The star-crossed fate of Diamond Sports Group is a well-known saga to faithful readers of The Varsity and avid consumers of the regional sports network cinematic universe. But for the uninitiated, allow me to retell a gruesome story in brief: Diamond, once the under-loved leftovers of Rupert Murdoch’s $70+ billion sale of the 21st Century Fox assets to Disney, had been left for dead amid the underwater economics of the local sports broadcasting business—one in which its rights payments overwhelmed its local TV revenues. A year ago, the company filed for bankruptcy. Then, in mid-January, came a lifeline: Diamond worked out a $115 million deal with Amazon, combined with a $450 million debtor-in-possession financing from its creditors. 

Now, the hard part truly begins. In order to satisfy its creditors, Diamond needs to secure long-term deals with three of the country’s biggest distributors (Comcast, Charter, and DirecTV) while working out agreements with the NBA and NHL to distribute games in local markets. Closing any of these deals requires a high degree of execution. Closing them all virtually simultaneously amid the financial pressures is a Herculean task. Nevertheless, Diamond has to file its business projections to the bankruptcy court before a hearing scheduled for April 17. “We were able to enjoy it for 24 hours,” Diamond C.E.O. David Preschlack said about signing the Restructuring Support Agreement in January. “Then we needed to start preparing to scale Mount Everest again.”