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TALLAHASSEE — Saying the case holds “massive importance for the future of online gaming across the country,” two pari-mutuel companies have asked the U.S. Supreme Court to block a 2021 deal giving the Seminole Tribe control over sports betting in Florida.

The companies last week sought Supreme Court review of an appellate court’s decision upholding the deal, which could reap Florida at least $2.5 billion over the next five years and is also the subject of a legal challenge at the Florida Supreme Court.

Lawyers for West Flagler Associates and Bonita-Fort Myers Corp. filed the petition at the U.S. Supreme Court less than a month after the tribe paid nearly $58 million to the state in the first installment of a revenue-sharing agreement after the Seminoles launched mobile sports betting in November.

The federal lawsuit is focused on part of the 2021 deal between the tribe and the state that allowed the Seminoles to control sports betting throughout Florida. The deal said bets “using a mobile app or other electronic device shall be deemed to be exclusively conducted by the tribe.”

U.S. Department of the Interior Secretary Deb Haaland, whose agency oversees tribal gambling, allowed the deal, known as a compact, to go into effect. But the Florida companies challenged her decision, arguing that the compact violates a federal law known as the Indian Gaming Regulatory Act, or IGRA, because it authorizes gambling off tribal lands.

A federal district judge agreed with the tribe in 2021, but a three-judge panel of the U.S. Circuit Court of Appeals for the District of Columbia in June reversed her ruling. The companies turned to the Supreme Court after the full appellate court refused to reconsider the panel’s decision.

The companies also contend the “hub-and-spoke” sports-betting arrangement with the Seminoles violates a state constitutional amendment requiring voter approval of gambling expansions, an issue that is the focus of the Florida Supreme Court case.

In the petition filed Thursday at the U.S. Supreme Court, lawyers for the companies argued that nothing in federal law allowed Haaland to approve a compact “that provides for gaming off Indian lands. The compact at issue here clearly provides for gaming off Indian lands.”

The sports-betting part in the compact was used “as a backdoor around state constitutional prohibitions against online sports gambling conducted off tribal lands” and created “a sports gambling monopoly” for the tribe, the petition said.

“This question is exceptionally important not just for the people of Florida, but for the nationwide

precedent it will set for other state-tribal compacts if the Court of Appeals’ affirmative answer is left undisturbed — as an end-run not just around state-law prohibitions on gaming off tribal lands, but also around Congress’ limitation of IGRA’s federal imprimatur to gambling on tribal lands,” Hamish Hume, an attorney with the Boies Schiller Flexner firm, wrote.

Hume pointed to U.S. District Judge Dabney Friedrich’s November 2021 ruling, which called the sports-betting plan a “fiction” and invalidated other parts of the agreement.

The appellate court’s decision overturning Friedrich’s ruling “allows Florida and the tribe to have their cake and eat it too,” Hume argued.

“The whole point of the compact is to provide a hook for dodging Florida’s constitutional requirement of a popular referendum to approve off-reservation sports betting,” Hume wrote.

The companies’ petition urged the federal justices to “correct” the appellate court’s “erroneous affirmation” of Haaland allowing the compact to move forward, saying the issues raised in the case “are of massive importance for the future of online gaming across the country — and can only be conclusively resolved by this (Supreme) Court.”

In September, the companies filed a petition with the Florida Supreme Court alleging that the compact runs afoul of the 2018 constitutional amendment requiring voter approval of expansions of casino-style gaming. Isadore Havenick, an owner of the pari-mutuels whose family has operated gambling facilities in Florida for more than 60 years, also is a plaintiff in the state challenge. The plaintiffs argued the federal appellate rulings resulted in an “urgent” situation necessitating state Supreme Court review, but in November justices refused the plaintiffs’ request to expedite the case.

Gov. Ron DeSantis negotiated the compact with the tribe, and the Legislature ratified the deal.

Lawyers for DeSantis and legislative leaders have asked the state Supreme Court to reject the challenge for a number of reasons. In a brief filed in December, lawyers for the state argued, in part, that sports betting “is not ‘casino gambling’ as that term is defined in the Florida Constitution.”

The brief dug into part of the amendment that defined casino gambling as “the types of games typically found in casinos.” It said “the types of games typically found in casinos was fixed at the time” the constitutional amendment passed — and that those games did not include sports betting.

West Flagler holds three jai alai licenses and Bonita-Fort Myers Corp. does business as Bonita Springs Poker Room in Southwest Florida. The companies allege the Seminoles’ sports-betting operations will have a negative impact on their revenue.

Under the three-decade compact, the Seminoles agreed to pay Florida about $20 billion, including $2.5 billion over the first five years of the agreement.

The deal also authorized the Seminoles to offer craps and roulette at their casinos and to add three casinos on tribal property in Broward County. It also allowed pari-mutuels to contract with the Seminoles and share revenue from sports betting.

The tribe in November rolled out a sports-betting app and in December launched craps and roulette at its casinos.

The tribe on Jan. 18 paid nearly $57.8 million to the state in its first monthly payment in the deal. Monthly payments will fluctuate over the coming months as the tribe and the state work out details of the revenue-sharing calculation for the year, Amy Baker, coordinator of the Legislature’s Office of Economic & Demographic Research, told The News Service of Florida on Tuesday.