He spent the fall in New York, and early in 1899 went to London.
One of the most interesting, certainly the most widely talked of, "sporting events" for which Richard was responsible was the sending of an English district-messenger boy from London to Chicago.

The idea was inspired by my brother's general admiration of the London messenger service and his particular belief in one William Thomas Jaggers, a fourteen-year-old lad whom Richard had frequently employed to carry notes and run errands.

One day, during a casual luncheon conversation at the Savoy with his friend Somers Somerset, Richard said that he believed that if Jaggers were asked to carry a message to New York that he could not only do it but would express no surprise at the commission.

This conversation resulted in the bet described in the following letters.

The boy slipped quietly away from London, but a few days later the bet became public and the newspapers were filled with speculation as to whether Jaggers could beat the mails.