“Imagine a world where you aren’t a Boston sports fan” is a commonly used phrase among the people in the state of Massachusetts, and rightfully so. Boston sports have been on an unprecedented run throughout this entire millennium, thus spoiling the fans with more parade days than Ben Affleck haters. 12 championships in 17 years is pretty wild to imagine. It takes a combination of timing, luck, and having the greatest Head Coach and Quarterback in NFL history (and stealthy camera crew) to put together such a run.

Seeing this latest championship got me to thinking though, are the Chicago sports teams set up to embark on a similar run of dominance across the board? Can we put together 12 rings in 17 years? I will start the tally with the Blackhawks Stanley Cup in 2010, so as of now Chicago has 4 (3 Blackhawks, 1 Cubs) and need 8 more by 2027. Let’s take a deeper dive into each team individually and you can decide for yourself. Disclaimer: I will be doing this analysis through the lens of a realistically optimistic fan.

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Super Bowl Super Bears! This team has all the momentum in the world going into next season. After years of being a lower tier team in the league, it seems like the pieces are falling into place.

I can sit here and talk about how we have the defense, which we do (and as we just saw defense indeed still wins championships). I can talk about how we have bolstered our offensive line, and have skill players that don’t suck. But in a league that is so hard to have sustained success, you have to look at the core infrastructure of an organization: The GM, Head Coach, and Quarterback. Ryan Pace has shown that he is an elite GM and knows how to build a roster, doing so in New Orleans and now in Chicago. Pulling the trigger on a generational talent like Khalil Mack, and building a team through the draft, these are things that feed into sustained success. Now all he needs to do is find a competent kicker and we are sitting pretty.

Matt Nagy coming in as the head coach brought a spark and new identity to the offense. He is the epitome of the new age coach as he not only has a system in place X’s and O’s wise, but more importantly has brought culture to the locker room that the players love to be around. Club Dub is the epitome of what is being built in Chicago that will pay dividends in having players across the league wanting to sign with Chicago.

Mitchell Effin Trubisky, 10 God. A lot riding on this man’s shoulders, and there are a multitude of different opinions on the man, but I believe he will continue to develop and be as good as needed to bring home a Lombardi Trophy for the Bears.

Titles By 2027: 3

Bears celebrate win over Rams at Club Dub

Swag 🏄‍♂️ at #ClubDub!

Posted by Chicago Bears on Monday, December 10, 2018


There is no waiting or anticipation, the time was and continues to be now for this organization. Through building up their farm system and having players like Javier Baez, Kris Bryant and Kyle Schwarber pan out, this team is still very much dangerous.

It certainly does not hurt that the boy wonder Theo Epstein is still at the helm, and you can be sure that he will continue to put the right people in place to win another World Series.

It will only be a matter of keeping as much of the young talent as possible once they are due big time contracts, but once again, we should trust Theo to make the necessary moves to keep the Cubs World Series competitive.

Titles By 2027: 2


Remember when I said I will be doing this analysis through the lens of a realistically optimistic fan? Well, I think it is safe to say that we used up all of our pull with the basketball gods in the 90’s. The only possible way they can even sniff a championship is if the #TankForZion campaign is a success and he turns out to be what everyone expects. Either that or Michael Jordan coming out of retirement for the 7th time.

In essence, fire Gar/Pax, burn the entire organization to the ground and build it through Zion, or strap in for more shitty basketball in the years to come.

Titles By 2027: -1

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Ohhh you bet your sweet ass I’m counting the Chicago Fire! Why should we not be able to count having a professional team for the most popular sport in the world?

“The Chicago Fire won the MLS Cup in their inaugural season in 1998, a feat unmatched by any other expansion team in a major U.S. sports league.” – Wikipedia.

Hell if we start rattling off MLS championships don’t sit there and tell me you won’t celebrate it accordingly. Go get drunk on a Tuesday for parade day and not get judged for one second? Yeah sounds legit to me. I have a feeling that the team is going to catch a fever (get it) and become a force to be reckoned with.

Titles By 2027: 2

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White Sox:

I hope everyone got their laughs in when the Sox fans started saying #2020WorldSeriesChamps. Us South Side folk are all about the law of attraction, you speak things into existence, and they will happen.

The White Sox have taken the blueprint from the team up north and it is playing right on cue. Building the farm system is the first step, having said young stars pan out is the next.

Players like Yoan Moncada and Eloy Jimenez are a pivotal part of the process, along with Michael Kopech once he is back in 2020 for our first World Series run. This has been a long term strategy, and if they land Manny Machado which many suspect (or who really knows at this point), I’m feeling really dangerous if I have on the black and silver.

To end this out with a hot take, I believe we will have a White Sox-Cubs World Series showdown within the next 5 years.

Titles By 2027: 2

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The firing of Coach Q was without question a very bad move by the organization. It was a bad start to what many are seeing as an overhaul for the organization (or just Stan Bowman going through a power trip). The players from our glory years are looking really old i.e Keith, Seabrook, Crawford. However, the Hawks still have two of the best players in the league in Patrick Kane and Jonathan Toews.

I believe the blueprint for them to get just one more by 2027 would be to re-load on young talent, try not to dish out players like Panarin (but ayyy we might get him back) and have Kane and Toews be the savvy veteran leaders. They do that, then we may see Kane doing one last bump off Lord Stanley’s cup just for old times sake.

Titles By 2027: 4

Overall Tally: 3+2-1+2+2+4 = 12

Now it is time for Chicago to gear up and be ready for utter dominance across the board in the coming years. Cue the music!