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The Ricketts family panel returns to the Cubs Convention

Day two kicked off with a candid conversation with the Cubs ownership group.

Photo by Christian Petersen/Getty Images

Cole Wright hosted a conversation with Tom and Laura Ricketts to kick off Day 2 of the 2023 Cubs Convention. Whoever was booing Tom during the Opening Ceremony must have slept in on Saturday morning, because there was only applause in the sparser crowd as the conversation kicked off at 9 a.m. There was a lot of speculation about whether this panel would return after it was removed from the 2020 convention, but to the Ricketts’ credit it was brought back and included a decent number of questions from fans.

I’ll cover three main buckets of questions in this story: the impressive work Cubs Charities continues to do in Chicago, the continued development of additional revenue streams in and around the ballpark, including the sports book, and fan concerns about if and when Sammy Sosa will ever be welcomed back to Wrigley Field.

Cubs Charities

Both Tom and Laura led with how great it was to be back in-person and how much they enjoyed seeing the faces of fans and new players at the Sheraton. Laura spent a bit of time discussing the impressive work that Cubs Charities has done for sports-based youth development and supporting students across the Chicagoland area. She noted they are hoping to announce a sports-based “Urban Youth Academy” that will be a $100 million project housing programs, a kitchen and a community center for young people. Tom added that when he first got involved with the Cubs the charitable wing was relatively small compared to other teams, which they found unacceptable. Tom noted that they’ve built Cubs Charities to be one of the largest, if not the largest, charitable arm in MLB.

Team spending and revenue

As the conversation moved to Cubs baseball, Cole asked about the state of the 2023 Cubs. Tom said he feels great about the state of the team and that Jed Hoyer had a pretty incredible offseason. He stated that there was never a strategy to rebuild, but there were a lot of things that happened that made that necessary. Specifically, he acknowledged they were unable to get the types of extensions that would have been necessary to keep some of the old core and the trade market wasn’t where they thought it would be. But he sounded a note of optimism stating: “All of the last World Series winners had a top 10 farm system before they won,” and that the Cubs farm system is in a much better spot than it was.

Tom also praised the team chemistry and players who took another step forward. He credited that team environment and farm development for making the team a more attractive destination for free agents like Dansby Swanson. Laura added a vote of confidence for the front office saying Jed makes hard decisions and emphatically stating the family’s support for those decisions. She did a nice job of conveying that those decisions are hard on her and the family as well sharing that “when we traded [Anthony] Rizzo I was in tears, but it was the right thing to do.”

I’m still not sure trading Rizzo was necessary or advisable, but as a fan who was also in tears when that text alert hit my phone, I appreciated the moment of empathy.

Cole shifted the topic to spending and what Jed Hoyer has referred to as “intelligent spending.” Laura once again defended the front office adding (and I’m paraphrasing here): Jed says we can throw money at players but you have to stick to the plan, because just throwing money at players won’t get you where you want to go, even if it would make the fans happy.

(This was a recurring theme throughout the morning, there was a similar conversation during the Front Office panel with Jed Hoyer and Carter Hawkins that I’ll detail in my next piece.)

However, it was hard not to notice that the conversation cautioning fans about throwing money at players was almost immediately followed up by a fan question disapproving of the sports book outside the historic landmark the Cubs call home. Tom responded to the sports book question in two ways. The first was defending the process behind the addition and what he said would be a “very, very cool sports book.” He then added that it was necessary for the team to make additions like that to generate revenues for players, which I found odd since Laura mentioned that throwing money at players wasn’t always part of the plan just a few minutes before.

These weren’t the only revenue stream questions Saturday. Another fan asked about development around the ballpark that made Wrigleyville “less accessible” to the average fan, clarifying his concerns were about expense. Tom mentioned that the McDonald’s is still there, just in a hotel. He also noted that other teams make a lot of revenue by offering amenities that are higher priced options for fans, and added that the Ricketts have tried to balance adding those amenities while not leaving behind fans.

Another fan, Brad Nolan, asked about the Ricketts recent attempt to add a Premier League team to their portfolio and if such an addition would pull money away from the Cubs. Tom explained the family’s interest in Chelsea and reassured fans that it wouldn’t have impacted the Cubs spending at all. The Ricketts were not successful in their Chelsea bid, so this is all hypothetical at the moment, but it’s worth keeping an eye on as the family continues their push to diversify revenue streams while spending on players has declined or remained flat relative to peak seasons.

As an aside, look, I understand that teams have to spend money for talent, and I know this isn’t an all or nothing proposition. But the Chicago Cubs were a major market team that printed money before the Ricketts family renovated the ballpark and the neighborhood with a slew of additional monetary streams. They are also a team whose largest contract ever is still the 2016 signing of Jason Heyward to an 8-year, $184 million deal. It is notable that that deal does not make this list of the longest deals ever signed by any MLB team, nor is it close to making this list of the largest contracts (by AAV, or total value) in MLB history. It’s hard to hear the Ricketts defend the addition of a sports book, more high-priced Wrigley Field experiences, plus the hypothetical addition of a Premier League team for a team that just can’t bring itself to extend fan favorites or pay top tier free agents to come to the North Side of Chicago. This is particularly true in a year where the market has rapidly accelerated away from the “intelligent spending” model this front office and ownership group defends.

Sammy Sosa

At this point the first fan question about bringing Sammy Sosa back resulted in an enthusiastic response from the audience. Tom responded succinctly that there is “no new news on that front.” But he wasn’t going to get off the hook that easily, a few questions later a second fan followed up with his own Sosa inquiry stating “With all due respect, you and your family are not the reason I watch baseball. I watch baseball because of Sammy Sosa” before reiterating that fans would like to see Sosa welcomed back. Tom replied that there are two sides to the Sosa debate and stated “that the Hall of Fame agrees and so do fans [he speaks to] who respect the game.”

The announcement of Ryne Sandberg’s statue in Gallagher Way changed the subject from Sammy’s possible return to Wrigley (although, not before another fan suggested Sosa should get a statue from the crowd).


As a lifelong Cubs fan I was glad the Ricketts made time for fans to ask questions again during Cubs Convention. I think there is pretty clearly some tension between their continued diversification of revenue streams and the relative lack of spending for one of MLB’s premier franchises. Additionally, I honestly think it’s past time for Sosa to rejoin the Cubs fold, although I know there are different opinions there. That said, the team’s ownership should be lauded for taking the time to answer tough questions. I’ve had more than a few White Sox fans on Twitter take to my mentions this weekend to point out Sox Fest was cancelled altogether, so while the answers fans received may have been unsatisfactory at times, I appreciate that we got them at all.