Photo: AP

In the nine years since Monopoly-man-come-to-life Joe Ricketts and his cartoonishly wealthy progeny purchased the Chicago Cubs from the Tribune Company, the Ricketts dynasty—publicly represented by 55-year-old investment banker and public transit enthusiast Tom—have found themselves in repeated disagreement with the Chicago political establishment.

Though Tom Ricketts tends to (wisely) keep his political opinions under wraps, and the family does contain a sole Democratic activist in daughter Laura Ricketts, the remaining Cubs owners are deeply involved conservative players. This presents a problem when, say, a racist anti-Obama ad funded by a Ricketts-founded PAC leaks and the mayor is so furious he refuses to return your calls.

Back in 2013, when the Ricketts had not yet broken ground on their renovations to Wrigley, these disagreements appeared to have inspired at least some of the family to, according to emails acquired by Splinter, consider abandoning the project—or moving the Cubs to a friendlier location, possibly in the suburbs, where the liberal mayor wouldn’t be so dismissive of all the hard work and capital the billionaires poured in to the field as a favor.

In the few years after the Ricketts Family Trust purchased the Cubs, they repeatedly sought to use taxpayer money and subsidies to fund the development of Wrigley and its surrounding areas: They proposed using $200 million of public funds to develop the Triangle Building near Wrigley Field, sought the use of local amusement tax funds that might otherwise be spent on public services, and attempted to use a hefty federal subsidy to pay for renovations of the field. Though the negotiations, Chicago mayor Rahm Emanuel remained unimpressed: “I will not put my money in their field so they can take their money, and invest around the field, and get a greater economic value,” the mayor told ABC towards the end of negotiations, in 2012. “If it’s important, they should invest there.”

The angst over Emanuel’s public position apparently lasted even after the Ricketts family offered to put $300 million of their own money into the field, as well as an additional $200 million into surrounding businesses. Having received a final proposal for the Ricketts investment in the Cubs, Emanuel told the Chicago Tribune:

When I first started this discussion, the Cubs wanted $200 million in taxpayer dollars. I said no. Then they said we’d like $150 million, and I said no. Then they asked whether they could have $100 million in taxpayer subsidies, and I said no. Then they asked about $55 million in taxpayer subsidies. I said no. The good news is, after 15 months they heard the word ‘No.’”

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Todd Ricketts, a prominent Republican fundraiser and the current finance chariman of the Republican National committee, forwarded the story to his father and siblings, writing:

I think we should contemplate moving, or at least recognize that we are maybe not the right organization to own the Cubs.

In a later email, he added:

I just hate the thought of Tom having to grovel to this guy to put money into a building we already own.

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Patriarch Joe Ricketts, a prominent conservative, replied:

Yes Todd, it makes me sad, it hurts my feelings to see Tom treated this way. He is way superior to the Mayor in every way.

I have been brought up to deplore the type of value system adopted by the Mayor of Chicago. This is stating it mildly.

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Though Tom Ricketts is the chairman and public face of the trust that purchased the Cubs, ownership is split between Joe Ricketts’s children, including Todd. The Ricketts sons did not responded to a request for comment on these emails.

Ultimately, no tax dollars were spent on upgrading Wrigley Field, and the Ricketts grudgingly paid for the $575 million, five-year renovations that will conclude this winter. Meanwhile, the relationship between the mayor and the Ricketts family does appear to have improved since the Cubs won a World Series. Still, it remains rather awkward when the family that owns a major baseball team in a liberal city spends more than half a million dollars to air pro–Brett Kavanaugh ads.