In a longstanding legal soap opera rife with unexpected twists, the case involving the launch of mobile sports betting in Florida encountered another one Monday afternoon.

Attorneys for West Flagler Associates filed an application with the U.S. Supreme Court for an extension to submit an application for a writ of certiorari. WFA, a Florida parimutuel operator, brushed up against a deadline Monday evening to submit the application with the nation’s highest court. In a seven-page letter submitted to the court, attorneys for the operator requested an extension until Feb. 9.

The parimutuel operator seeks to overturn a June ruling from the U.S. Court of Appeals for the District of Columbia, which provided the first twist in the legal drama. In that ruling, the federal appellate court reversed a November 2021 decision from U.S. District Court Judge Dabney Friedrich, who deemed a compact between the state of Florida and the tribe to be illegal.

As the U.S. high court weighs whether to accept the case, a litany of tribal gaming insiders nationwide will be paying close attention.

On the federal level, WFA has exhausted nearly all of its legal options, necessitating the anticipated petition to the Supreme Court. Hard Rock Bet, the sports betting app of the Seminole Tribe of Florida, unexpectedly relaunched earlier this month, several weeks before an anticipated rollout near Thanksgiving Day. WFA, the owner of Magic City Casino in South Florida, previously had a motion denied by the Supreme Court this fall when it sought to keep the Hard Rock platform offline before the court might even hear the case.

By taking its case to the U.S. Supreme Court, West Flagler is seeking to prevent the Seminole Tribe from gaining a virtual monopoly on online sports wagering in the state.

The Seminoles currently offer sports betting on a limited basis in the nation’s largest state with legal sports wagering. In May 2021, the Florida Legislature and the Seminole Tribe agreed to a new compact that included the tribe’s ability to take sports bets in the Sunshine State in addition to expanding its casino gambling.

The compact called for disbursement by the tribe of $2.5 billion to the state over a five-year period. The agreement included a so-called “hub-and-spoke” model under which Florida gamblers could place sports wagers anywhere statewide that were deemed allowed by going through a server located on Seminole tribal land.

After the compact was signed by Florida Gov. Ron DeSantis, it went to the U.S. Department of the Interior for approval. Instead of formally approving the compact, Interior Department Secretary Deb Haaland allowed for a requisite 45-day waiting period to pass without taking action. In doing so, Haaland essentially allowed the Class III gaming compact to be deemed as approved.

That decision led to the ongoing legal volley that began in July 2021. WFA, along with Bonita-Fort Myers Corp., a Florida poker room, filed a federal lawsuit claiming that the compact violated the federal Wire Act of 1961 and the Unlawful Internet Gambling Enforcement Act (UIGEA) of 2006. The parties also took exception with language within the Indian Gaming Regulatory Act (IGRA), a statute enacted by Congress in 1988.

Indian tribes have the exclusive right to regulate gaming activity on Indian lands if the gaming activity is not specifically prohibited by Federal law and is conducted within a State which does not, as a matter of criminal law and public policy, prohibit such gaming activity.

—The Indian Gaming Regulatory Act: Chapter 29, §2701. Findings

By November 2021, WFA scored a victory in U.S. District Court when Friedrich found the compact to be in violation of IGRA. In issuing the ruling, Friedrich noted that while “the Tribe failed to show that this Court’s decision will cause irreparable harm,” the plaintiffs continued to face “ongoing competitive injury” since the compact granted the Seminoles a near monopoly over mobile sports betting.

The Seminoles appealed the decision to the U.S. Circuit Court for the the District of Columbia, which heard oral arguments last December. Rachel Heron, an attorney who appeared on behalf of the Interior Department, faced questions from a three-judge panel on whether an Interior Department secretary has an obligation to reject a state compact that is inconsistent with IGRA.

In response, Heron noted that a secretary such as Haaland has the authority to disallow a compact that contradicts federal law, but she is not mandated to do so. Hamish Hume, an attorney for the parimutuels, argued that IGRA only applies to gaming activities that take place on tribal lands. Under one interpretation of IGRA, wagers placed inside Hard Rock Stadium, the home of the NFL’s Miami Dolphins, are off-site bets because the venue is built on non-tribal land. Proponents of the argument maintain the same view for wagers that are processed through a server located on a tribal reservation.

— Sports Handle (@sports_handle) August 31, 2023

In June, roughly six months later, the appellate court unanimously reversed Friedrich’s decision. It found that IGRA does not prohibit a gaming compact between a tribe and a state from discussing other topics, namely activities that fall “outside Indian lands.” The new compact between the state and the Seminoles also enables the tribe to add table games such as roulette and craps at its retail casino properties.

According to U.S. federal law, West Flagler had a 90-day window to file the application for writ of certiorari, a period that began in September. Unless the extension is granted, the period for submitting an application will expire on Dec. 11, the first business day after the 90th day from the denial of a rehearing. In Monday’s filing, attorneys for WFA articulated nearly a dozen of reasons why an extension should be granted.

In a separate case on the state level, the Florida Supreme Court last Friday denied a motion that sought to force the Seminoles to shut down the Hard Rock online sports betting platform. The ruling potentially sets the stage to allow Hard Rock to move out of a soft launch and into a full rollout. The Florida Supreme Court also set a Dec. 1 date for representatives of DeSantis and the Florida Legislature to respond to a West Flagler complaint.

Neither Hume nor representatives for the Seminole Tribe immediately responded to requests from Sports Handle for comment on Monday.

If the Florida Supreme Court rules in favor of West Flagler’s state petition, such a ruling will impact the scope of the applicants’ petition for a writ of certiorari, attorneys for WFA wrote in Monday’s U.S. Supreme Court filing. But if the Florida court rules against the parimutuel, the “statutory and constitutional issues” raised previously by Judge Friedrich’s opinion would remain, they contend. Accordingly, there is a possibility that the application for writ of certiorari could be “significantly informed,” by the decision of the Florida Supreme Court, the attorneys argue.

— Daniel Wallach (@WALLACHLEGAL) November 20, 2023

The Supreme Court receives about 10,000 applications a year, according to the Judicial Learning Center, an organization committed to promoting public understanding of the judicial branch of the government. Using the so-called “rule of four,” the U.S. high court will issue a writ of certiorari if four of its nine justices determine that a case has value.

Nevertheless, the court takes up only a small percentage of cases, as it hears fewer than 100 cases a year, according to the center.