Sinclair Broadcast Group hired a group of Republican lobbyists last month as the Federal Communications Commission (FCC) put its proposed merger with Tribune Media in jeopardy, according to disclosure forms released this week.

The filings show that Sinclair tapped the lobbyists to advocate for the embattled merger on June 19, three days after FCC Chairman Ajit Pai (R) said he had “serious concerns” about the deal and would be referring it to an onerous administrative law proceeding.

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The hire is notable for the conservative-leaning media company, which had not hired an outside lobbyist since 2000. Sinclair typically relies on industry trade groups like the National Association of Broadcasters to advocate for its interests.

The hires may be too late to save the $3.9 billion Tribune deal.

On the day that Sinclair hired the group, the FCC released an order accusing the company of trying to mislead regulators about several proposed sidecar deals aimed at bringing the combined broadcasting giant into compliance with media ownership restrictions.

The commission said that the questionable deals involved selling highly valuable stations for below-market value prices to buyers with close ties to Sinclair executives, while still allowing Sinclair to control much of the stations’ operations.