Englander’s Gamble: The S&P 500 & Century of Certainty

The stock exchange, you see, is a peculiar beast. It devours data like a glutton at a buffet, yet manages to miss the truly significant morsels. The recent filing of Form 13Fs with the Securities and Exchange Commission – a ritualistic offering of holdings, really – is a prime example. It’s a bit like meticulously cataloging the buttons on a coat while ignoring the fact that the fellow is walking about in his undergarments.

Among the titans of Wall Street submitting these documents, one name stands out: Israel Englander of Millennium Management. Overseeing a kingdom of nearly $238 billion (including the somewhat ethereal realm of options contracts), Englander isn’t merely shuffling papers; he’s conducting a grand experiment in capital allocation. And, it appears, he’s placed a rather substantial wager on the American economic engine.

Millennium’s 13F reveals a portfolio of nearly 6,000 positions, a dizzying array of hedges and speculations. But beneath the surface of this complex arrangement lies a surprisingly simple truth. Englander’s largest holding isn’t some exotic derivative or obscure venture capital play. It’s a decidedly old-fashioned investment – a bet on the long-term growth of the U.S. economy. A remarkably straightforward proposition, wouldn’t you say, for a man of such renown?

A History of Profits: The S&P 500’s Unblemished Record

Among the thousands of assets under Englander’s watchful eye, one reigns supreme by market value: the iShares Core S&P 500 ETF (IVV 0.11%). At the close of December, Millennium held 14,494,278 shares – a considerable pile of certificates, representing 4.2% of invested assets, or roughly $9.93 billion. Since June 30, 2025, this position has swelled by a rather impressive 131% (8,212,515 shares). A man knows where to put his money, it seems.

The iShares Core S&P 500 ETF is, in essence, a mirror reflecting the performance of the benchmark S&P 500 (^GSPC 0.08%). Instead of painstakingly assembling a portfolio of 503 individual companies, investors can achieve broad market exposure with a single transaction. It’s a bit like ordering a pre-fabricated mansion instead of laying each brick yourself – convenient, if lacking a certain…character.

The beauty of these equity-tracking indexes lies in their simplicity and low cost. The iShares Core S&P 500 ETF boasts an ultra-low net expense ratio of 0.03% – a mere $0.30 for every $1,000 invested. A pittance, really, considering the potential rewards. Though one suspects the fund managers still manage to enjoy a rather comfortable existence.

But it’s the S&P 500’s historical performance that truly sets this tracking ETF apart. Analysts at Crestmont Research have meticulously examined rolling 20-year total returns, stretching back to the dawn of the 20th century. Even though the S&P 500 wasn’t formally established until 1923, researchers were able to reconstruct the performance of its constituent companies back to 1900. This provided Crestmont with a remarkable 107 rolling 20-year periods to analyze. A truly exhaustive undertaking, worthy of a dedicated bureaucrat.

The findings were, shall we say, rather conclusive. All 107 rolling 20-year periods generated a positive annualized return. Imagine, if you will, an investor purchasing an S&P 500-tracking index (had such a thing existed before 1993) and holding it for two decades. They would have made money every single time. Wars, pandemics, recessions – none could derail the relentless march of progress. It’s a comforting thought, isn’t it? Though it does rather diminish the thrill of speculation.

Englander’s No. 1 holding, therefore, isn’t just an investment; it’s a wager on over a century of historical data. A rather sensible wager, all things considered. Perhaps a bit… predictable. But then again, the most successful schemes are often the simplest. And in the grand bazaar of Wall Street, simplicity is a rare and valuable commodity indeed.

2026-03-12 12:13

A History of Profits: The S&P 500’s Unblemished Record

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