Kellyanne Conway: From Blueberry Princess to the architect of ‘alternative facts’

After watching Kellyanne Conway almost choke on her words before spitting out the phrase “alternative facts,” I suddenly – and to my horror – felt sympathy for this woman with degrees from Trinity College and George Washington Law School who has offered herself up as Trump’s apologist-in-chief.

What could compel a savvy, bigly successful businesswoman to put herself in such a position, I wondered. And so I decided to read up a bit on Conway, hoping to achieve some understanding of her motivations.

Conway was born Kellyanne Fitzgerald to middle-class parents in Camden, N.J. She grew up in Waterford Township, a small New Jersey community that recorded a population of about 11,000 in the last census. Her father, owner of a trucking company, divorced her mother when Conway was still a preschooler, and went on to marry three more times. Her mom worked at a casino in Atlantic City, supervising the chip cashing department. She and her daughter lived with her mother and two sisters. It was a staunch Catholic household, one that schooled Conway in the anti-abortion agenda that seems to guide her allegiances.

In her teenage years, she attended a private Catholic high school, where she was on the cheerleading squad, and worked at a blueberry farm, blueberries being a predominant crop in that area. In 1982, at the age of 16, she won the title of New Jersey Blueberry Princess. She worked packing blueberries for eight summers and, five years after her glory as Blueberry Princess, she participated in a blueberry packing competition. She tied for first place, and then asked for a recount, which resulted in her receiving the title of World’s Best Blueberry Packer.

In short, Conway was pretty competitive even then. Most girls would have been happy to share the title of World’s Best Blueberry Packer, but not Conway. She wanted to win.

During those idyllic years on the blueberry farm and skipping through the halls of her parochial high school, Conway rarely saw her dad. After the divorce, he disappeared from her life, and she did not encounter him again until she was 12.

Still, she was bright and she was driven, and her personal troubles did not interfere with her education. She graduated magna cum laude with a political science degree from Trinity and later was selected for the Phi Beta Kappa honor society. She graduated from George Washington with honors, and in 1995, when she was 28, she founded The Polling Co., which counted Newt Gingrich, Dan Quayle and the NRA among its clients.

Her polls were aimed at finding out what appealed to women – how to get them to like a congressman who opined that women should not be allowed into combat because they were more prone to infections than men; how to get them to take seriously a vice president who had criticized Candice Bergen for portraying a single mother on television; and how to get them to appreciate the advantages an AR-15 might bring to their households. The Polling Co. was the business that, 21 years later, earned her admittance into Trump World.

She first became passionate about politics, and the Republican Party in particular, when she saw Ronald Reagan deliver his nomination acceptance speech at the Republican National Convention. In an October interview with Ryan Lizza of The New Yorker, she stated that she was inspired by his “uplifting, aspirational, yet tough-guy thing.”

During the 1990s, Conway also became a popular pundit, usually representing the conservative woman’s point of view. She appeared regularly on comic Bill Maher’s Politically Incorrect, and in her interview with Lizza said that Maher, unlike the congressmen she often dealt with, was “a perfect gentleman.”

Of course, if you followed the early months of the 2016 campaign, when the Republican Party was trying to sort through 16 potential candidates for the presidency, you might remember that Conway was not always a Trump supporter. She co-chaired Keep the Promise, a Ted Cruz PAC that sponsored ads critical of Trump.

She slammed Trump for not being a true conservative and as “not willing to put in the work” needed for a successful campaign that could appeal to women. She took particular exception to Trump’s statement that women who seek abortions should be punished, arguing that the conventional view in the anti-abortion movement is that women who seek abortions are victims, not criminals. She stated that Trump needed to be more “transparent” about his tax returns. Perhaps most surprising, Conway was in favor of immigration reform. She once co-authored a document for the pro-immigration group FWD.us, founded by Mark Zuckerberg, and supported a path to legal status for undocumented workers.

So how did Conway end up in Trump’s camp?

How did she get from nice Catholic girl to counselor for a president who has been embroiled in multiple scandals with women, is currently working on his third marriage, and has publicly dissed the Pope by calling him a pawn of the Mexican government and the Islamic State group? How did a middle-class kid become a champion for a billionaire who has admitted to not paying federal income taxes for years? How did the World’s Best Blueberry Packer and supporter of gentle immigration policies end up as spokesperson for a guy whose most popular campaign promise was to deport millions of undocumented immigrants, many of them farmworkers?

Well, for one thing, Conway and her husband, George T. Conway, owned a condominium in Trump World Tower in Manhattan, and she served on the condo board. Trump sometimes came to the board meetings, and they developed a casual friendship during those years. She is also close friends with Rebekah Mercer, whose father, Robert, is a major supporter of Breitbart. When Trump wanted to hire Breitbart founder Steve Bannon for his campaign, Bannon told Trump he wanted Kellyanne Conway on the team, too. And, of course, Conway is no longer a middle-class kid: She and her husband own a $6,000,000 home in Alpine, N.J., one of the wealthiest enclaves in the nation.

Then there are the Clintons, a couple long reviled by Conway and her husband. During the Clinton presidency, George belonged to a conservative organization that instigated several legal challenges against the administration. In 1994 when Paula Jones filed a sexual harassment lawsuit naming Bill Clinton as the defendant, George wrote the brief.

After Trump’s first debate against Clinton, Conway appeared before the cameras to attempt to spin his dismal performance as a win. In her statement to the press, she mentioned that Trump had shown remarkable restraint in not bringing up Bill Clinton’s past infidelities during the debate – the statement, of course, allowed her to remind everyone of the affairs her boss so graciously declined to mention.

So this is the Conway I found.

After trying to penetrate her veneer and figure out who she might actually be, I have to say that I am still puzzled. Clearly, her Catholicism and anti-abortion stance are important forces in her life, but beyond that it’s impossible to tell where her loyalties really lie.

I am left with the conclusion that she might be exactly be what she appears to be – a cynic with few lasting fealties, a political hack who can easily abandon her principles to advance her career, a person who can look right at a camera and deliver the phrase “alternative facts” with dead seriousness, even though she might gag a tiny bit as she says it.

This story was originally published January 26, 2017 at 3:16 PM with the headline "Kellyanne Conway: From Blueberry Princess to the architect of ‘alternative facts’."