Thomas Jennings was apprenticed to John Watson and rode his first winner on Whinbloom, owned and trained by Watson, in the Mile Selling Stakes at Newmarket on 20 October 1905, scoring by half a length from ‘Skeets’ Martin on Raven’s Flight. The following day’s Sporting Life reported: “Jennings deserves a word of praise for the way he rode and never let off riding until well past the post, having made all.”
The following month the diminutive 16-year-old apprentice achieved his greatest day in the saddle when winning the 1905 Manchester November Handicap on 25/1 shot Ferment. In a finish dominated by outsiders, Ferment won by three lengths from fellow 25/1 chance Imari, the mount of William Saxby. Imari and Saxby had won the Chester Cup together earlier that season.
Young Thomas rode three winners in 1905 from seventeen mounts. He rode five winners in 1906.
After coming with a wet sail to win the Canwick Maiden (Apprentice) Stakes on Sheffield, owned by Leopold de Rothschild and trained by John Watson, on the second day of the new Flat season, 19 March 1907, a newspaper report stated that Sheffield was “admirably handled by little Jennings, who looks like shaping well this season”.
Sadly, however, that was not the case. Thomas had just ten rides that year and never rode another winner, finishing with a tally of nine, highlighted by that victory in the Manchester November Handicap.
Ferment: winner of the 1905 Manchester November Handicap