James Roosevelt "Tadd" Roosevelt, Jr., (August 20, 1879 – June 7, 1958) was an American automobile worker. He and his sister Helen Rebecca Roosevelt (1881–1962) were the children of diplomat James Roosevelt "Rosey" Roosevelt (1854–1927) of the Roosevelt family and Helen Schermerhorn Astor (1855–1893) of the Astor family.
Tadd's uncles were President Franklin Delano Roosevelt (1882–1945) and Colonel John Jacob "Jack" Astor IV (1864–1912), but nonetheless was three years older than Franklin. Tadd's paternal grandparents were businessman James Roosevelt I (1828–1900) and Rebecca Brien Howland (1831–1876) while his maternal grandparents were businessman William Backhouse Astor, Jr. (1829–1892) and socialite Caroline Webster "Lina" Schermerhorn (1830–1908).
Upon his mother's death in November 1893, Tadd inherited $1,500,000 (equivalent to approximately $39,372,222 in 2014 dollars). He and Franklin both attended Groton School and Harvard University, with Tadd being ahead of Franklin. Their kinship led to Franklin often being mockingly referred to as "Uncle Frank" while the two attended Groton together.
After Tadd dropped out from Harvard, he married Hungarian-born prostitute Sadie Messinger (c. 1880–1940) on June 14, 1900. Tadd's father Rosey, upon learning of the wedding, came down from Hyde Park and brought Tadd home. Their union sparked controversy, and Rosey ended up disowning Tadd. Grandmother Lina and Grandfather James also highly disapproved of his marriage to Sadie.
In February 1917, Tadd was arrested in Florida and required to stay in Florida pending a divorce suit. He had lived in Daytona under the name "M. S. King" with a different woman than Sadie. The Roosevelt family had reportedly opposed the marriage to Sadie and had prevailed in achieving a separation, in which Sadie was to receive a $10,000 (equivalent to approximately $184,078 in 2014 dollars) annual income. A court soon granted $625 (equivalent to approximately $11,505 in 2014 dollars) per month alimony to Sadie, pending settlement of the divorce. At the time, Tadd was reported to be the Floridian paying the highest income taxes, having a $12,000,000 wealth (equivalent to approximately $220,893,506 in 2014 dollars).
By October 1921, Tadd and Sadie were reportedly no longer living together. However, they remained married until her death. He died childless and left his money to the Salvation Army.
- "Boy Millionaire Weds; James R. Roosevelt, Jr.'s, Step Without His Father's Consent". New York Times. October 19, 1900.
- "J.R. Roosevelt Arrested; Put Under $50,000 Bond to Stay in Florida Pending Divorce Suit". New York Times. February 24, 1917.
- "J.R. Roosevelt Must Pay; Court Grants $625 a Month to Wife Pending Settlement of Suit". New York Times. March 3, 1917.
- "Mrs. J.R. Roosevelt Jr. Accused of Slander; Mrs. Schultz of Lynbrook, L.I., Itemizes Four Occasions and Sues for $40,000". New York Times. October 1, 1921.
- FDR Genealogy
- Moffat, R. Burnham The Barclays of New york: who they are and who they are not,-and some other Barclays (1904)
- Sadie Messinger
- Tadd Roosevelt
- Black, Conrad Franklin Delano Roosevelt: Champion of Freedom (2005)
- Panchyk, Richard Franklin Delano Roosevelt for Kids: His Life and Times with 21 Activities (2007)