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Brothers Osborne have received five Academy of Country Music Awards, four Country Music Association Awards, and seven Grammy nominations.
The company expressed hope that the vaccine rollouts will speed the return of concerts this year.
Only after receiving a full commercial casino license could Empire City also be licensed for sports betting.
"Ninety percent of our revenue is from ticket sales," said Executive Director Hugh Hallinan
The 1,447-seat Bridgeport theater is undergoing upgrades that will enable it to host more concerts and to present special film screenings.
Among the questions still to be addressed is how the new concert venue will peacefully coexist with the Webster Bank Arena next door.
The legendary rock band Chicago sold out the 1,590-seat theater in late September, while this month will see such diverse offerings as stand-up comic Lewis Black and Food Network personality Alton Brown.