“There is no way to sugarcoat it — this is not where we planned to finish the season.”
“This wasn’t the way we wanted the season to end and every year we miss the playoffs is a difficult one.”
“This past season ended too soon.”
“In our 12 years together, never have we experienced so many ups and downs in one season.”
“In a season full of ups and downs, we are grateful for your incredible, ongoing support.”
“While we fell short of our ultimate goal in 2018, our team earned 95 wins for the third time in the past four seasons.”
If those sentences sound familiar, you must be a Cubs fan. Those are the ledes of Cubs chairman Tom Ricketts’ season-ending letters over the last six full seasons (not including 2020), in descending order. Technically, for the 2018 version, that was the lede of his second paragraph, but you get the gist.
Ricketts sent the 2024 edition out last Friday, as the playoffs went on again without the Cubs. No one seemed too enthused. (The Cubs’ own X account didn’t even mention it.)
Hello #Cubs Fans. A song parody inspired by Tom Ricketts letter. pic.twitter.com/9c0g6Hub3C
— Danny Rockett (@SonRanto) October 11, 2024
While every Cubs season these days ends in disappointment, for Ricketts, there is always optimism just beyond the horizon because there is a foundation to build on. And you know what they say about Chicago, there are two seasons: winter and construction. Unfortunately for Cubs fans, “playoff season” is off the table.
We know Ricketts was obsessed with renovating Wrigleyville, and from the boutique hotel to the sportsbook, he’s largely succeeded. Unfortunately, the actual product, the baseball, has stagnated.
With his real-estate focus in mind, along with his interest in buying time, Ricketts often uses variations of the word “build” in these messages. (Thanks to several Cubs websites like CubsHQ.com and Bleed Cubbie Blue for posting old letters.) It’s an easy thing to promise because construction can go on for years and years.
“Our baseball operations staff is redoubling its efforts to build a team that consistently plays in the postseason and delivers the promise of sustained success to Cubs fans. Though we fell short this season, we have strong foundations to build on.”
“That said, we took a major step forward in 2023 and look to build on it for next season. … As an organization, we need to build on our progress and become a team that can finish the race.”
“To win the World Series again we need to build a team that can consistently make the playoffs. … There is positive momentum in our organization. Jed Hoyer and his team are building an expansive core of young high-ceiling players while making investments in infrastructure and technology to help them reach their maximum potential. … As Jed has demonstrated, we will be driven by intelligent decision-making as we build a roster that can win games in the postseason – year in and year out.”
“While we failed to extend our six-straight winning seasons streak and secure our spot in the postseason, we made important changes that put us in a position to succeed as we build the next great Cubs team.”
“Falling short of our potential and failing to make the postseason for the first time in five years was extremely disappointing for all of us. We share your desire for change and are committed to building our next championship team.”
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While he delivered on his early promises of a World Series, the “next championship team” remains an elusive goal for the organization. The Cubs have gone five full seasons (again, not counting 2020) without a postseason appearance. The last two years, they’ve won 83 games, with boring and irrelevant teams.
They spend money but not like most of the other teams in major markets. Since Ricketts has zero appetite to allow his president Jed Hoyer to bid big on players like Bryce Harper, Shohei Ohtani and Juan Soto, the Cubs just aren’t going to bully their way to another World Series. They have to slow-build their way to sustained success, just like they did the last time. (Ricketts loves touting the farm system and those meaningless rankings.)
This year, Ricketts wrote the line about “redoubling efforts” to make the Cubs “a perennial playoff team.”
Last year, he noted: “Over the long term, the key to winning championships is consistently competing for a place in the postseason.”
In 2022, he penned: “As Jed has demonstrated, we will be driven by intelligent decision-making as we build a roster that can win games in the postseason — year in and year out.”
So how has that worked out?
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You’d like Ricketts to come out swinging and offer some promises or challenges, but that’s just not who he is. Even when he hints at paying for progress, he doesn’t follow through, like in 2018 when he wrote:
“Unfortunately, a thrilling summer at Wrigley Field gave way to a disappointing October. Falling one game short in the NL Central and making an early postseason exit, while both unfamiliar and uncomfortable, will motivate us. We will spend the winter working hard to give Joe Maddon and our team the support they need to reclaim our division.”
What did they do? They hired some new coaches, signed Daniel Descalso and Kendall Graveman, and traded Drew Smyly to free up the money to pick up Cole Hamels’ option. And they missed the playoffs, starting this long drought. The 2018 season was the one that worried everyone, inside and outside of the organization.
“Despite our abrupt ending on the field, our team is in no way defined by one Wild Card loss,” Ricketts wrote after 2018. “The overwhelming sentiment, from our front office to the clubhouse, is that we have a lot of work to do and will be back stronger than ever. The talented core that fueled this unprecedented run of success is still in place. Our players are young and hungry. Our fans are committed like no other fan base. We are ready to write the next chapter of our amazing story.”
Six years later, we’re still waiting for the next chapter of the Cubs’ “amazing story,” while Ricketts is trying to manifest the Cubs’ return to the playoffs through his words.
“Now,” he wrote this year, “it is time for us to get to work to bring championship caliber baseball back to Wrigley Field.”
I’d say it’s past that time. But what do I know? I’m just a writer too.
(Photo: Quinn Harris / Getty Images)
