IMO, the three biggest problems Diamond had were:
1. Being dropped by DISH Network, which actually happened before their purchase. Diamond was betting on being able to get back on Dish, and failed at that.
2. Covid-19 and the shortened NBA, MLB and NHL seasons in 2020-21 that impacted both ad sales and subscription revenue.
3. Lots of expensive debt. Some of the debt used to finance the purchase bore an interest rate above 10%. Expensive debt in a business where revenue isn't growing rapidly is a big challenge.
Sinclair is also a pro Trump broadcaster and I could connect the dots on how Makan Delarhim judges media mergers:
1. Fox was supposed to focus on news and sports so why bailing out splitting the RSNs instead of keeping them in regards to regulatory concerns surrounding their national sports divisions.
2. Sinclair is largest ABC and Fox affiliate group with Disney only has 8 O&O stations. They didn't swap their RSNs for stations and didn't guarantied to have the RSNs and Tennis Channel to be carried on Hulu (which is part of the Disney-Fox merger).
3. Sinclair snatched the rights to most Chicago Cubs games but it was a revenge deal to counter against Nexstar which successfully bought WGN's owner Tribune Media. They had a lawsuit against Tribune Media but Nexstar settled by acquiring 2 Sinclair stations in Lexington and Rio Grande Valley.
4. Trump praises Sinclair, Trump hates CNN, Delarhim was pointless to the media industry being disrupted by Big Tech. Everyone in the Hollywood community including unions and guilds largely opposed Disney's merger with Fox so does the repeal of the Paramount Consent Decrees. Delarhim tried to block ATT-WM merger despite Trump's tirades with WM owned CNN but failed in the Supreme Court while he approves the Disney-Fox merger with a condition to divest the RSNs to Sinclair while rejecting the concerns over the massive large market share in cinemas by 40 percent in 2019.
5. When will Bryon Allen with react to this bankruptcy if they continue to buy more TV stations if available, Sinclair might reduce the number of sidecar firms the Sinclair provided LMA since FCC rules don't allow duopolies between 2 Big Four stations in regards to the ratings among Top 4 TV stations in terms of newscasts.
If u connect those dots, it's all about the Trump politics and increase of market power while rejecting democratic concerns in how Delarhim is useless in terms of of his view of Big Media and Big Tech so does M&A. It's time for Delarhim to be accountable on how he failed to counter Big Tech disrupting Big Media.