Yesterday was the last day for critics to urge the Federal Communications Commission to stop conservative Sinclair Broadcast Group’s proposed acquisition of Tribune Media Company. President Donald Trump’s administration, which frequently tries to promote right-wing outlets as part of its war on the mainstream press, has bent over backward in order to reward Sinclair for its favorable coverage, while the merger has drawn criticism from consumer watchdogs like Allied Progress and media consolidation foes like Free Press. But they aren’t the only ones objecting: Some pro-Trump media companies have also taken sides against the merger because they worry Sinclair’s growth will impact their own bottom lines, forcing the administration to choose between its staunchest press allies.

Sinclair is already the nation’s largest local news provider, thanks to its ownership of 173 broadcast television stations in communities across the country. If its attempt to purchase Tribune’s 42 broadcast television stations is approved by the Federal Communications Commission (FCC), the result would be a broadcast goliath reaching more than seven in 10 U.S. television households -- nearly double the audience cap mandated by Congress. The deal would have been unthinkable if Trump-appointed FCC chairman Ajit Pai hadn’t rolled back a key Obama administration regulation in April that had prevented Sinclair from further expansion.

The merger raised the hackles of NewsMax Media Inc, which owns a right-wing cable channel and website and has called for the FCC to slow down the process and seek additional information. In a filing, the company warned that the prospect of a combined Sinclair-Tribune company raises “serious competitive concerns” and that “press freedom and media diversity may be seriously harmed by this transaction.” NewsMax CEO Christopher Ruddy has said that the deal raises “so many serious concerns about the concentration of media power.”

The conservative cable news channel One America News Network (OANN) also wants to delay the sale, telling the FCC that the “transaction raises competitive concerns and questions of law.”

Rupert Murdoch’s 21st Century Fox is one player that did not weigh in during the comment period. Sinclair’s increasing power in the conservative media space could prove a threat to Fox News. But Fox also owns dozens of broadcast stations, and the FCC’s deregulation bent could also benefit the company’s own expansion plans. Instead of taking its would-be rival on at the FCC, Fox is reportedly considering dumping Sinclair as an affiliate partner.

As for Trump, he wants to help Sinclair because the network has been a key media ally. After several cycles of support for Republican presidential candidates, the network stepped up its game in 2016, making a deal with the Trump campaign during the election cycle by providing positive coverage in exchange for access. After the election, Sinclair hired a former Trump adviser and required every one of its stations to regularly run his pro-Trump propaganda segments. Sinclair’s conservative “must-runs” are every bit as slanted as Fox News coverage, but Sinclair is more insidious because its viewers don’t expect that level of ideological content from their local news channels. Because so many Tribune media stations are located in big cities and swing states where Sinclair didn’t previously have a platform, the merger could provide a sizeable benefit to Trump’s re-election campaign.

But NewsMax has also been a staunch supporter of the president -- in fact, it was one of Trump’s first real media allies in his political rise. The would-be Fox rival started giving him a platform as early as 2006 and regularly promoted a potential Trump run for president during the 2012 cycle. Described by reporters as the “Trump whisperer” and the administration’s “Zelig,” Ruddy is a close friend of the president who regularly advises Trump and his aides and is often quoted by reporters and appears on cable news as a kind of unofficial spokesperson. In turn, the Trump presidency has been good for NewsMax, which has received unprecedented access; during his first 48 press briefings as White House press secretary, Sean Spicer called on the network’s correspondent more than any other reporter but Fox’s representatives.

OANN, another would-be Fox, is no slouch either -- as The Washington Post noted, the network became “one of President Trump’s favorite media outlets” because its coverage depicts his administration as “a juggernaut of progress, a shining success with a daily drumbeat of achievements.” OANN White House correspondent Trey Yingst was one of Spicer’s go-to questioners, and Trump called on him at a January press conference.

Trump has sought to lift up conservative news outlets throughout his tenure. But as the OANN and NewsMax filings demonstrate, in this fractured media environment, he can’t help one of his media allies without hurting the others.