She Started as a Secretary at a Wall Street Law Firm in 1947 and Stayed 67 Years. Whenever Her Boss Bought a Stock, She Quietly Bought a Little of It for Herself. When Sylvia Bloom Died at 96, She Left More Than $9 Million.

In February 1947, a young woman from Brooklyn named Sylvia Bloom took the subway to a Wall Street law firm that had opened the year before and started work as a secretary. She was the third person the firm hired. The firm was Cleary Gottlieb, and she stayed 67 years, until she retired at 96. She died in 2016, also at 96, and only then did her family learn what she had been doing with her paycheck. Spread across three brokerage houses and 11 banks, in her own name, was more than $9 million.

The job explains the fortune. In her early decades, a secretary at a firm like that ran her boss’s life, and that included his personal investments. "So when the boss would buy a stock, she would make the purchase for him, and then buy the same stock for herself, but in a smaller amount because she was on a secretary’s salary," her niece Jane Lockshin told The New York Times, which told her story in May 2018. She kept the shares, and she kept quiet. Lockshin thinks it is very possible that Sylvia’s husband, Raymond Margolies, a city firefighter who later taught school and worked as a pharmacist on the side, never knew what she was worth. He died in 2002. They had no children.

Nothing in her life gave it away. She and Raymond lived for decades in a rent-controlled apartment. She rode the subway every day. On September 11, 2001, at 84, she walked across the Brooklyn Bridge and took a bus home. Just before she retired, Paul Hyams, the firm’s human resources executive, saw her coming out of the subway in a snowstorm at 96 and asked what she was doing there. "Why, where should I be?" she said.

Her will left some money to relatives and friends and the bulk, $8.2 million, to scholarships for students who could not pay for college. Henry Street Settlement, where Lockshin was the longtime treasurer of the board, received $6.24 million, the largest single gift from an individual in its 125 years, to endow the Bloom-Margolies Scholarship Fund in its college success program. About $2 million more was split between Hunter College, where she had earned her degree at night while working days, and a second scholarship fund. Nine dollars in every ten she had went to strangers.

Her fortune reads as proof that the plainest habit in investing, buying good companies a little at a time for decades and never selling, beats almost everything cleverer. The limit of that reading is that she had 67 years, a rent-controlled apartment and a paycheck that meant she never had to sell a share at a bad moment; the stocks did the work because she could leave them alone. No published account names the companies she owned, or suggests anyone did anything wrong.

What the Arithmetic Says She Did

The S&P 500, with every dividend reinvested, returned 11.2% a year from 1948 through 2015, by Damodaran’s annual series at NYU Stern. To finish 2015 with $9 million, a steady buyer of that index would have needed to put in about $887 a year, or $74 a month, from her first full year at the firm to her last full year alive. That is $60,338 in all, turned into 149 times the money. She owned individual stocks, since there was no index fund to buy until 1976, and her bosses’ picks evidently did at least as well. The number she had to find each month was small. The number of years was the whole story.

$300 a Month, and What 20, 30 and 60 Years Do to It

Now put her habit on a reader who is 67, retired with a wife of 65, collecting $44,000 a year in Social Security and drawing $60,000 from an IRA. Suppose that for 30 years, from 1996 through 2025, you had bought $300 a month of one company you understood, the way she bought what she watched her bosses buy, reinvested the dividends and never sold. Assume the stock only matched the market. The index’s actual record:

• 20 years, 2006 through 2025: $72,000 put in becomes $330,567, at 10.9% a year.
• 30 years, 1996 through 2025: $108,000 put in becomes $720,821, at 10.3% a year.
• 60 years, 1966 through 2025: $216,000 put in becomes $20,814,399, at 10.4% a year.

The third line is Sylvia’s line. Twenty years of $300 a month buys a cushion. Sixty years of it buys a settlement house a scholarship program.

The record also shows what you would have had to sit through. The 30-year path stood at $68,246 at the end of 2007 and $45,587 at the end of 2008, when the index fell 37%, and it was back to $61,946 a year later. She held through 1974, 1987, the dot-com bust and 2008. This week’s slide, with the Nasdaq-100 fund about 9% below its October record, is the kind of stretch she sat through a dozen times.

Never Selling Has a Tax Number Attached

Take the 30-year line as your position today: $720,000 of one stock, with the $108,000 you paid for it as your basis. The gain is $612,000, which means 85 cents of every dollar you sell is taxable.

Sell it all in 2026 and the whole gain lands in one return. Your adjusted gross income goes from $97,400 to $709,400, and federal tax from $5,492 to $113,649, an extra $108,157: $89,260 of long-term capital gains tax, $17,457 of net investment income tax, and the rest because the sale makes more of your Social Security taxable and takes away the senior deduction. The income also puts the two of you in the fourth Medicare surcharge tier for 2028, which adds $10,711 to that year’s Part B premiums. All in, the sale costs $118,868, and you keep $601,132.

Hold it until you die and the arithmetic changes completely. Under Section 1014 of the tax code, the people who inherit the shares take the market value on the day of your death as their basis. If the stock is worth $720,000 that day, their basis is $720,000. The $612,000 gain that took 30 years to build is never taxed as income, and the $108,157 is never paid. That is the rule Sylvia Bloom’s estate used: the gain built over 67 years went to Henry Street and Hunter College untaxed, and a bequest to charity is deductible from the estate in full.

Giving the Stock Instead of the Cash

The same rule has a version for giving while you are alive. Say you are selling $100,000 of the stock this year to raise cash, which carries $85,000 of gain, and you also want to give $25,000 to a charity. Sell $25,000 more and write a check, and the year’s extra federal tax is $9,457. Give $25,000 of the shares instead, and the charity sells them tax free; your extra tax is $5,925, a saving of $3,532. If you itemize, the deduction is the shares’ full market value either way, up to 30% of adjusted gross income for appreciated stock, under IRS Publication 526.

One limit: at your base income, with no other sale that year, a $25,000 slice of the stock carries $21,250 of gain, which sits under the $98,900 line where a couple’s long-term gains are taxed at 0%. Selling it to give cash costs nothing. The share gift pays in the year your gains stack above that line, which is the year you sell a big piece.

The Bottom Line

A secretary who bought what her bosses bought, in smaller amounts, over 67 years, left more than $9 million and gave nine dollars in ten of it away. On the index’s record, her result needed about $74 a month and 68 years. For a 67-year-old with $720,000 of one stock bought at $108,000, selling it all this year costs $118,868, holding it for life passes it to heirs with the gain erased, and giving $25,000 of the shares in a year you are already selling saves $3,532 over giving cash. She did the first part by habit. The second part is a decision.

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