Section Two: The Working Years

1873: The Career of Sterling

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Thomas Gaskell Shearman

The “Shearman” in Shearman & Sterling was Thomas Gaskell Shearman, a bearded gent ten years older Sterling who was 33 in 1873. Shearman was born in Birmingham, England, in 1834 and came to New York with his parents at the age of nine. At the age of 13, he left school and began to earn his own living, continuing his studies at home under the supervision of his mother. In 1857 he moved to Brooklyn and two years later was admitted to the practice of law in Kings County. Shearman appears to have been a religious man and was quite active in the Plymouth Church, where, among other activities, he was a trustee and also superintendent of the Sunday school. He generously footed the bill for alterations to the school’s facilities, but disliked others to know of it. He also supported deserving young men in providing them the advantage of the college education that he was denied.

Even before becoming a lawyer, Shearman was engaged as the editor of a legal journal and he was the author of several valuable legal text books, one of which was the first textbook ever written on the legalities of negligence. In 1868, Shearman became a partner of David Dudley Field after he defended Field’s honor to others in the legal profession. Field learned of this he invited Shearman for a visit, out of which the partnership was formed. At this time, Field was also acquainted with Sterling who had worked in his office for a year. One of their first clients was the Erie Railway, for whom they handled all legal business; and the firm was thus successful from the outset.

From August 1867 to May 1868 Sterling worked in the office of D.D. Field & Dudley Field. In May of ‘68, he went to work for James K. Hill in the hopes of getting more courtroom experience, something that Sterling felt he needed to become a successful, well-rounded lawyer. But he was not to get that experience. During that late spring, Sterling was pulled back and forth between the two law firms in negotiations for a partnership. Shearman wanted him, and eventually won out. Sterling became a partner in the then-named firm of Field and Shearman, with an annual guarantee of 5% of the firm’s earnings going forward. Sterling originally worked for Shearman as his assistant. In 1870, Sterling and Mr. and Mrs. Shearman would reside for several years in the same boarding house at 316. W 22nd Street, where his close friendship with fellow boarder, James O. Bloss, would also come to fore.

Because Field departed for Europe in 1873, the firm was dissolved and on an even-partners basis, Sterling and Shearman re-founded the firm that continues as Shearman & Sterling today. The new firm was retained to defend Jay Gould and his associates in more than 100 damage suits growing out of the gold panic of 1869 for which Gould and the others were held responsible. The firm was successful in defending against the charges in every instance.

Shearman’s career-making case was the famous suit of Theodore Tilton against Henry Ward Beecher. Beecher and Shearman had long been fast friends and had worked together in the anti-slavery movement. Shearman & Sterling became the attorneys of record in the case and Beecher entrusted the selection of counsel and the entire conduct of the six-month-long trial to Shearman.

In his later years, Shearman specialized in the management of large estates and trust funds that had been placed in the care of the firm. Shearman was a Republican from the time the party was organized until 1884 when he, Beecher, and members of Shearman’s church supported Grover Cleveland for President. Afterward, Shearman remained a Democrat until 1896 when he opposed the election of William Jennings Bryan and supported the ticket of the Gold Democrats. Although he disapproved of the course of the administration in the Philippines, he expressed the belief that it would be impossible for him to vote for Bryan, and said that he intended to avoid politics entirely during the entire election year.

Shearman became convinced that the doctrine of protectionism was bad and became an advocate for absolute free trade. He also became a convert to the single-tax theory of Henry George and spent a great deal of time lecturing on the subject. He was a close personal friend of George’s, but was critical of George’s speaking abilities. In a time when the public regularly attended lectures as entertainment and enlightenment, oratory skills were extremely important to spread an idea.

At the outbreak of the Boer war, Shearman surprised his associates by his active support of the British. He frequently harangued the Boers and praised the policy of the British in Africa.

Unfortunately, in mid-September of 1900, Shearman was seized with a fatal illness after being in Paris with his wife, Ella, since May. They returned to his Columbia Heights, Brooklyn home, where he was confined to bed. His family physician diagnosed an abscess of the left kidney and he died before the month was out. During an at-home operation (a common medical practice in those days) Shearman seemed to accept the surgery well, but about 6 pm that evening he began to sink rapidly. He lasted a little more than three hours after that. News of Shearman’s death spread through his neighborhood where he had lived for so long. It caused general sorrow, particularly among the members of his church.


James Fisk

One could say that the firm was less than discriminating (no pun intended) when it came to accepting clients. Among the clients Shearman & Sterling represented were Jay Gould and his partner (or as some would say, “accomplice”) James Fisk. The pair were always in legal trouble and represented a good source of income for the firm, so maybe they weren’t such bad clients to take on after all.

Gould is perhaps best remembered for his role in 1869’s Black Friday. He manipulated the price of gold by purchasing millions of dollars worth. Then he persuaded President Grant’s brother-in-law to help him, by ensuring that the government would not stop his attempt at cornering the gold market. When the President discovered what his brother-in-law had done, he was slow to act. So for two days, Gould sold his gold at inflated prices, while appearing to buy. Investors followed his apparent path. The price of gold continued to rise and Gould was getting richer as he was selling it. On Friday, President Grant released five million dollars worth of gold for sale and the prices plummeted. The Stock Exchange closed for a short time to “separate the solvent from the ruined.”


Jay Gould

When Gould died of consumption in 1892, he left more than $75 million to his family, or over $3 billion in today’s money.

However, one must realize that times and ways of practicing law and doing business were much different then, and many saw nothing wrong with the way these men conducted business. Other Shearman & Sterling clients were Stillman’s National City Bank of New York, and John D. Rockefeller’s Standard Oil.

Upon Shearman’s Death in 1900, John Sterling, at 57, became the senior partner of the firm of Shearman & Sterling. Ironically, just five years earlier, Sherman & Sterling had moved offices to 44 Wall Street, the same address where Sterling had clerked in the offices of James K. Hill. Now, his other partners were John A. Garver, a Yale Graduate who was nine years older than Sterling, and James M. Beck who was, of late, the U.S. Assistant Attorney General. .

Sterling’s contribution to the firm was “his common sense and his intuitive judgment in business matters, particularly those presenting problems of finance.” All his life he was nervous about speaking before a court or the public, but he was a lion in the conference room.

Sterling also had his Yale connections and a genius for attracting rich men to him and for advising them well on the problems of their companies. In turn, these friends gave him profitable advice from time to time about investments in the stock market, a practice we know as “insider trading” today. Quite on his own, Sterling made a fortune by developing real estate in Westchester County, New York. He never, under any circumstances, appeared in court; he never joined any bar association or took any interest in the profession’s problems; and he never participated in the activities of his church, any political party, or civic or other public movement. In other words, Sterling had a successful career by always remaining behind the scenes and neutral in every way so as not to alienate any interest, especially those of his clients.

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Although never willing to displease a client, travel over the ocean was one business request at which Sterling drew the line. Though willing and required to travel frequently throughout his career, he did so cheerfully, but it had to be overland travel. Sterling was frequently called upon to travel by train, back and forth between cities and states, in order to supervise the closing of deals and agreements. Despite business and social pressures, Sterling’s phobia of ocean travel remained. In the course of business, managing the affairs of his friend James Stillman after Stillman’s retirement to Europe could have been simplified had Sterling been willing to visit him overseas, but he was not. Telephone calls and cables took the place of overseas visits.

Certainly transatlantic travel had evolved since the 1840’s with the first regular transatlantic steamship service, Cunard’s 63-passenger Britannia. (This was the very steamship that author Charles Dickens once described as looking like a large hearse with windows.) However, we also have the contemporary example of the 1912 sinking of the unsinkable Titanic, and the fact that Sterling’s own firm represented one of the survivors in a lawsuit to recover damages, as a point of fact that Sterling’s fear of oceanic travel was not necessarily unfounded or completely unreasonable given the times.

Here again we find evidence of Sterling’s mania for privacy and control that was to reappear later at 912 Fifth Avenue. He maintained an office for visiting clients, but also a secret, locked alternate work area where he actually did the bulk of his labor. People who read of Sterling’s office rules would ask,“Why did Sterling insist on having his staff telegraph him if they were going to miss a day of work, was it a control issue?”


Sterling (left) in his office at Shearman & Sterling


Sterling Memorial Library, opened in 1930, at Yale University

Of the fourteen pallbearers at Sterling's funeral, twelve were either extremely rich men or heads of huge companies, and only two were lawyers: George L. Ingraham, who at the time was president of the Association, and Francis Lynde Stetson. All of these men were involved in some element of Sterling’s business life. Although he practiced law all his life, these men and many others would have regarded him as more of a businessman than a lawyer. On their website, Sterling’s own firm today refers to him as a “boardroom lawyer.”

After the large bequest to Yale in Sterling’s will, John Garver, his partner, was called upon by Yale to produce a tribute book to better acquaint people with Sterling. He accepted the assignment, producing a small 113-page book. Among the book’s contents were pictures of Sterling, some of which appear in this document, and shots of the Sterling buildings on Yale campus, etchings of others planned but not yet built as of 1929 when the book was published.

One of the things that Sterling must have been most proud of was his association with the Miriam Osborn Home, now called simply “The Osborn.”

Charles J. Osborn, a prominent Wall Street broker, was a client of John Sterling’s, and Miriam Osborn was his surviving widow (shown right). Besides serving as executor of Charles’ will, Sterling took it upon himself to look after the funds left to the widow and greatly increased her financial well-being during her lifetime. Mrs. Osborn had seen times of boom and bust in her husband’s career as a broker and lived in fear that she would be left in need if he died during one of the bust periods of his stock brokerage. To that end, she put aside money from his generous allowance to her and had amassed a respectable sum at the time of her husband’s death.


Miriam Osborn

Her fear of being left without means, no doubt, is where the idea for The Osborn, as a home for destitute ladies, came from. In gratitude to Sterling for his kindness, she left a $100,000 “surprise” bequest to him in her will. Sterling assigned this bequest to the home’s trustees and by the time he died, had multiplied it by five. With investments of his own, he amassed the finances necessary to carry out Mrs. Osborn’s wishes to establish a home for women who found themselves in financial distress in their old age. Some of the details of Sterling’s work in this regard are found in the article giving the details of his will, later in this document. Sterling always found ways to channel more money into The Osborn. For instance, his friends, Lords Mount Stephen and Strathcona, had at one time given him $250,000 for personal services that he had refused to accept as compensation. Instead, he invested the sums conservatively and the proceeds were applied to the construction of additional buildings at The Osborn, as memorials for members of the two Lord’s families. Sterling donated additional securities to fund a building as a memorial to his own mother.

Suffice it to say that Sterling’s interest and involvement in the project remained, even up to, and after, his death. His will was very generous to The Osborn, without taking into account the funds he had already raised on behalf of Mrs. Osborn which she endowed to the home upon her death. When she died, Sterling began in earnest to make sure that the home became a reality. He found a suitable property near his home in the country and began to amass land around that property for a park-like setting. From the start of construction until the day it opened, Sterling worked tirelessly to oversee every aspect of The Osborn’s development. Nearly every working day until he died in 1918, Sterling talked with The Osborn’s superintendent about daily business operations. Although at one time it had even more acreage, the community today enjoys 56 acres of beautifully landscaped buildings and grounds.


George Cortelyou

In April, 1908, the first residents moved into a magnificent neo-Georgian-style residence located on the crest of Theall’s Hill, the highest point in Rye, New York. Sterling’s involvement with the home continued long after his death. Those who worked with him in life carried on his work after his death; most notably, George Cortelyou (right), who would have been eminently qualified to serve as director at the Osborne. A former secretary to President William McKinley, and partner in Sterling’s firm, after McKinley’s assassination Cortelyou continued under President Theodore Roosevelt, where he developed White House protocol. He then went on to serve as U.S. Secretary of Commerce and Labor, Postmaster General, and Secretary of the Treasury, all under Roosevelt.

(Peter Rouse Cortelyou, Sterling’s college friend who was, no doubt, related to George Cortelyou, went on to receive his M.D. from Bellevue Medical School in 1867. He married, had two children, and eventually moved to Marietta, Georgia, for health reasons. When his health returned he stayed on to practice in Georgia, where he later held a number of offices in the state’s medical profession.)

Sterling’s former personal private secretary and an amazing woman in her own right, Helen Adams, also was involved with the home in the roles of Trustee, Treasurer, Executive Superintendent and Secretary of Admissions up until she broke her hip in 1960. She then became a resident of the home for the next seven years until her death.

Over the years, many additions, improvements and renovations have expanded The Osborn beyond the footprint of the original building, always with the goal of maintaining the architectural integrity and beauty of the campus. Today, more than 400 men and women live in the beautiful, spacious Sterling Park independent living apartments and garden homes, in the recently renovated original Osborn building, or in The Osborn Pavilion, the state-of-the-art skilled nursing center.


Entrance hall of the Osborn


"1870, Original New York
Cotton Exchange Building
142 Pearl Street"

An offshoot of Sterling's work for the home was that he continued to acquire tracts of land in Westchester County, near Rye, which became what he called his “farm.” Actually, it was more park than farm; but it grew into a hobby at which Sterling spent his free time on in later life. He also bought up connecting farms and developed the land, sometimes parceling home sites out to close friends. After his death, Yale University, who received this not-insubstantial residue of land among other properties left them by Sterling, profited from his hard work. Like other Sterling land bequests left to the University, Yale eventually broke the land up into smaller parcels and sold it off for development, no doubt realizing much more than Sterling had initially invested.

1865: The Career of Bloss
Considered by his parents to be too young to be sent to the Civil War, James O. Bloss came to New York in 1865 where cotton really was to become “the fabric of his life.” At a time when Sterling was in college working toward his M.A. Degree, Bloss, at 18, was out of Rochester High School and already in New York receiving a “real world” higher education. He clerked first for a cotton firm called Norton, Slaughter and Co., and then began clerking as a cotton broker for Woodward and Stillman, under Charles Stillman, James’ father. James was later to become good friends with John Sterling, through an introduction by Bloss. The year that James Stillman became a partner in his father’s firm, 1875, Bloss departed to enter a partnership in a cotton brokerage with John C. Inches. His office would be at 123 Pearl Street, near the first Cotton Exchange.

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India House today

In 1870, a meeting had been held to establish the New York Cotton Exchange, a professional trade organization of cotton brokers. European accounts and trade in cotton futures were increasing to the point that the brokers felt that there should be rules and regulations for systemizing the business. The Exchange was to acquire, preserve, and provide information connected to the trade. In addition, it was to provide a physical location for the organization (shown above) where the brokers could meet and/or do business. Officers and managers were set forth, along with a Board of Appeals to settle disputes.

Pursuant to the mandate for a physical location, the first Exchange was located in the building shown above at 142 Pearl Street. It soon moved to its second location, (shown right) known today as the “India House,” a club at One Hanover Square. The building was originally the headquarters of the Hanover Bank.

Beginning in 1875, Bloss became a partner participating in two consecutive firms, first, with John C. Inches, and then in 1881, with Archie B. Gwathmey. We also know that Bloss wrote a short essay on economic events of the day for a prestigious journal. He, therefore, must have been considered knowledgeable on matters that involved finance as it relates to commodities and the stock market.


New York Cotton Exchange 1885

Meanwhile, in 1885, the Cotton Exchange moved a short distance from One Hanover Street to a new building located at William and Beaver Streets (shown below). This was to be the building where Bloss spent most of his service with the Exchange.

In 1886, Bloss became a member of the Board of Managers. He served two years as a manager, skipped 1888, and returned to the Board for another year as a manager in 1889.

Bloss’ service with the Exchange was not always smooth and according to a New York Times column, (excerpt shown below, right) he was the victim of internal Exchange politics when he was up for re-election to a second term as Vice President. (Though obviously, the politics were not too “internal” as the story was leaked in The Times.)

No explanation of this group’s reason for opposing Bloss is available. However, the opposition was to no avail: he did serve as Vice President in 1890 and '91, and then went on to be President in 1892 and '93.

By 1887, Bloss would have been living with Sterling at 21 East 47th Street for seven or eight years when he published hisGenealogy of the Bloss Family. There is no mention of Sterling in the Genealogy. It was published from Bloss's office which was still at 123 Pearl Street.

In 1891, contiguous with his service at the Exchange, Bloss partnered with George H. Church in a cotton brokerage under the firm name of J.O. Bloss and Company. After his presidency, nothing is known about whether Bloss continued in any capacity with the Exchange while working at his own firm.


"Mr. Bloss Is Not Popular," The New York Times

The New York Cotton Exchange went on in 1923 to a fourth location (shown below). It remained the first commodity group formed in New York City and one of the largest. Annually until 1958, it published the Cotton Year Book that contained each year’s statistics on the cotton industry. It also created various subsidiaries to trade non-cotton contracts, including the Financial Instruments Exchange (FINEX).

In 1998, the New York Board of Trade became the parent company of the Exchange, located on the 8th Floor at 4 World Trade Center. When the World Trade Center was destroyed on September 11, 2001, it had to relocate to a backup location it had established after the 1993 World Trade Center bombing. Since 2003, the Exchange’s headquarters and trading facility have been located in lower Manhattan in the New York Mercantile Exchange Building.

Bloss retired from J. O. Bloss and Company in 1898. According to the constitution of the Exchange, since he was no longer in the industry, he no longer met eligibility requirements to be an Exchange member or officer.

Looking back in later years on his accomplishments, "Who’s Who" was, not surprisingly, short in their entry on Bloss. Bloss “retired” after a career spanning only 33 years, unusual in an age when even wealthy men tended to shun retirement and work till they died. He went on to live out the remaining 23 years of his life with John Sterling until Sterling’s death.


New York Cotton Exchange, 1923

Bloss’ partner in J. O. Bloss & Co., George H. Church, was already working with John Sterling as the Bloss firm’s client, and continued to do so after Bloss’ retirement. In retirement, Bloss continued to serve on various boards and had personal investments, travel, his clubs, his country home, and other activities to fill his time.

1873 Sterling and Bloss Share Residence
Based on what we know about the living arrangements of John Sterling, it is entirely probable that Sterling and Bloss began sharing a residence, outside of boarding houses, at 21 West 25th Street in 1873. However, with what we were able to learn from City Directories and Census reports, the first conclusive evidence of where and when they first shared residence was at 29 W 36th Street, in 1879. If this did take place 1873, this was a good 28 years before they moved to 912 Fifth.

According to Jonathan Ned Katz, in his entry on Sterling and Bloss: "At the end of the 19th century, the failure to marry was becoming an issue of increasing concern. Not marrying was becoming a newly suspect sign of gender impropriety. An earlier commentary about [two unmarried women living together] written about 1860 makes no attempt to explain their not marrying” because it was not considered improper. On the men's side of the gender line, the fast growth of the bachelor apartment house was a widely discussed phenomenon. There were large numbers of unmarried men in New York at the turn of the century, seeking their fortune or furthering their careers.

1874: Sterling Obtains his M.A. Degree
Sterling's father being a man of means and having bequeathed his son $17,000 at the time of his death, Sterling could afford not only the four-year undergraduate course at Yale, but post-graduate education as well.

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J.O. Bloss' country home in Rye, N.Y. (now Harrison, N.Y.) in 1917