At his death at 59 in 1887, the estate of Cornelius Van Schaack Roosevelt, Jr. was valued at between one and two million dollars, and included his Maplewood country residence as well as investments and property in New York City. He had inherited a fortune from his father, an investor in real estate, importer of plate-glass, founder of Chemical Bank and one of the richest men in New York City.
Like his brother, Theodore, the father of the future President Theodore Roosevelt, who was a well-known philanthropist, Cornelius Jr. was much beloved and recognized for his charitable disposition. A local newspaper said that Cornelius tipped well and was a great friend of the laboring classes. In 1869, he generously purchased the old schoolhouse on the edge of his estate for $2,000 so those funds could be used in building the new unified district school in Maplewood Village. The old schoolhouse was moved and attached to the back of his estate superintendent's house on the corner of Ridgewood Road and Curtiss Place.
His generous nature was also revealed in his Last Will and Testament. Cornelius, who was childless, provided well for ten of his nieces and nephews, leaving the bulk of his estate to them in equal shares. Nephew Teddy Roosevelt, then President, was reported in 1901 to have received a fortune of $100,000 -$150,000, a current value of $2,650,000 - $3,970,000. The Will’s good intentions were challenged by his brother, former Congressman Robert B. Roosevelt, who contested the omission of his children, Emma and Robert B. Jr., but the court found this to be invalid.
In 1901, the court also confirmed that the Will specifically disinherited nephew Cornelius Roosevelt. It is likely Cornelius the uncle did not approve of Cornelius the nephew, who was said to be a hedonist and an expatriate living in France. In 1902, a claim against the Estate was filed by Mrs. Gertrude Motley for $25,000 as a creditor of the disinherited Roosevelt. It was rumored that Mrs. Motley was an adventuress and possibly his mistress.