WASHINGTON — The day before President Trump’s inauguration, the top executive of the Sinclair Broadcast Group, the nation’s largest owner of television stations, invited an important guest to the headquarters of the company’s Washington-area ABC affiliate.
The trip was, in the parlance of the business world, a deal closer.
The invitation from David D. Smith, the chairman of Sinclair, went to Ajit V. Pai, a commissioner on the Federal Communications Commission who was about to be named the broadcast industry’s chief regulator. Mr. Smith wanted Mr. Pai to ease up on efforts under President Barack Obama to crack down on media consolidation, which were threatening Sinclair’s ambitions to grow even bigger.
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Mr. Smith did not have to wait long.
Within days of their meeting, Mr. Pai was named chairman of the F.C.C. And during his first 10 days on the job, he relaxed a restriction on television stations’ sharing of advertising revenue and other resources — the exact topic that Mr. Pai discussed with Mr. Smith and one of his business partners, according to records examined by The New York Times.
“These are invaluable and effective tools, which were taken away by the commission,” according to a summary of their meeting filed with the F.C.C.
It was only the beginning. Since becoming chairman in January, Mr. Pai has undertaken a deregulatory blitz, enacting or proposing a wish list of fundamental policy changes advocated by Mr. Smith and his company. Hundreds of pages of emails and other documents obtained under the Freedom of Information Act reveal a rush of regulatory actions has been carefully aligned with Sinclair’s business objectives.
The moves, which include easing a cap on how many stations a broadcaster can own, have opened up lucrative opportunities for Mr. Smith, among them a $3.9 billion bid to buy Tribune Media, another large owner of stations.
Mr. Pai’s deregulatory drive has also helped win him a following as a champion of pro-business, conservative causes — even leading some Republicans to approach him since he was first named to the F.C.C. in 2012 about running for elected office.
An examination of the F.C.C. records shows that the Smith-Pai alliance does not follow the familiar script of a lobbyist with deep pockets influencing policy. Instead, it is a case of a powerful regulator and an industry giant sharing a political ideology, and suddenly, with the election of Mr. Trump, having free rein to pursue it — with both Mr. Smith, 66, and Mr. Pai, 44, reaping rewards.
Neither Mr. Pai nor Mr. Smith would comment for this article.
Associates say both men believe that local television stations, which fall under the commission’s rules because they broadcast over federally owned airwaves, are at a disadvantage when competing against cable companies and online streaming services like Comcast and Netflix.
Tina Pelkey, spokeswoman for Mr. Pai, said the new chairman had not taken steps to help Sinclair specifically; his concerns relate to the broadcast industry generally.
“It has nothing to do with any one company,” Ms. Pelkey said.
Other broadcast companies, as well as the National Association of Broadcasters, have pushed for some of the same changes that have benefited Sinclair.
Loosened regulatory requirements, Sinclair executives said, will help even the playing field and benefit millions of Americans who rely on broadcast stations for news and entertainment by allowing the companies to invest in new equipment and technology.
“Thankfully we’ve got Chairman Pai, who’s launched an action to look at antiquated rules,” Christopher S. Ripley, who became Sinclair’s chief executive in mid-January, said in a recent speech, adding that the rules had “artificially tipped the playing field away from TV broadcast.”
But critics say the rollback undermines the heart of the F.C.C. mission to protect diversity, competition and local control in broadcast media. It also gives an increasingly prominent conservative voice in broadcast television — Sinclair has become known for its right-leaning commentary — an unparalleled national platform, as television remains the preferred source for most Americans of news, according to Pew.
A merger with Tribune would transform Sinclair into a media juggernaut, with reach into seven out of 10 homes through more than 200 stations in cities as diverse as Eureka, Calif., and Huntsville, Ala. The company would have a significant presence in important markets in several electoral swing states, including Pennsylvania, Ohio and North Carolina, and would gain entry into the biggest urban markets: New York, Los Angeles and Chicago.
The result would illustrate the real-world stakes of the Trump administration’s pursuit of dismantling regulations across government. The rollback at the F.C.C., a microcosm of the broader effort, pleases business interests and many Republicans who complain that regulators are heavy-handed and hostile in their approach. It raises alarms among free-speech advocates and many Democrats who say consumers suffer without aggressive oversight.
“I worry that our democracy is at stake because democracy depends on a diversity of voices and competition of news outlets,” said Representative Frank Pallone Jr. of New Jersey, the top Democrat on the House Energy and Commerce Committee.
If Sinclair’s past is any guide, the changes for viewers could be profound.
The company has a history of cutting staffs and shaving costs by requiring stations to share news coverage, in that way reducing unique local content. And it has required stations to air conservative-leaning segments, including law-and-order features from its “Terrorism Alert Desk,” as well as punditry from Republicans like Boris Epshteyn, a former surrogate to Mr. Trump, who was still seen visiting the White House after joining Sinclair.
In the political battleground state of Wisconsin, a merger would give Sinclair six stations in the biggest markets — Milwaukee, Green Bay and Madison — causing some journalists to fear a statewide, coordinated corporate news strategy that would tilt right.
“We’ve moved from a high-quality independent news ownership structure to one where a few companies have outsized influence,” said Lewis A. Friedland, a professor of journalism at the University of Wisconsin-Madison.
Mr. Friedland previously worked as a news manager at WITI, the current Fox affiliate in Milwaukee. It is owned by Tribune and would become part of the Sinclair empire if the merger is approved, as expected.
Sinclair rejects suggestions that its stations push right-leaning views, and says the company’s mission is to be objective in its news coverage.
“We are proud to offer a range of perspectives, both conservative and liberal — to our consumers — on our Sinclair broadcast stations each day,” Scott Livingston, Sinclair’s vice president for news, wrote in a July memo to staff members. “It is unfortunate that so many of our competitors do not provide the same marketplace of ideas.”
An Opposition Voice Rises
Though Sinclair is not a household name like the conservative cable TV channel Fox News, it has been a powerful operator in Washington, with a decades-long history of courting Republicans and Democrats even as regulators accused it of flouting broadcast rules.
Sinclair was founded in 1971 by Mr. Smith’s father, Julian Sinclair Smith, an electrical engineer with a deep curiosity about new broadcasting technology. At the time, the company consisted of a radio station and a single UHF station in Baltimore, but it wasn’t long before it embarked on an ambitious growth strategy.
With more stations, Sinclair could command more lucrative advertising, and later, higher fees from cable and satellite companies that retransmitted its broadcasts.
Sinclair helped pioneer a range of creative growth techniques that the company insisted were both legal and good for television viewers.
Most notable was its use of so-called joint sales agreements, which allowed it to work around ownership rules that prevented any one company from owning multiple top-rated channels in a single market.
The practice started in 1991 in Pittsburgh as a game of ownership hot potato, when Sinclair sold its station there to an employee, Edwin Edwards, and retained ownership of a second station. The two stations then shared resources and programming, but on paper they remained under separate ownership. David Smith’s mother, Carolyn Smith, later helped fund Mr. Edwards’s company and took a stake in it.
Consumer advocates long complained about the maneuver, and by President Obama’s second term, regulators at the F.C.C., then led by Democrats, were taking a hard look at it.
That is when, records show, Mr. Pai first met with Sinclair’s top lawyers.
Mr. Pai was a fresh Republican face on the commission. He had an impressive background: degrees from Harvard and the University of Chicago Law School, and stints at the Department of Justice, at the general counsel’s office of the F.C.C. and at the Senate Judiciary Committee, as an aide to Sam Brownback, then a Republican senator from Kansas and now the state’s governor.
The child of immigrants from India, he liked to tell the story of how his parents arrived in the United States with nothing but $10 and a transistor radio.
Perhaps most appealing to Sinclair and other TV station owners, Mr. Pai exhibited blanket empathy for the broadcasting industry, both television and radio.
“I’ve been listening carefully to what you have to say,” Mr. Pai told broadcast executives in late 2012. “Unfortunately, it seems there’s a widespread perception that today’s F.C.C. is largely indifferent to the fate of your business.”
An enthusiastic purveyor of free-market philosophy, Mr. Pai quickly became a dependable opponent to regulations created by the F.C.C.’s Democratic majority. He promised to take a “weed whacker” to regulations if he ever became chairman.
“The commission,” he told the broadcast executives, “can do a better job of focusing on what’s important to broadcasters.”
An Alliance Is Forged
Just seven months into Mr. Pai’s tenure, in December 2012, he welcomed a group of visitors to his office: Barry M. Faber, Sinclair’s general counsel, and two of the company’s Washington-based corporate lawyers.
“Television stations have utilized J.S.A.s for at least 10 years,” Mr. Faber told Mr. Pai according to records of the meeting filed with the F.C.C., referring to the joint sales agreements that Sinclair utilized in Pittsburgh and elsewhere.
Mr. Faber added that “to his knowledge, not a single example of harm to program diversity or competition for viewers resulting from J.S.A.s has been documented.”
The Sinclair executives made the same pitch to the other commissioners, but it was Mr. Pai, the records show, who aggressively picked up the company’s cause in opposing the commission’s crackdown on the disputed agreements.
In two follow-up visits with Mr. Pai’s chief of staff, Matthew Berry, in January and February 2014, Sinclair sent Rebecca Hanson, a lobbyist for the company who had just left a job at the F.C.C.
Federal law prohibits top officials from lobbying former colleagues immediately after leaving government, but Ms. Hanson was not senior enough at the F.C.C. to be subject to the restriction. Agency records show that she met with Mr. Berry, and shared with him data that showed the benefits to consumers of joint sales agreements.
Mr. Pai inserted the information, almost word for word, in his formal legal argument when voting against the F.C.C. measure, in addition to citing experiences at other companies, like Entravision, an owner of Spanish-language television stations. He then echoed arguments made by broadcasters like Sinclair that opposed the move in a series of speeches, remarks before Congress and in social media, where he is a prolific user of Twitter.
Ms. Hanson said the meetings were entirely appropriate, and they were disclosed as required under F.C.C. rules. “Sinclair has followed the rule-making process like everyone else,” Ms. Hanson said in an interview.
Mr. Pai also made appearances on conservative media, extending Sinclair’s arguments beyond telecommunications circles to the broader Republican audience. The advocacy did not go unnoticed. Mr. Pai has been eyed for years by Republican leaders in Kansas and asked at least three times to consider a run for public office, according to two former government colleagues familiar with Kansas Republican politics.
Harold Feld, a senior vice president at the left-leaning consumer advocacy group Public Knowledge, said Mr. Pai had translated his visibility “into enormous influence and a much brighter future” in Republican circles.
“He discovered in the same way Trump discovered that sounding off on things — taking extreme positions, using social media, being the ‘rock star’ — has benefits,” he said.
Still, Mr. Pai’s advocacy did not improve Sinclair’s plight during the Obama years, when rulings repeatedly went against the company. “The F.C.C. continues to bury its head in the sand,” Sinclair’s lawyers wrote to the agency in frustration.
Sinclair also faced two investigations into rule violations.
In July 2016, the F.C.C. announced a $9.5 million fine against Sinclair for violating “good faith obligations” when negotiating fees from cable and satellite companies that retransmit its broadcasts.
A second investigation, which is continuing, deals with commercials aired on Sinclair stations by the Huntsman Cancer Institute, based in Salt Lake City. The commercials were broadcast as news stories on some stations without viewers’ being alerted to the fact that they were paid content.
Emails reviewed by The Times show that Ms. Hanson, the Sinclair lobbyist, reached out to her former F.C.C. colleagues about the Huntsman investigation.
“How can they not tell us what they have against us? Will this ever end? Why won’t they tell us? Can you get them to tell us?” Ms. Hanson wrote on July 26, 2016, to her former boss, William Lake, the head of the F.C.C. media bureau.
“Being on the outside of the F.C.C. is so … weird,” she wrote.
At that point, tensions between the F.C.C. and Sinclair were at a high point.
Mr. Smith, the Sinclair chairman, had shown his own frustration around the same time with the F.C.C.’s investigation of the Huntsman segments. He lashed out during a session in Baltimore with more than 100 news directors and executives.
In an expletive-filled rant, Mr. Smith suggested that Sinclair stations that ran the segments would have to pay for their mistake. He also ordered news directors to write him emails admitting they had erred and outlining what they would do to prevent it from happening again.
“Exciting times, to say the least!” said the email to Mr. Pai’s assistant days after Mr. Trump’s victory in November. It was from Ms. Hanson, the Sinclair lobbyist. “I am sure the commissioner will be in increasing demand in the coming weeks.”
Mr. Pai was widely seen as the top contender to take over as F.C.C. chairman under a Republican administration, and Ms. Hanson had already invited him to speak at a gathering on Nov. 16 of general managers from Sinclair stations at the Four Seasons Hotel in Baltimore.
Now that Mr. Trump had been elected, she was adding another request: “Would he have time to meet with our C.E.O., David Smith, for a few minutes after his session?”
The answer was yes, and Mr. Pai and Mr. Smith, then Sinclair’s chief executive and chairman, met in private at the end of the event.
It is unclear whether the two men had previously met. If not, Mr. Pai would soon learn that Mr. Smith was hardly a conventional television mogul.
Unpolished, gruff and intensely private, he does not belong to the slick world of media elites, where his contemporaries, like Leslie Moonves at CBS and Rupert Murdoch at 21st Century Fox, are staples of the society pages.
His inventory of business investments includes a small chain of pizza restaurants and a farm where he grows 15 varieties of tomatoes.
A frank and adversarial titan of local news, Mr. Smith has on occasion himself become news. In 1996 he and a prostitute were arrested by the Baltimore police in his company Mercedes during a sting operation. And in 2015, a jury awarded a farmer $1.8 million after the farmer sued Mr. Smith for having 95 acres of his cornfield mowed down. The farmer leased the field from Mr. Smith in Monkton, Md., near Sinclair headquarters in Hunt Valley. Mr. Smith prevailed on an appeal.
Mr. Smith and Mr. Pai met for a second time in January, just before Mr. Trump’s inauguration. Mr. Smith was joined by Armstrong Williams, a business partner and Sinclair conservative talk show host, and Mr. Ripley, Sinclair’s newly named chief executive, who later expressed confidence that the F.C.C. under Mr. Pai would enact sweeping regulatory changes.
“We do expect this new F.C.C. to tackle the ownership rules,” Mr. Ripley said on an earnings call with investors in February. “We’re very optimistic about this new F.C.C. and the leadership of Ajit Pai.”
Mr. Smith had already made clear his expectations. “If Donald Trump is as deregulatory as he suggests he is,” Mr. Smith said at a media industry conference just after the election, according to TheStreet.com, “we’re going to be the first industry in line to say, ‘We are the most over-regulated industry that exists in the United States.’”
Neither Sinclair nor the White House would say if Mr. Smith had recommended Mr. Pai for the chairmanship. Either way, Mr. Pai did not disappoint.
In one of his first actions as chairman, he struck down an effort to rein in the use of joint sales agreements, the issue he had discussed with Mr. Smith in January.
Mr. Pai also froze a program for broadband subsidies for low-income families and began a rollback of net neutrality rules that ensured internet traffic was equally available to all consumers, acting on regulatory issues that will reshape other multibillion-dollar businesses under his watch.
Mr. Pai then introduced his most stunning action to date, easing the cap on ownership for broadcast television stations. The order allowed Sinclair to count just half of its UHF stations against the national limit.
Almost immediately, Sinclair took advantage of the relaxed regulation, announcing the purchase of Bonten Media, an owner of television stations, and Tribune.
The proposed merger with Tribune raised broad opposition from consumer groups, former regulators, satellite and cable firms and even conservative media. More generally, the relaxed ownership limits on UHF stations also unsettled some TV and media companies.
“It doesn’t make any sense. It is a sham,” said Jim Goodmon, president of Capitol Broadcasting Company, a small television and radio company in Raleigh, N.C. “It becomes a game of scale and the big guys will have everything.”
But days after the action on the ownership cap, Mr. Pai gave a keynote speech to the National Association of Broadcasters convention in Las Vegas, where he promised to rethink all media ownership restrictions.
“One of the most powerful forces in government is inertia,” Mr. Pai told the group in April. “Rules that get on the books seem to stay there forever,” he added. “I’m trying to change that.”
Sinclair’s viewers heard about Mr. Pai’s performance. Mr. Williams, the conservative commentator, showered Mr. Pai with praise on his show, which is broadcast on Sinclair TV stations nationwide.
“When you ask people who are familiar with you, one of the common themes is that this guy really has courage, he’s really tough, he knows who he is, he understand and respects the law and he has no political agenda,” Mr. Williams said to Mr. Pai during a televised interview, adding, “Where do you find that kind of self-awareness, that kind of courage that propels you?”
Sinclair’s increasingly tight relationship with the F.C.C., and the likelihood that the commission will allow it to grow and spread its conservative agenda further, has made critics, including some longtime television journalists, uneasy.
Jill Geisler, a former vice president at WITI, the Tribune station in Milwaukee, said she was watching with intense interest.
“Will Sinclair be a responsible broadcaster of the news,” she asked, “or a creator of the largest programmer of propaganda?”
Correction: August 14, 2017
A previous version of this article misstated the former role of Jill Geisler at WITI, the Tribune station in Milwaukee. She was a vice president of the station, not a general manager.