The year 1927 proved to be a dramatic one for the hotel’s second owner, Mr. Bernham Hines. Starting with the sudden death of his wife Helen, aged 26, who was discovered to have died of natural causes while in her private apartment at the Hotel Mossop, it was only a matter of months before the hotel would cease operations. By the end of 1927, the property had been purchased, for a third time, by the Elliott Brothers, local businessmen who would go on to remake the establishment. Reborn as the “Hotel Victoria”, its new name conjuring up images of royal splendour and a bygone era, the hotel entered into its middle years with a renewed purpose. To this end, the hotel, and its revolving door of patrons, evolved with the times. In 1935, nearly twenty years after prohibition had forced the original Hotel Mossop and many other establishments to either change or perish, a notice in The Globe reported that new Hotel Victoria, along with fifteen others like it, had had their liquor licenses restored. Citing the financial difficulties faced by the effected establishments, several of which had since closed, it was stated that the recent reversal on behalf of the Provincial Government had been conducted only after “careful review”. With the taps flowing once again, the Hotel Victoria was once more able to attract the patronage of its target customers – the business travellers and the local 9-to-5 crowd of bankers, broker, lawyers, and others who daily plied their trade in the city.

Following the Great Depression, through the Second World War, and into the 1950s and 60s, the Hotel Victoria would remain a haunt for businessmen – and increasingly – for veterans. Having established the Churchill Club during the war as a fundraising measure, the Hotel Victoria solidified its reputation as a place to swap war stories – of both the commerce and battlefield variety – for a crowd which came to be known over the years as a den of old soldiers and cigar-chomping, Bay Street prospectors. A sign of the times, the hotel’s original, wrought-iron, glass canopy was brought down in 1950, following a years-long spat with the City over monies owed in relation to its upkeep, its vestigial metal support anchors remaining to this day. Then from 1949-1954, during the half-decade of construction for the Yonge Subway, the hotel, as did countless other businesses up and down the city’s main thoroughfare, was forced to endure the inconvenience and disruption related to projects of this scale.