In 2010, TD Ameritrade founder Joe Ricketts bragged about how difficult it had been to purchase the Chicago Cubs.

"That was the most complicated transaction I've ever seen," the billionaire told an entrepreneurship group in Omaha, according to video posted on YouTube and recently unearthed by the Chicago Tribune. "I think there were over 300 documents that were signed."

That transaction - which took place in 2009 and reportedly required selling 34 million shares in TD Ameritrade for roughly $403 million - now poses some new complications for the team, which is formally owned by Ricketts's four children. On Tuesday, Muslim groups called for the team to take a stronger stance against intolerance and bigotry after the outlet Splinter News published this week a trove of racist and Islamophobic emails that Ricketts had sent or shared over the years, which in turn led the Cubs' leadership to distance themselves from him.

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"Being a baseball fan can be heartbreaking in itself if your team doesn't win the last game of the season, and it is heartbreaking to know that the team you have loved ever since you are a kid has sentiments linked to it in the way that was represented by Mr. Ricketts," Kamran Hussain, the president of Chicago's Muslim Community Center, wrote in an open letter on Tuesday.

Ricketts, 77, is a prominent Republican donor who has given millions to conservative candidates and political action committees. In 2015, the campaign finance watchdog group OpenSecrets noted that he had donated so much money to campaigns over the previous year that he single-handedly made Wyoming, where he lives, the top state in the country for per capita contributions. His son Pete Ricketts currently serves as the Republican governor of Nebraska and chairs the Republican Governors Association. Another son, Todd Ricketts, was named the finance chairman for the Trump Victory Committee last week, in advance of the 2020 election.

In the emails published by Splinter, which were sent between 2009 and 2013, Ricketts expressed a deep-seated fear of Muslims. In one 2012 email, he wrote, "Christians and Jews can have a mutual respect for each other to create a civil society. As you know, Islam cannot do that. Therefore we cannot ever let Islam become a large part of our society. Muslims are naturally my (our) enemy due to their deep antagonism and bias against non-Muslims." He added that he was considering "having a book written with the title 'Islam, Religion or Cult,'" which "would describe many things about Islam but most importantly describe and define where Islam crosses the line from religion to a cult."

During that time, Ricketts repeatedly forwarded chain emails containing unfounded conspiracy theories about President Barack Obama to acquaintances. One particularly bizarre message from 2011 suggested that Obama had gone by "Barry Soetoro," using his stepfather's last name, and had worked as a gay prostitute and a drug mule, trafficking heroin from Pakistan to New York, before coming up with the name "Obama" to defraud the Internal Revenue Service. Another, from 2010, posited that Obama was "really a Saudi/Muslim 'plant' in the White House." Ricketts added his own commentary when forwarding the email to a friend, writing, "My impression is that the President is more sympatric [sic] to Muslims than Christians/Jews. We are a Christian country and I feel like this is just a continuation of the assault on Christianity in America."

He also routinely indicated that he had been amused by the racist jokes sent to him by others, deeming one where the punchline was a racial slur to be a "great laugh."

The emails show that Ricketts's beliefs were met with some resistance from his own family. In one 2010 exchange, Pete Ricketts, now the governor of Nebraska, responded to a fearmongering chain email about Muslims by recommending that his father do some research on Snopes before passing such stories along.

"Thanks Peter," the elder Ricketts replied. "However, I think Islam is a cult and not a religion."

On Tuesday, Ricketts's remarks were condemned by Major League Baseball, which said in a statement that the emails were "extremely offensive and completely at odds with the values and principles of Major League Baseball," but allowed that many had not originally been written by Ricketts himself.

Chicago Mayor Rahm Emanuel - who tangled with the Ricketts family in 2012 after Joe Ricketts reportedly weighed spending millions of dollars on an ad campaign that would attack Obama by linking him to his former pastor, Jeremiah Wright - was much harsher in his criticism.

"Joe Ricketts once said that I do not share his values," Emanuel wrote in a statement posted on his Twitter account on Tuesday. "Truer words were never spoken. The ignorance and intolerance he has espoused are not welcome in Chicago. Those are not the values I learned from my parents, and those are not the values Amy and I have instilled in our children. Joe Ricketts should consider himself lucky he has never met my mother. She would teach him a lesson. I am proud not to share his bigoted opinions. Hate has no home in Chicago."

Hours after Splinter published the emails on Monday, Ricketts posted a brief apology on his personal website. "I deeply regret and apologize for some of the exchanges I had in my emails," he wrote. "Sometimes I received emails that I should have condemned. Other times I've said things that don't reflect my value system. I strongly believe that bigoted ideas are wrong."

The Cubs quickly scrambled to distance themselves from his remarks, averring that Ricketts was not directly involved with the organization. According to the Chicago Tribune, Ricketts's four children - Tom, Laura, Pete and Todd - own the team. Tom, a former investment banker, serves as the team's chairman, giving him the most prominent leadership role within the family.

"We are aware of the racially insensitive emails in my father's account that were published by an online media outlet," Tom Ricketts said in a statement shared with ESPN on Monday. "Let me be clear: The language and views expressed in those emails have no place in our society."

While Joe Ricketts may have engineered the purchase of the Cubs, his son made a point of downplaying his role in the franchise.

"My father is not involved with the operation of the Chicago Cubs in any way," the club's chairman said in his statement. "I am trusted with representing this organization and our fans with a respect for people from all backgrounds. These emails do not reflect the culture we've worked so hard to build at the Chicago Cubs since 2009."

Local sports columnists and radio hosts expressed some skepticism about the argument that Joe Ricketts didn't really represent the Cubs on Tuesday, pointing out that it was well-known that he wasn't in charge of the Cubs' daily operations, and that there was no question that he had bankrolled the purchase of the team.

"Old Joe may not have a day-to-day role in running the Cubs, but he's cashing ownership checks," wrote Chicago Sun-Times columnist Steve Greenberg. "Unless and until that ceases, his gilded offspring should be questioned at every turn about what steps they are taking to make Cubdom a brighter, better place for all."

At the Tribune, Rex Huppke chimed in: "They can say it has nothing to do with the Cubs all they want. But without taking serious action to address this level of intolerance, a lot of Cubs fans and Chicagoans in general will be left to wonder just how far the apples fell from the tree."

Muslim community leaders, too, suggested that the team needed to prove that its owners don't share Ricketts's worldview. Hussain, of the Muslim Community Center, wrote in his open letter that the team's official statement "has the ring of PR or 'damage control' for most Muslims and others of good conscience in Chicago" and suggested that the Cubs "make amends in a more genuine, meaningful and demonstrative manner."

Ahmed Rehab, the executive director for the Chicago chapter of the Council on American-Islamic Relations, said at a Tuesday news conference that Tom Ricketts and the Cubs' leadership had reached out to them after the emails were published, and that a face-to-face meeting was in the works. Still, he said, his group wanted to see the team take concrete actions to "recommit to the anti-bigotry values of Chicago."

In an open letter that had been retweeted hundreds of times by Wednesday morning, one Muslim fan suggested that the team could begin by hosting a Muslim American night with halal food and space for prayer, like the New York Mets did in October.

"My life as a baseball fan is intertwined with my existence as a Muslim America[n]," Rimsha Ganatra wrote. "Before every game of the 2016 World Series I spent an extra 30 minutes praying for the Cubs to win. I went to a Cubs game last summer where Louie at the front gate met me with the traditional Muslim greeting and let me know to come to him if anyone gave me trouble for my head scarf [ . . .] These are the fan experiences I want for current and future generations of Muslim American baseball fans to encounter, not the views unearthed by Joe Ricketts today."