There was a time when the National Rifle Association was known primarily for promoting gun safety and advocating for gun ownership for hunting and home protection.But that seems a long time ago. It still does those things, to be sure, but these days the NRA is far more recognizable as an uncompromising political force, aggressively defending its interpretation of the 2nd Amendment, while working to defeat any and all politicians it views as its enemy. It's a transition that took place over several decades, but one race in the 1990s in the northeast corner of Oklahoma can be seen as an early indication of the direction the NRA would take. Rep. Mike Synar, D-Okla., experienced NRA support early in his career, only to have the organization work against him as his views on guns shifted. Synar, a Democrat from Muskogee, was just 28 years old when he went to Washington. Yes, Oklahoma still sent Democrats to Congress back then — in fact in 1978, the year he was elected, Democrats held five of the state's six congressional seats. Oklahoma, the home of legendary folk singer Woody Guthrie, still had a deep populist strain in its politics. That has long faded, however, as the state's entire congressional delegation today is Republican and very conservative. In those early years after his election, Synar actually counted the NRA among his supporters.The archives at the University of Oklahoma, where Synar's papers are housed, include a black-and-white photograph of him meeting with Neal Knox, executive director of the National Rifle Association's lobbying arm, in 1981. There's also a 1980 letter from Knox to the NRA membership that states, "The National Rifle Association's political victory fund is pleased to announce its endorsement of Congressman Mike Synar for reelection from Oklahoma's 2nd District."But the honeymoon did not last.After the assassination attempt on President Ronald Reagan in 1981, as well as several mass shootings in the U.S., Synar began to support the call for stricter gun laws, including the Brady Bill, which was named after James Brady, the presidential press secretary wounded in the attempt on Reagan's life. Speaking on the floor of the House of Representatives in 1993, Synar said that since the Brady Bill had been introduced, "Six long, murderous years have passed; 100,000 of our best and brightest citizens have been killed by handguns." It was strong language, but it reflected Synar's beliefs. An avid hunter, he felt that certain regulations and safeguards such as the five-day waiting period for handgun purchases and background checks were warranted. He would also join his colleague in the House, then-Rep. Chuck Schumer, D-N.Y., in co-sponsoring a ban on assault weapons. Needless to say, the NRA was not pleased.The organization responded by pouring cash and energy into defeating Synar, including supporting Democrats to challenge him in primary elections. In the 1992 primary, his Democratic opponent was supported by a series of full-page newspaper advertisements in daily papers in the districts largest cities.One such ad, in the Tulsa World featured rows of banner headlines that labeled Mike Synar "Anti-HUNTER" and "Anti-GUN" and "Anti-OKLAHOMA." It ended by saying it's time for voters to become "Anti-SYNAR." Then there's the call to action in a black box at the bottom: "VOTE DREW EDMONDSON SEPTEMBER 15.Edmondson would force Synar into a runoff election, which Synar would eventually win on the way to capturing another term in the general election. But it was a close call, and Synar was on notice.Synar sought his ninth term in Congress in 1994 and faced another Democratic primary challenge. This time it wasn't just the NRA, but other interest groups who'd joined in the effort to defeat him, including cattle ranchers and oil and gas interests. Oklahoma was an increasingly conservative place, and Synar's progressive politics were increasingly attracting opposition. But the NRA worked hard to increase its membership in the district. It succeeded at that and at getting voters to turn out. It's a strategy the organization has only gotten better at over the years. On primary night, Synar was forced into a runoff against a political newcomer, retired middle school principal Virgil Cooper. Cooper would win the runoff by a narrow margin, ending Synar's political career. Cooper then went on to lose the general election to Republican Tom Coburn, who would go on to a lengthy career in the U.S. House and eventually the U.S. Senate.Gene Wallace, who worked for Synar in those years as his congressional district manager in Oklahoma, says they didn't fully appreciate that Synar's votes on gun control would hurt him."We did dismiss it," the Wallace says, "because it wasn't part of the public square debate. There wasn't anybody calling our office or ... coming to our office and saying, 'Hey, we're fearful that someone's gonna take our guns.' "Looking back 23 years to that primary election night in 1994, the 74-year-old recalls what the congressman said to him in defeat, "He said, 'You know, things change, and the pundits will figure this out in the future. But there's not a decision I made and a vote that I made that I regret.' "The NRA declined a request for comment on this congressional race.As for Synar, his story took a tragic turn shortly after losing that election.The following summer he began having vision problems. Doctors suspected something serious, and detected brain tumors. The cancer would claim his life in January 1996. He was 45 years old. Among those speaking at a memorial service in Washington, D.C., was Synar's longtime friend then-President Bill Clinton. In his remarks, an emotional Clinton reflected on their friendship — Clinton being Oklahoma's neighboring state of Arkansas. He then noted, "If I hadn't been elected president, he never would have had to vote on that assault weapons ban."Clinton also said of Synar, "He always had that wonderful saying, you know, 'If you don't want to fight fires, don't be a fireman. If you don't want to cast votes, don't be a congressman.' "In the decades since those contests some quarter of a century ago, the NRA has escalated its political activity. It wins by painting its opponents as out of touch with the values of their district. In 1994, Synar was among the first to learn that. Editor's note: The clip of a campaign ad used in the audio version of this story is courtesy of the Political Communications Center at the University of Oklahoma. Copyright 2017 NPR. To see more, visit http://www.npr.org/.