount exceeding your basis.
The IRS would treat it as if you’d sold $500M worth of stock. You’d pay the 23.8% federal rate. You’d still have your shares. You’d still get future appreciation. But you couldn’t extract the economic value of gains while pretending no realization occurred.
The elegance is in what this proposal avoids.
Wealth taxes require annual valuation of every asset, including illiquid private companies, art, real estate. The compliance costs are enormous. The legal challenges are real. The constitutional questions around taxing unrealized gains haven’t been settled.
Ackman’s approach sidesteps all of that. It doesn’t tax wealth. It doesn’t tax unrealized gains sitting quietly in a brokerage account. It only triggers when you borrow against those gains. The moment you access the economic value, you pay tax as if you’d sold.
The counter-argument is that this would discourage leverage. Ackman addresses this directly: that’s a feature. Encouraging billionaires to take massive margin positions against their own companies creates systemic risk. When Tesla dropped 30% in 2022, Musk faced potential margin calls that could have forced selling into a falling market. The tax code shouldn’t subsidize that behavior.
The political math works too. Wealth taxes poll well but die in Congress and courts. This targets only the people using a specific loophole. It doesn’t touch the doctor who borrowed against her house or the small business owner with a line of credit. It’s narrow, defensible, and hard to frame as class warfare.
One shouldn’t be able to live and spend like a billionaire while paying no tax. If you’re extracting value from appreciation through borrowing, you’re realizing the economic benefit.
The tax code should recognize that.