$55,000 Lake Shore and Michigan Southern Railway Co. signed by James R. Roosevelt, Douglas Robinson and Robert H.M. Ferguson - 1902 dated Stock Transfer and Receipt

$55,000 Stock Transfer and Receipt signed by James R. Roosevelt, Douglas Robinson and Robert H.M. Ferguson. Trustees for Caroline W. Astor successors to Henry B. Ely, James R. Roosevelt and Douglas Robinson Trustees for Caroline W. Astor. Only 1 issued to Caroline. Very Rare!

Caroline Webster "Lina" Schermerhorn Astor (September 22, 1830 – October 30, 1908) born in New York, Caroline Webster “Lina” Schermerhorn Astor hailed from a wealthy family with deep colonial Dutch roots. In 1853, she married William Backhouse Astor Jr., solidifying her prominent position within the esteemed Astor family. Leveraging her elite lineage and formidable personality, she wielded significant influence over New York City’s high society during the Gilded Age. In collaboration with her social partner Ward McAllister, she established “The Four Hundred,” an exclusive social club that epitomized the upper echelons of fashionable society. Their lavish annual balls and stringent invitation protocols served as the ultimate gatekeepers for social advancement and acceptance. Tragically, Lina Schermerhorn Astor passed away on October 30, 1908, leaving behind an enduring legacy as the undisputed queen of American high society.

James Roosevelt Roosevelt (1854-1927) James Roosevelt "Rosy" Roosevelt (April 27, 1854 – May 7, 1927) was an American diplomat and the older half-brother of President Franklin Delano Roosevelt (FDR). He was the son of James Roosevelt I (1828–1900) and his first wife, Rebecca Brien Howland (1831—1876), who were second cousins. Rosey has been described as "an aimless if charming member of New York society's sporting set." He served as Secretary of the United States Legation in Vienna and as Secretary of the Embassy in London. When his father died in 1900, the estate was split between Rosy and FDR. On November 18, 1878, Rosy married Helen Schermerhorn Astor (November 27, 1855 — November 12, 1893), the second daughter of businessman William Backhouse Astor, Jr. (1829–1892) and socialite Caroline Webster "Lina" Schermerhorn (1830–1908). Roosevelt and Helen had two children: James Roosevelt "Tadd" Roosevelt, Jr. (August 20, 1879 – June 7, 1958) Helen Rebecca Roosevelt (September 26, 1881 – July 8, 1962) After Helen's death, Roosevelt married Elizabeth Riley in 1914. She died in 1948. Since he and Franklin had never been particularly close, Franklin found himself surprisingly saddened by Rosy's death.

Douglas Robinson Jr. (January 3, 1855 – September 12, 1918) was a prominent American businessman and real estate broker during the Gilded Age. Born in Edinburgh, Scotland, to a well-connected Scottish-American family, he was the son of Douglas Robinson Sr. and Frances Monroe, a grandniece of U.S. President James Monroe. After spending his childhood in New York, he traveled back to England to graduate from Oxford University. Upon his return to New York, he became a dominant force in the city’s rapidly growing property market. He held the positions of president of both the Douglas Land Company and the Douglas Robinson, Charles S. Brown Company. His influence extended beyond real estate, as he served on the board of directors of major institutions, including the Equitable Life Assurance Company and the Astor Trust Company. His financial acumen was so highly regarded that, after the Panic of 1907, he was appointed as a receiver to oversee the restructuring of New York’s complex Metropolitan Street Railway Company.
Beyond his financial pursuits, Robinson was deeply intertwined with high society through his marriage and esteemed social standing. In 1882, he wed Corinne Roosevelt, the sister of future U.S. President Theodore Roosevelt and the aunt of First Lady Eleanor Roosevelt. This union firmly established him as a central figure in American political and social royalty. His lineage earned him and his family a coveted place in Ward McAllister’s renowned “Four Hundred” index, which meticulously cataloged New York’s most exclusive social elite. The family resided in a townhouse in Manhattan, a sprawling estate named “Overlook” in West Orange, New Jersey, and Gelston Castle, a majestic Scottish-style country home in Jordanville, New York. Robinson passed away in September 1918, leaving behind a legacy as a pivotal player in New York real estate and a prominent fixture of American high society.

Robert Harry Munro Ferguson (1868–1922), a Scottish-born adventurer, military officer, and close personal friend of President Theodore Roosevelt, was born into an illustrious family in Raith, Scotland. As the third son of Colonel Robert Munro Ferguson MP, he faced the challenge of carving out his own path due to limited family inheritance. Ferguson embarked on a journey across the Atlantic as a young adult. Initially, he served as the aide-de-camp to Lord Aberdeen, the Governor General of Canada. In 1895, he relocated to New York City, where his charismatic personality quickly propelled him into the elite social circles.

In New York, Ferguson secured employment at Douglas Robinson’s real estate firm and worked as a secretary for Colonel John Jacob Astor. However, his true calling lay in the military. When the Spanish-American War erupted in 1898, Ferguson eagerly volunteered alongside Roosevelt. He distinguished himself in Cuba as part of the legendary Rough Riders cavalry regiment.

Through his close ties with the Roosevelt family, Ferguson met Isabella Dinsmore Selmes, a captivating young socialite and Eleanor Roosevelt’s confidante. Despite an eighteen-year age difference, they wed in July 1905 at Oyster Bay, with their wedding being a grand affair attended by their influential political acquaintances. The early years of their marriage were filled with joy, and they welcomed two children, Martha and Robert. However, their idyllic life was abruptly disrupted in 1908 when Ferguson was diagnosed with tuberculosis. Seeking a drier climate to alleviate the disease, the family relocated from a sanitarium in the Adirondacks to a remote ranch near Tyrone, New Mexico. Ferguson bravely fought the illness for the rest of his life, managing his ranch and hosting visits from his lifelong friend, Theodore Roosevelt. Tragically, he succumbed to the disease on October 3, 1922, in Santa Barbara, California. After his passing, Isabella, his widow, achieved historical significance as Arizona’s first congresswoman.

The Lake Shore and Michigan Southern Railway (LS&MS) played a pivotal role in shaping America’s transportation landscape during the 19th century. It connected Buffalo, New York, to Chicago, Illinois, forming a crucial link in the nation’s expanding rail network. Established in 1869 through the consolidation of several smaller lines, including the Michigan Southern & Northern Indiana Railroad and the Cleveland, Painesville & Ashtabula Railroad, the LS&MS embarked on a mission to create a fast and efficient route along the southern shore of Lake Erie. This strategic path, renowned as the “Water Level Route” due to its flat terrain, circumvented the steep mountain grades of competing lines, making it an ideal choice for transporting goods.

The LS&MS’s rapid growth transformed it into a formidable industrial powerhouse. It facilitated the swift movement of Midwestern agricultural products to Eastern markets, significantly contributing to the expansion of major manufacturing hubs such as Cleveland, Toledo, and South Bend. Recognizing the immense strategic and economic value of the LS&MS, transportation magnate Cornelius Vanderbilt acquired a controlling interest in the railway. This acquisition led to the standardization of its operations, aligning them with Vanderbilt’s expanding rail empire. By the late 19th century, the LS&MS had become an integral and highly profitable arm of the New York Central (NYC) system. It even hosted the legendary 20th Century Limited passenger train on its fast Midwestern tracks.

In 1914, Vanderbilt’s interests formally merged the LS&MS with the New York Central & Hudson River Railroad, officially forming the modern New York Central Railroad. Today, much of the historic LS&MS mainline continues to thrive as a vital commercial artery, operated by Norfolk Southern Railway.

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