I think Jays24 has a point here. Rogers obviously knew the market size, but 2015/2016 were a huge wake-up call in terms of what a winning team actually meant for the city and the country. The atmosphere at the Dome, the TV ratings, the merchandise sales - it showed ownership just how massive the demand was when the team was competitive.
Before that, for most of Rogers’ ownership, the Jays were largely middling and baseball’s popularity in the city had dipped. Those playoff runs reminded everyone, including ownership, what the ceiling of this market really is.