Ex-OVG CEO Tim Leiweke Is Getting a Taste of What Life Is Like Under Indictment

Former Oak View Group CEO and longtime sports-entertainment executive Tim Leiweke is asking a federal judge for permission to travel to Canada for business next month — a routine motion on paper that underscores how sharply life changes once an executive is indicted in federal court.

According to an unopposed motion filed Tuesday (Oct. 21) in the U.S. District Court for the Western District of Texas, Leiweke has requested permission to travel to Toronto and Hamilton, Ontario, where his company is developing a major arena and entertainment district project. Hoping to be in Canada from Nov. 17-22 to attend business meetings connected to his Denver-based development company Oak View Group (OVG), the filing notes that Leiweke previously surrendered his passport to pre-trial services in Denver but needs temporary access to travel abroad. His probation officer and the U.S. Department of Justice have both indicated they do not oppose the request.

Leiweke, 68, was arraigned in July and pleaded not guilty to a single count of violating the Sherman Antitrust Act, a charge that carries a maximum penalty of 10 years in prison and a $1 million fine. The case stems from a federal grand-jury indictment alleging that Leiweke and executives from Legends Hospitality conspired to rig the bidding process for the Moody Center, a $375 million arena project at the University of Texas in Austin that opened in 2022. Leiweke’s defense has strongly denied any wrongdoing, arguing that OVG and Legends worked independently and that the DOJ is misapplying antitrust law to a deal that, in practice, produced one of the most successful university-arena partnerships in the country.

“Tim and OVG won in Austin by competing fair and square and they delivered fantastic value and a world class arena to the university,” a spokesperson for Leiweke tells Billboard.

Earlier this month, Leiweke’s attorney, David Gerger, filed a separate motion seeking to delay the trial until at least October 2026, citing the need to review more than seven million pages of evidence turned over by prosecutors. Gerger also signaled that the defense will challenge the government’s interpretation of antitrust law as applied to the Moody Center deal.

“Life Doesn’t Go On as Normal”

While Leiweke continues to run his private ventures, his day-to-day life is now dictated by court supervision. To understand what that looks like, Billboard spoke with Justin Paperny, director of White Collar Advice, a Los Angeles-based firm that coaches high-profile defendants through the pre-trial and sentencing process.

“Life doesn’t go on as normal, not when you have a pre-trial services officer to report to,” Paperny said. “You’re under the microscope of the United States government. They don’t view you as a law-abiding citizen anymore — they view you as someone who broke the law. Traveling internationally, even to Canada, becomes very difficult.”

Paperny, a former stockbroker who himself served time in federal prison (for stock fraud) and who has attended more than 1,500 sentencing hearings nationwide, said the first shock for most white-collar defendants is how restrictive their world becomes overnight. “Every trip has to be approved. Every contact with law enforcement has to be disclosed. For entrepreneurs used to running the show, it’s a massive adjustment,” he said.

Even seemingly minor infractions — a missed call, a traffic ticket not reported — can lead to problems with pre-trial services. “If you get off to a good start, things go smoothly,” Paperny said. “But if you violate even small conditions, the government loses trust quickly.”

Paperny describes the process as bureaucratic but rigid. Defendants on bond must check in regularly with probation officers, report changes in residence or employment, and request written approval for all travel outside their home district.

“You’re dealing with a bureaucrat who has a job to do,” he said. “They’ll ask about mental-health issues, substance abuse, where you live, what you earn, and they’ll lay out very specific conditions. It’s black and white: if you follow them, things can be fine. If not, you’ll feel the consequences.”

Leiweke’s motion illustrates the point. His lawyers note that he previously received permission to travel to Europe this summer and complied fully with court orders, returning his passport immediately upon re-entry. Still, every trip requires a fresh petition, paperwork and the sign-off of multiple agencies. “It’s an enormous inconvenience,” Paperny said. “For someone used to doing deals across continents, the red tape is relentless.”

Paperny said travel to Canada is especially difficult for anyone under indictment. “Canada doesn’t like felons or people facing charges,” he says. “Even with a judge’s permission, the country may deny entry. It wouldn’t surprise me if he never sees Canada again during this process.”

The restriction often comes as a shock to executives used to global mobility. “I’ve been invited to work in Toronto multiple times and still can’t go [because of my conviction],” Paperny says. “It’s not personal — it’s just policy. They’ll arrest you at the border and send you back.”

Beyond managing restrictions, Paperny said the smartest defendants treat the pre-trial period as an opportunity to build credibility with the court. “The question isn’t just what you did — it’s what you’re doing now,” he says.

Paperny’s firm encourages clients to create what he calls “assets”: tangible contributions that demonstrate accountability and reform. “You don’t just tell a judge you’ve changed; you show them,” he explains. “That could be writing a book, starting a blog, mentoring others or creating a course that helps people. Judges want evidence that you’re using your time constructively.”

Paperny believes these proactive steps often have real impact at sentencing. “We’ve had clients whose efforts to create value for others literally changed the outcome of their case,” he says. “Judges and prosecutors are human — they respond to genuine progress.”

For now, the case moves slowly. The court has not yet ruled on Leiweke’s travel request, though the government’s lack of opposition suggests it is likely to be approved. The larger trial delay motion remains pending, and legal observers say the defense’s strategy may hinge on narrowing the scope of what the government can present as collusion.

Meanwhile, Leiweke continues to serve as chairman of his own firm, advising on arena and stadium developments around the world. The irony, Paperny notes, is that while Leiweke still operates at the top of the business, his movements and activities remain closely monitored by federal authorities.

“He has to focus on what he can control — his conduct, his compliance, his contribution,” Paperny said. “That’s what will ultimately define how this story ends.”