James Watson Webb II (known as James Sr.) (1884 – March 4, 1960) was an American polo champion. He was a grandson of William Henry Vanderbilt and James Watson Webb.
He was born in 1884 to Eliza Osgood Vanderbilt (1860–1936) of the Vanderbilt family and William Seward Webb in Burlington, Vermont. He married Electra Havemeyer, daughter of Henry Osborne Havemeyer and Louisine Waldron Elder, and had five children:
James II died in 1960.