In 1914, the city leaders of the day seriously looked at the possibility of extending the Wentworth Street mountain incline tracks to a point far enough north to eliminate the heavy climb. Their plan was to have the incline tracks pass under the Toronto, Hamilton and Buffalo Railway (T.H. & B.) tracks and over the Grand Trunk Railway (GTR) tracks on a level crossing. That never came about. City businessman George Webb offered to finance the whole scheme himself on the condition that the city of Hamilton undertook construction a permanent roadway on Wentworth Street. In 1915, George Webb had to defend himself when the public asked 'why the Wentworth Street incline costs more to use compared to the James Street incline?' At the time it was costing 15 cents per one hundred school kids on the James Street incline compared to 50 cents per one hundred school kids on his Wentworth Street incline. His defence was that school kids could use his incline on Wentworth any time of the day whereas on the James Street incline school kids were only allowed to be carried on school days between the morning hours of 8 to 9 and the afternoon hours of 12 noon to 2 and 4 to 5.