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BLOG #8: “Project North Side”

It’s October 27, 2009. You’re a Cubs fan. You are the laughing stock of baseball, the franchise with the longest championship drought in all of sports, and you ended the season finishing second behind the division rival Cardinals. The two years before, you won back-to-back division titles under new manager Lou Piniella, just to get swept in the playoffs by the Diamondbacks and the Dodgers. The night before, you watched the Phillies play the Yankees in the World Series, half of your attention on the game and the other half dreaming that one day your team eventually makes it there. On the business side of things, the sale of your franchise is all but coming to a close. Back in January, you hoped Dallas Mavericks’ owner Mark Cuban wouldn’t have dropped out of the bidding, but he did, and you are left with the children of billionaire and TD Ameritrade chairman Joe Ricketts.

From left to right: Todd, Pete, Laura, and Tom Ricketts

But not all is lost, you tell yourself. You read an article stating Tom Ricketts “once lived across the street from Wrigley Field and met his wife in the bleachers.” It’s like it was meant to be. “My family and I are Cubs fans,” says Ricketts. “We share the goal of Cubs fans everywhere to win a World Series and build the consistent championship tradition that the fans deserve.” The Ricketts family then finalize a deal to purchase the Chicago Cubs valuing at $845 million; they call it “Project North Side”. It includes 95-percent interest in the Chicago Cubs, Wrigley Field, and the Tribune Company’s approximately 25-percent interest in Comcast SportsNet. You convince yourself things are going to get better, you just have to believe.

Fast forward to 2015 – the Cubs make it to their first NLCS since you know when. Then, in 2016, the Cubs do the unimaginable and go on to win the World Series for the first time in 108 years! The city of Chicago is ecstatic, you are the happiest you’ve ever been, and the Cubs drought is over. It’s the fairytale ending. The end.

Simpler times.

Yeah, it was the end alright. Now that us fans got what we wanted, it was time for the Ricketts to get what they wanted. This sparked a transition to venture off into focusing on the family’s profit margins over anything remotely close to involving baseball.

It’s not the end of the world, however, because you still got to watch your Cubs make the NLCS in 2017 and play competitively the following three seasons. But unlike the Cubs, teams like the Dodgers, made impactful moves every offseason to create “the consistent championship tradition that the fans deserve” – I think that’s how Ricketts phrased it. Don’t believe me? Think I am being an ungrateful fan? Since 2017, the Cubs’ notable signings are:

  • 2017: Brett Anderson, Wade Davis (trade), Jon Jay, Jose Quintana (trade), Koji Uehara
  • 2018: Tyler Chatwood, Steve Cishek, Yu Darvish, Brandon Morrow
  • 2019: Brad Brach, Nicholas Castellanos (trade) Daniel Descalso, Craig Kimbrel*
  • 2020 (current): Jonathan Holder, Austin Romine, Kohl Stewart

Sure, some of those names are legit acquisitions. But, when only one of those names is still on the current roster*, what exactly was the point. Of course I will always be grateful for 2016; I was able to witness something that some fans spent their whole lives waiting for and never had the chance to experience. I draw the line on complacency, however, which is exactly what the Ricketts did in terms of handcuffing Theo Epstein and the rest of the Cubs’ front office from going out and building a better team. And yes, I believe some of the blame goes to the players and coaching staff as well. Underperformance was clearly contagious in that dugout, but after 2016, we never had a team that was built to win it all. And the icing on the cake, after signing Darvish, the spending suddenly disappeared – leaving the last two offseasons being nothing short of disappointing, stingy, and embarrassing.


When I first heard the news about the Yu Darvish trade, I honestly saw the angle the Cubs were trying to take. Clearly the team is not competing for this upcoming season, so it makes sense to sell an older pitcher like Yu and get young prospects in return – they even got a quality arm like Zach Davies. But when you get ZERO of the Padres top ten prospects (and no pitchers) in return, there is clearly an issue. It means you made a trade the front office didn’t want to make, but rather was forced to because of money restraints. Furthermore, the Cubs have had crucial players in the past such as Aroldis Chapman, Nicholas Castellanos, and Wade Davis that they bring in and then decide to move on from. I understand some players are rentals, but when they have the impact that they do when they’re here, why wouldn’t you pay them to stay. But we are talking about a team that clearly made it known to their former MVP that he isn’t worth the money he’s getting so… what do I expect?

Blame: Ricketts – for throwing their money on turning Wrigley into a financial empire for themselves instead of on the team that plays there.


Where do I even begin? Too cheap to pay Jon Lester $2 million. Too cheap to spend any money in the 2021 free agency after shedding north of $45 million in outgoing free agents and $59 million in total from Yu Darvish. Too cheap to pay 100 front office employees – some making less than six figures – so the next best option is laying them off. But, wait a second. Not too cheap to agree to a billion-dollar deal with Turner Sports to broadcast the playoffs? Interesting. Considering this is the same family who, when purchasing the Cubs, tried in every way possible to avoid the taxes involved in the sale, and had Todd Ricketts under fire for a property tax issue, it doesn’t surprise me. I get that this is a business, but good luck trying to get fans like myself to have any sympathy for your “biblical” losses when you are only trying to save yourselves.

Blame: Ricketts – for being exactly the type of owner I despise; glad the well-being of people that work for you mean nothing.


COVID-19 was tough for everyone, baseball teams included. David Kaplan reported the Cubs are in around $1 billion of debt between the team and the Ricketts’ real-estate company. The problem I have with the whole situation is the Ricketts knew the risk of owning a big-market team. When you own the Chicago Cubs, you cannot pretend you own a team like the Pittsburgh Pirates when money gets tight. For a team that increases the prices for fans in every aspect, it is mind-boggling to see the inverse relationship in payroll and the desire to put a winning team on the field. It was strikingly obvious that all this ever was to the Ricketts was a gold mine. Their plan: buy the Cubs, buy all the property around Wrigley, renovate, build a winning team, win, cut back spending on team, and continue to increase prices knowing a loyal fanbase like the Cubs will be willing to keep paying. And the worst part – Ricketts’ lack of spending on the team has led to a transition of Chicago baseball belonging back on the south side. But hey, I know one thing is for sure, the Ricketts’ pockets will be just fine.

Blame: Myself – for believing that billionaires with the prior history like the Ricketts would actually care about the team over their financial situation.

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