On the last Sunday in August, the Chicago Cubs hosted the 19th annual “Out at Wrigley,” a community outing at Wrigley Field billed as “the nation’s original gay day” at the ballpark. By all accounts, it was a resounding success.

Members of the Cubs LGBTQ fanbase were tapped to throw out the first pitch and sing the national anthem. A massive gathering of fans showed solidarity by watching the game while seated next to a group of rainbow flags in the left field bleachers. For one day, Wrigley prominently displayed several banners connected to Pride alongside one reading “2016 World Champions.”

On the surface, the only thing that came close to spoiling the day was a Cubs loss, with Nick Castellanos’s would-be walk-off home run dying a few feet in front of those same left field bleachers in the 10th inning. As someone who has followed this team all season, I can verify that the 2019 Cubs have an uncanny ability to instantly transform any game from the opening number of “The Birdcage” into the final shot of “Call Me By Your Name.”

Nick Castellanos doing a spot on impression of “every Cub fan everywhere” on Sunday.

As every Cub fan knows by heart, though, with the exception of that blessed season of 2016, there’s always a “but…” And that proved to be the case even with an event as affirming as “Out at Wrigley.” Because in order to fully embrace the experience at the ballpark, you also had to come to terms with with the conflict inherent in a pro-LGBTQ event hosted by a team owned by the Ricketts family.

As Out Magazine’s Nico Lang pointed out during that same weekend, the Cubs were holding an LGBTQ community celebration at Wrigley Field just a few months after co-owner Todd Ricketts was named finance chairman of the Trump Victory Committee, the Republican National Committee’s political action committee supporting Trump’s 2020 re-election campaign.

This is the Ricketts family’s latest foray into political fundraising, an area that they know quite well.

Federal Election Commission online records show Todd Ricketts has donated a total of $55,600 to both the president’s PAC and his campaign since January. His brother, co-owner and Nebraska Gov. Pete Ricketts (R), is a longtime supporter of GOP candidates who vowed to defend the state’s same-sex marriage ban when running for office in 2015. While Cubs chairman Tom Ricketts publicly plays things down the middle, he supported Trump, the RNC and other Republicans in 2016, as well as a software firm called ActBlue which helps finance Democratic candidates; in January he backed Democrat Bill Daley in his unsuccessful run for Chicago mayor.

In recent months, the Ricketts siblings have gone to great lengths to distance themselves from their GOP mega-donor father, Joe, since the publication of his emails containing racist jokes and conspiracy theories.

And then came news this last June that the Cubs and Ricketts treated a number of Trump Victory Committee donors to a luxury box at a Cubs game during the committee’s meeting in Chicago.

At the same time the Cubs were publicly celebrating their connection to the LGBTQ community, the Trump Administration was filing briefs with the Supreme Court arguing that it should be legal for companies to fire workers specifically because they are gay, lesbian, or trans. This came on the heels of Trump’s Secretary of Education agreeing to investigate a Title IX complaint that could prevent trans athletes from competing according to their gender identity.

And, as Out Magazine noted, that was just that week.

Todd Ricketts on Undercover Boss. Presumably this was not one of the activities on the Trump Victory Committee itinerary.

All of this is not to imply that “Out at Wrigley” itself was anything less than a beautiful day at the ballpark. As founder Bill Gubrud told Outsports, “I sold just as many tickets this year as I did last year. We actually had about 35 to 40 percent of the attendees new to the event.” And that’s legitimately great. As a Cub fan, it’s a point of pride to see the team makes it a priority to maintain a strong connection to the community, as Gubrud further related that co-owner Laura Ricketts visited the gathering in the bleachers for over an hour.

But at the same time, it’s also impossible to put the family’s connection to the Trump administration out of mind when reflecting on the event. Todd Ricketts’s position as finance chairman makes him one of the most prominent figures in the president’s re-election bid. And through his public participation in that campaign, Ricketts is demonstrating his support for four more years of the Trump Administration’s anti-LGBTQ policies and practices, whether or not he publicly agrees with them.

This is not a matter of forcing politics onto an otherwise apolitical celebration. If the Ricketts family wants to be as active as they are in an administration practicing this kind of discrimination, it would be naive of them to expect us to ignore that when they reach out to the community.

To put it in baseball terms, that’s like writing “In Game 6 of the 2003 NLCS, the Cubs were five outs away from a pennant. REDACTED REDACTED REDACTED NOTHING TO SEE HERE. Thirteen years later, they won. The End.”

All of this is a matter of public record. Now the burden falls on myself as a fan to answer a question that was extremely familiar for 108 years: how much are you willing to endure? Only this time, the stakes are much higher.

Having followed this team with a devotion that can only be described as Kathy Bates in Misery-esque, I know how this usually goes. Cub fans like myself will drape ourselves in angst and question why we support a team that gives us so much torment because for most of our lives, it was all we knew. But all it takes is one Javy Báez tag that violates the laws of physics but not baseball and we’re back to all in. For whatever reason, it’s hard to stay mad at the Cubs. Despite them sometimes giving us every reason to do so.

The culture surrounding Cub fandom is one that prioritizes supporting the team through thick and thin. This mentality has been reinforced on the field, as decades of heartache eventually paid off with the greatest World Series of all time. But because this instinct is so ingrained as a fan, it also makes it harder to hold ownership accountable when they do something objectionable.

It’s also difficult because for the most part, the team on the field is still populated by skilled and likable players like Báez, Anthony Rizzo, Willson Contreras, and Kris Bryant. (They also have one extremely terrible person on the team but that’s another article entirely.) Once the game starts, I’m not cheering for the Ricketts, I’m cheering for Ben Zobrist and Jason Heyward.

Furthermore, the team’s outreach to Chicago’s LGBTQ community has been impressive and goes beyond just one successful “Out at Wrigley” event per year. I’ve written before about my admiration for Laura Ricketts’s position as the first out LGBTQ co-owner in baseball history and she remains very active in the community through her work on the National Leadership Council of Lambda Legal and contributions to a number of out congressional and senate candidates like Tammy Baldwin and Sharice Davids.

That’s weird. I wouldn’t have guessed Todd Ricketts was a lefty.

The Cubs are also an annual participant in Chicago’s Pride Parade and in past years, the team has been represented by Hall of Famers Ernie Banks and Ryne Sandberg. Among the current roster, pitching ace Jon Lester has taken it upon himself to interact with members of the LGBTQ community on Twitter in the wake of other players’ homophobic tweets and has come away with a better understanding of where we’re coming from.

All of that adds to my pride in my team. But (there’s that word again) the Cubs can’t stop making it complicated. Last season, in an attempt to fix an offense that broke, the Cubs traded for noted homophobe Daniel Murphy just in time for him to get booed at that year’s “Out at Wrigley”. And off the field, considering Todd and Pete Ricketts’s affiliation with anti-LGBTQ candidates and causes as well as Joe Ricketts’s e-mails, it feels like the majority of Cubs ownership is determined to put my devotion to the test every day. Is there a breaking point? What would that be? And if Todd Ricketts overseeing Trump’s re-election isn’t a breaking point, what does that say about me?

These are hard questions to answer. They hover over my fandom just as they hover over an otherwise joyful event like “Out at Wrigley,” even if the Cubs want to pretend they don’t. It would be great to live in a world where I didn’t have to ponder all of this while cheering for my favorite team in the world. But because of the choices certain members of the Ricketts family have made, that kind of world is just not possible.