What was the biggest mistake in franchise history? Some would point to a failed contract extension for a player like Carlos Delgado. Perhaps it was the badly mismanaged trades such as the Michael Young for Esteban Loaiza deal at the 2000 deadline. But in reality, what set the Blue Jays back decades isn't a move that was made regarding the roster - it was a move of pure greed and no real foresight by ownership back in the mid 1990's.
That was when the last major realignment happened and at the time, Blue Jays ownership lobbied hard to stay in the AL East with the New York Yankees and the Boston Red Sox in order to make higher revenues at the gate. It was a known fact that those two teams' fan bases travel well to visiting cities. With nine home games against each club every single year, Blue Jays ownership couldn't resist the quick cash grab those nine home dates would bring.
In reality though, playing in the same division against two teams with the deepest pockets in the game backfired for almost twenty years and it wasn't until Rogers took over as owners and started to invest in the team that Toronto has been able to keep pace somewhat with Boston and New York. Now with realignment and expansion potentially on the horizon, the Blue Jays should right a wrong, in order to sustain their current success.
Blue Jays need to avoid realignment mistakes of the past to sustain current success
MLB commissioner Rob Manfred made an appearance on WFAN's The Craig Carton Show where he spoke about the possibility of adding two teams, and as a result, realigning the current division configuration. “I think if you did it, you’d probably be eight (divisions) with four (teams each). I think you would try to keep two-team cities separate. That would be my thinking.”
Rob Manfred tells @CMacWFAN that he would like MLB to expand to 32 teams and that the league could realign along geographical lines in eight divisions of four if that happens: pic.twitter.com/h0Vh4nvmxB
— SNY (@SNYtv) January 8, 2026
That would mean the Yankees and the New York Mets would stay separated, as would the Chicago and L.A. teams. Even though that would seem counterintuitive to his overall goal of trying to limit the travel during the season. Regardless some early reports had the Blue Jays playing in a "North" division, moving them away from the Yankees and the Red Sox.
In this proposal, the Blue Jays would join the Detroit Tigers, Milwaukee Brewers and Minnesota Twins in a brand new division. This should be a realignment dream for Blue Jays fans. Toronto would be the big spenders of this quartet and could conceivably compete year in and year out. They would also reunite with the Tigers, who were Toronto's main rival of the 1980's through to the mid-90's before they were separated with the creation of the AL Central.
The problem with being in a division with the Red Sox and the Yankees for so many years isn't just playing them so many times in head-to-head matchups or the fact that those two teams for years had outspent the Blue Jays in free agency, it's that there was never any reprieve to capitalize on a potential down year.
From 1994 until 2015 the Blue Jays finished higher than third in the division just once, in 2006 when they went 87-75 and were still ten games behind the division leading Yankees, and just one game ahead of the Red Sox. This was also a time where there was only one Wild Card spot available and the Blue Jays still finished eight games behind the Wild Card winners, Detroit.
Despite only being the seventh best team in the AL that year, there were several other seasons when Toronto could have made a stronger playoff push, if they didn't have to play a combined 35+ times against those two juggernauts. Take for instance the 1998 season when the Blue Jays were 88-74. A third place finish in the division, and four games behind the Wild Card winners Boston, however, they were one win behind the AL Central champs Cleveland (89-74) and had the same record as the AL West champs Texas.
In 2000, it was another third place finish for Toronto, with an 83-79 record, but they finished 4.5 games behind the Yankees. Another year where none of the AL East teams even won 90 games, the Blue Jays still had to contend with the team that ended up winning the World Series that year, the Yankees.
This isn't to say that the Twins, Tigers and Brewers wouldn't be formidable opponents, but it would allow the Blue Jays to have a better pathway to the postseason. The Twins have very recently knocked the Blue Jays out of the playoffs in a Wild Card series. The Tigers have been one of the top teams in the league the last two seasons thanks to the emergence of Tarik Skubal. The Brewers have been the cream of the crop in the NL Central and finished with baseball's best record in 2025.
But they aren't powerhouses, they are all teams that go through a cycle of contention, and maybe the Blue Jays wouldn't have to be absolutely perfect and wait 30 years to finally get back to the World Series.
There are no gimmies in this game, but not having to battle the Yankees and the Red Sox on and off the field every single year could be a welcomed change of pace for a franchise that is finally seeing it's window of sustained contention fully opened. If the Blue Jays have the chance to move to a new division they should grab it, so that the next 30+ years could have potentially many more moments of championship contention than the previous three decades.
