The lawsuit seeks compensation for all losses Tribune Media incurred during the attempted transaction.
Tribune pointed to the same problems that the FCC found in Sinclair's proposal to divest some stations in order to stay under federal ownership limits.
"In light of the FCC's unanimous decision, referring the issue of Sinclair's conduct for a hearing before an administrative law judge, our merger can not be completed within an acceptable timeframe, if ever", said Tribune Media CEO Peter Kern, in a statement.
Sinclair initially announced plans to buy the media conglomerate fifteen months ago.
As a result, Sinclair planned to sell off 21 of its stations.
Sinclair refused to sell stations in the markets as required to obtain regulatory approval, according to Tribune's release, prompting the FCC to put the merger on indefinite hold.
In the lawsuit filing (via CNN), Tribune alleges that Sinclair "repeatedly and willfully breached its contractual obligations in spectacular fashion".
The merger would've created the largest local broadcaster in America. Tribune is seeking an amount "including but not limited to approximately $1 billion of lost premium to Tribune's stockholders and additional damages in an amount to be proven at trial".
Wednesday was the first day Tribune was allowed to pull out of the deal, per the merger agreement.
The Maryland company did not immediately respond early Thursday to a request for comment from The Associated Press. In Los Angeles, they own KTLA channel 5 and in Chicago, they own WGN TV.
There was still a slim chance that Sinclair could save the merger because the FCC referred the deal to an administrative law judge.
Sinclair is the nation's largest local broadcaster, reaching about 4 in 10 USA households through TV stations.
The backstory: The deal was thought to be a sure thing, but the FCC threw a wrench into it after Chairman Ajit Pai, who is favorable to industry consolidation, raised questions about the validity of some of the deal terms provided to the commission by Sinclair.
Sinclair has defended the decision to have its anchors read from the same script across the country as a way to distinguish its news shows from unreliable stories on social media.
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