The Boston-Toronto Rivalry Gets Set For Another Chapter

Phil Kessel is a focal point today of a Boston-Toronto rivalry that spans all four major sports.

Phil Kessel is a focal point today of a Boston-Toronto rivalry that spans all four major sports.

The city of Toronto comes to Boston Wednesday night in more ways than one. The big focus is the Maple Leafs’ arrival to start their NHL playoff series with the Bruins. And the reeling Blue Jays are in Fenway to start a three-game series with the scorching hot Red Sox. These coming few days promise to write another chapter in the long sports history between the cities of Boston and Toronto.

Toronto is the only city to have a team in the same division as Boston in all four major professional sports. I’m giving Toronto credit for the Buffalo Bills in the NFL—with Toronto only being an hour and half over the border and actually hosting a Bills’ home game every year I don’t feel like that’s a reach. And the Leafs, Blue Jays and Raptors are all division rivals of the Bruins, Red Sox and Celtics respectively. So to commemorate this gala week of Boston-Toronto battles, let’s look back at some high points of the municipal rivalry…

It’s the longest-running of the four rivalries and by a lot. Much of the history of this rivalry was authored in the Original Six era of the NHL. The Bruins ran into a Maple Leaf road block in the semi-finals in 1933, 1935-36, 1948-49 and again in 1959. On the positive side, Boston knocked off Toronto to win the Stanley Cup in 1939.

These teams haven’t met in the playoffs since the early 1970s. Boston beat Toronto in five games en route to their Stanley Cup in 1972, and the B’s swept the Leafs in 1974, on a path that would lead to the Finals.

Realignment moved Toronto out of the conference for the better part of two decades, and the Leafs haven’t been relevant the past several years. The biggest connection between the two teams has been a trade.  Toronto can thank Boston for their current leading scorer, Phil Kessel. Of course Boston can thank Toronto back for the draft picks that were used on Tyler Seguin and Dougie Hamilton. Sounds like a deal that worked out pretty well for all concerned.


Roger Clemens' amazing career turnaround after leaving Boston for Toronto has since been called into question.

Roger Clemens’ amazing career turnaround after leaving Boston for Toronto has since been called into question.

Maybe not the longest-running rivalry since Toronto’s baseball team didn’t exist until 1977, but there’s a good amount of lore built up here. These two franchises had their best rivalry in 1990-91, when each season saw them battle to the wire for AL East title.

Boston won the 1990 race, clinching on the penultimate day of the regular season. The clinching win came in Fenway against the Chicago White Sox when Red Sox rightfielder Tom Brunansky made a spectacular sliding catch off a line drive off the bat of Ozzie Guillen to preserve a 3-1 win and prevent the race from going to the final day of the season. One year later, Toronto appeared to have the division sewn up shortly after the All-Star break, but the Red Sox ripped off a torrid hot streak in August and September to make it close, before finally coming up short. In both years, the AL East champ fell to the Oakland A’s in the playoffs.

The days of 1990-91 might have been the best, but the saga of Roger Clemens was surely the most notorious point in the relationship between these two baseball franchises. It was Toronto that Clemens opted to sign with after then-Boston GM Dan Duquette decided Clemens was in serious decline after the 1996 season. It was an entirely defensible decision at the time by Duquette—particularly given that one year later he was able to acquire Pedro Martinez, but when Clemens magically turned his career around and won four more Cy Young Awards (including two in New York), the GM caught a lot of heat. Of course we know now that Roger got some extra medical assistance in pulling off his miraculous revival that started with back-to-back Cy Young Awards in Toronto in 1997-98.


Drew Bledsoe first helped Bill Parcells end a Buffalo dynasty, then the quarterback became a Bill.

Drew Bledsoe first helped Bill Parcells end a Buffalo dynasty, then the quarterback became a Bill.

The then-named Boston Patriots won their first division title in 1963 when they beat Buffalo in a one-game playoff for the AFL’s Eastern Division title. This rivalry has been mostly quiet over the years, with the Pats having stirred up more animosity for the Jets and more of a lore with the Dolphins. But New England-Buffalo has had its moments.

Since the AFL-NFL merger of 1970, the biggest on-field moment has been a 1994 regular season game in Buffalo. Both teams needed to win to keep playoff hopes alive. For the Pats, this was about marking their arrival as a contender under Bill Parcells. For the Bills, it was a proud champion—four straight AFC crowns from 1990-93—making its last stand. New England won easily 41-17 and made the postseason the following week.

Doug Flutie would have perhaps his best year as a pro in 1998 when he took over the Buffalo starting job after an injury and led the team into the playoffs. The man who became a legend while at Boston College and later played three years for the Patriots, made his triumphant return to Foxboro in November of that season. The homecoming was spoiled was the Pats won 25-21 on a late touchdown pass from Drew Bledsoe to Ben Coates.

And speaking of Bledsoe…again, we have a situation where the biggest moment in a rivalry is not on the field, but off of it. After losing his job to Tom Brady, it was Buffalo that Bill Belichick ultimately traded Bledsoe too. The Bills were also the destination for New England’s All-Pro safety Lawyer Milloy two years later. Milloy had gotten into a very public battle with Belichick early in the 2003 season leading ESPN’s Tom Jackson to infamously tell the country “They (the Patriots) hate their coach.” New England only won the Super Bowl, sans Milloy.

If you’ve never felt any animosity for the Raptors or even felt an extra chill down the spine when these two franchise meet, I can’t say I blame you. There’s certainly nothing on the basketball court that’s memorable here and if there’s a noteworthy personnel connection I’m not aware of what it might be. The C’s and Raptors have some work to do.

Boston’s rivalry with Toronto doesn’t get the same kind of media love affair that our battles with New York do. But the Boston-Toronto showdowns cover every sport. New additions to the historical treasure chest will be made this week, especially on the ice.

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