During the winter of 1881-82 further changes took place in the ownership of the City, whereby Mr. Donald Milloy, who had been in charge of her up to this time, ceased to be her managing agent, and Mr. William Milloy and his mother, Mrs. Duncan Milloy, of Niagara, came into control.
The new management declined to renew the previous arrangement and determined to run on their own and separate account on a new arrangement made with the Canada Southern.
On May 20th, 1882 the City with Mr. William Milloy as captain, opened the season with regular trips—"Leaving Niagara on the arrival of the Canada Southern train 9.45; returning leave Toronto 3 p.m., connecting with Canada Southern at 5.30 p.m. Tickets from D. Milloy, Agent, 8 Front street, East."
On Monday 22nd May, 1882, Chicora resumed the usual trips from Toronto at 7 a.m. and 2 p.m., connecting at Niagara with Canada Southern and at Lewiston with New York Central Railway.—"Tickets from W. R. Callaway, 20 King street, East, and 25 York street, or Barlow Cumberland, 35 Yonge street, and 24 York street."
Mr. Callaway then represented the Credit Valley Railway in Toronto, and on their company being absorbed by the Canadian Pacific Railway as part of a through line from Windsor to Montreal, he became its Western Passenger Agent. His wonderful faculty for attractive advertising and catching phrases had immediate effect in creating the company's passenger business against its older rival, and when the "Soo" road was added to the C.P.R., Mr. Callaway's genius for developing traffic was transferred to Minneapolis, where he achieved similar results. The ticket offices at York street were principally for steerage, and Italian business. Passenger business toward the west was at that time exceedingly active. The Canadian Pacific then under active construction around the north shore of Lake Superior, and to the further west, called for large importations of laboring men, making the beginning of our Italian population. Manitoba and our North-West were attracting much attention and the railways beyond Chicago, not having been merged into large corporations but working independently, were offering large ticket commissions, each acting on its own account.
The contest across the lake now created was not pleasant, there being an introduction of a certain amount of local rivalry which was undesirable. The season was a rough one and towards its close the City grounded on the boulders at the entrance to the Niagara River, and was successfully pulled off, but did not finish out the season. Notices were inserted in the public papers that the City of Toronto "would be rebuilt for next season and that work would commence directly navigation closed." Chicora therefore finished the season alone.
The season of 1883 found the steamers running in the same manner—Chicora under Capt. Harbottle to Niagara and Lewiston: the City, Capt. W. Milloy to Niagara only. The season was an unfruitful one, weather cool and disagreeable.
For sake of notoriety the steamers under the leadership of the City were often sent across the lake on days when they had better have remained in port and saved money. It was this mistaken course which led to close of the competition.
A heavy storm from the east was blowing, toward the end of September. The seas were running heavily on the Island, and even sweeping up on the dock fronts in the harbor, no business offering and weather cold with sheets of rain and sleet at intervals. The City had come across from Niagara but Chicora had not been sent out for the morning trip, nor had we any intention of sending her out for the afternoon.
About 3 o'clock it was noticed that the City appeared to be firing up. I was at the time in charge and had given instruction that if the City went out Chicora was to follow but on no account to pass her. Capt. Harbottle and self were walking up and down the front of Mowat's dock, where the Chicora lay, watching the other steamer which was lying at Milloy's Yonge street dock, from which we had for the third time been ousted at the beginning of the season. "By the Lord," said the captain, "she's moving; I'm off."