In 2023, amid the impact of cord-cutting and other upheavals in the market, Diamond Sports Group filed for Chapter 11 bankruptcy protection.

[13][14] The group's other sports properties included Stadium—a national sports network distributed via over-the-air digital television and internet streaming (in partnership with the Chicago White Sox's investment arm Silver Chalice), Tennis Channel, as well as Marquee—a then-upcoming RSN devoted to the Chicago Cubs.

[15] On May 3, Sinclair officially announced that via its subsidiary Diamond Sports Group, it had agreed to purchase the networks for $10.6 billion, pending regulatory approval.

At the same time, it was also revealed that Allen Media Group would hold an equity stake in the company and serve as a "content partner".

[17] Due to a clause in the original sale,[18] Yankee Global Enterprises had a right of first refusal to purchase Fox's share in YES Network.

[26] The next day, Sinclair announced that it had entered into an agreement with casino operator Bally's Corporation to acquire the naming rights under a 10-year deal.

Executive vice president Michael Connelly explained that the configuration was designed to eventually allow for the integration of sports betting-related information such as lines and props.

[36] During its bankruptcy, Diamond has missed payments to the Arizona Diamondbacks, Texas Rangers, Cleveland Guardians and Minnesota Twins of Major League Baseball (MLB), the Arizona Coyotes of the National Hockey League (NHL), the Orlando Magic of the National Basketball Association (NBA), and to Raycom Sports for its ACC on Regional Sports Networks package and the Orange Bowl for its Orange Bowl Classic men's college basketball tournament.

[37][38][39][40][41][42][43] Diamond also entered grace periods for their payments to the San Diego Padres and Cincinnati Reds of MLB, which they eventually made.

[46][47] On June 1, 2023, after a two-day long hearing, the bankruptcy judge ordered Diamond to pay the other Major League Baseball teams they missed payments to fully within five days.

[56][39] On December 30, 2023, the Atlanta Hawks and New Orleans Pelicans reached agreements with Gray Television to air 10 over-the-air games in local markets.

[67] On July 29, 2024, Comcast reached a new carriage agreement, allowing Bally Sports to be carried on the Xfinity "Ultimate TV" tier rather than on the basic service.

[68] On August 23, 2024, Diamond Sports announced it had reached amended regional broadcast agreements with nine NHL teams and thirteen NBA teams through at least the 2024–25 season, including reductions to rights fees; the agreement will expire if Diamond Sports Group's bankruptcy plan is not approved by the court.

[73] The Cleveland Guardians, Milwaukee Brewers, Minnesota Twins, and Texas Rangers' contracts with Diamond expired at the end of their 2024 regular seasons.

[74][75][76] On October 8, 2024, MLB Local Media announced that it would assume the rights to the Brewers, Guardians, and Twins beginning in the 2025 season.

[88] On November 14, 2024, after MLB and the Atlanta Braves withdrew their objection, Diamond's reorganization plan was approved by the bankruptcy court.

The company also announced that it had successfully renegotiated with the Braves, Tigers, Angels, Marlins, Cardinals, and Rays to stay on FDSN.

[90] Following the approval of its reorganization, Diamond re-engaged with the Brewers and Reds; on December 31, 2024 and January 13, 2025 respectively, both teams announced that they would forego their previously-announced partnerships with MLB Local Media, and would remain on FDSN under new contracts in the 2025 season.

In December 2020, Sinclair announced plans to launch a direct-to-consumer streaming service based around the linear Bally Sports networks.

The service was originally targeted for a 2021 launch, though it was delayed due to Bally Sports needing to negotiate over-the-top streaming rights with the teams.

[108] Sinclair CEO Chris Ripley stated that the service was meant to target cord cutters, whom the company felt were underserved in the regional sports market.