The OP asked me to respond since I had mentioned seeing Keon as a rookie. Obviously, I am of an age to comment on his original question.
I have one problem with the question, however. We left for nine months in a village in France at the height of the pennant race this year. We had some sense of the rising excitement in Toronto and much of the rest of the country but the final weeks and the playoffs themselves were after our departure. The games were in the middle of the night for us, though we did get up a number of times to watch the games on the ESPN simulator. That is a very indirect way of following a game!
I think previous posters have touched on both the similarities and differences between the Jays and the Leafs. I started watching the Leafs in the 1958-59 season. The Leafs had gone through a down period after dominating the league from 1945-51, winning five Cups in seven years and, at that point, having more Cup victories than Montreal. Punch Imlach had taken over the team so a new and more energetic management was in place. A number of young prospects were coming up to or had just joined the big club, most notably Brewer, Keon and Mahovlich. Imlach pulled off one of the most one-sided trades in history, getting Red Kelly for Marc Reaume. Johnny Bower was brought in to play goal after having been buried in the minors for years. There was a tremendous rush of excitement as the Leafs made a near impossible comeback to nip the Rangers for the final playoff spot on the last day of the season.
The Leafs even made the finals that year, but were facing the most dominant team of NHL history, the Richard-Beliveau -Geoffrion etc Habs. Still, there was immense optimism all of a sudden, at least as it seemed to a young boy. It took a while actually to win the Cup, as the Leafs did finally in 1962, They won again in 1963, with one of the two Leafs teams both to finish first overall and win the Cup, and in 1964. Cracks were showing in that last season, however, and Imlach had traded a number of players for aging stars like Andy Bathgate and Don McKinney. Imlach got into a pattern then of trading for veterans on their last legs. The last gasp of that era was the unlikely Cup victory of 1967, with, if I recall correctly, ten regulars 35 years of age or older. By the way, that victory disrupted what might otherwise be remembered as yet another Habs dynasty. If they had defeated the Leafs in 1967, they would have won five Cups in a row yet again. That does bring up an important point re what nearly happened in 1993; many of these years featured great playoff battles with the Habs.
I had followed the Leafs from the doldrums of the 50's to a series of championship seasons. I did something similar with the Jays. I watched them from their inaugural season. They were wretched in those early years but it was fun going to the games anyways, when I was in Toronto. Pat Gillick seemed from the beginning a more than competent GM and it was possible to see the Jays improve as they developed their prospects in the minors, made a number of shrewd trades and careful free agent signings. Not everything worked out - Hello Bill Stoneman! - and it seemed that the Jays were stuck on the almost edge of greatness for a number of seasons before breaking through in 1992 and 93.
The processes of growth and development were similar in both cases. They are similiar also in their lasting effect on me. I can close my eyes to this very day and see George Armstrong laboring down the wing to clinch the 67 Cup with an empty net goal. I can do the same and see Joe Carter leaping with joy around the bases with that 93 home run. "Touch em all, Joe. You'll never hit a bigger home run!" Nor would Tom Cheek ever make a bigger or better call.
For me, with respect to both the 93 Leafs and 2015 Jays, it looked as if the whole wonderful process might repeat itself, as it did with the Leafs of my boyhood and the Jays of my still relatively young adulthood. But both are "not quite" experiences. Close but no cigar, or no champagne.
The two experiences were not the same but were similar. The Leafs had been gradually liberated and brought into modern hockey after the death of Harold Ballard, perhaps the worst owner of a major franchise in the history of sports. With the Jays, it happened all of a sudden. There was a flurry of trades and all of sudden, they looked unbeatable. Another difference is that the 93 Leafs did not affect the whole country the way the '15 Jays did. After all, another Canadian team, Montreal (teeth grinding) actually did win the Cup that year.. That brings up another difference. There is an edge of bitterness about the 93 Leafs' loss that is not there with the Jays. I actually think the Royals were the best team in baseball and I don't feel bitterness about the loss. Maybe if I had still been in the country it would be different, but the truth is, I don't feel bitter. The 93 Leafs Cup run however, headed south after an undeniably blown call at a vital moment. What made it even harder to take for me, with my particular history, was that the loss cost us all what was possibly an all time classic, Leafs-Habs Cup final. Unless the structure of the league changes yet again, we will never see one of those ever again.
Still, I've got over it now and even read Kerry Fraser's column on TSN with pleasure.
The success of the Jays looks as if it may be fleeting. I would be surprised if they Jays are entering another period of sustained excellence. But the Leafs... New management, exciting prospects in the system, after a long stretch of terrible play. Perhaps they call pull off a great trade, as with Red Kelly or Doug Gilmour or a free agent signing, the contemporary equivalent of a great trade. Maybe I've seen this script before. I hope so.