From Pound Ridge To Pennsylvania Ave—and Back

Since leaving the White House in 2003, former presidential press secretary Ari Fleischer has continued to thrive on politics, sports, family, and his beloved Westchester hometown.

Since leaving the White House in 2003, former presidential press secretary Ari Fleischer has continued to thrive on politics, sports, family, and his beloved Westchester hometown.

Not long after Ari Fleischer started working at the White House as President George W. Bush’s press secretary, he had one of those stop-and-smell-the-roses moments—not all that far from The Rose Garden. In March 2001, one of President Bush’s personal aides left Fleischer a note asking if he would like to join the president for a catch on the South Lawn.

The president, once a part-owner of the Texas Rangers, needed some practice before tossing out the opening-day first pitch at a Milwaukee Brewers game—and Fleischer, who always kept his glove handy in his trunk, was called into service.

It was time to play ball… at 1600 Pennsylvania Avenue.

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“It was one of those pinch-me moments: ‘I can’t believe I’m playing catch with the president,’” Fleischer recalls.

Looking around today in the Bedford office of Fleischer’s communications firm—and at his Pound Ridge home, too—there is enough memorabilia to fill the West Wing. There’s history big, small, and personal at every turn. Not just any old run-of-the-mill museum artifacts, but pieces from America’s great pastimes: sports and politics, both of which are important threads in Fleischer’s life.

In addition to a photo of Fleischer and Bush tossing a baseball, captioned, “With gratitude for catching the curve balls,” there’s a series of photos taken aboard Air Force One, and at several military bases scattered across the US on September 11, 2001,  when it was believed to be unsafe to return to Washington.

Across from his desk, there’s an image of Fleischer speaking with Pope John Paul II, of whom he says, “You instantly know you are in a special place with a special person.” Peppered throughout are photo ops with world leaders, menus of state dinners, a framed Navy Seals pin given to him by a friend, and scores of sports memorabilia, including signed jerseys from slugger Mark McGwire (whom Fleischer advised during McGwire’s return to baseball, as a batting coach, after his steroid scandal) and a bat from Cal Ripken Jr. that references those “damn Yankees.”

What makes each memory more fascinating than the one before is hearing Fleischer share personal stories and the behind-the-scenes accounts of a history he not only experienced but in some cases shaped and shared with the American people.

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A Witness to History

As President Bush’s press secretary from 2001 to 2003, Fleischer served as the commander-in-chief’s chief spokesman, a go-to confidant and advisor. He traveled the globe, met world leaders and sat in daily meetings with high-level figures, including Condoleezza Rice, Karl Rove, and Donald Rumsfeld. He was tasked with anticipating what the media was going to ask during three daily press briefings—and not flubbing the answers.

In political circles, being the voice of a president and facing off with some of the sharpest members of the Fourth Estate is considered a nearly impossible job, worthy of the sort of acclaim one might get from sparring with a gaggle of prizefighters—all at once.

Fleischer at home with Kitty, the Samoyed that rounds out the family. | Photo by Stefan Radtke

Fleischer stood at the press-secretary podium during what is one of the more interesting and controversial periods in modern American history: a presidency that was arguably decided by the Supreme Court, invasions of Iraq and Afghanistan, bad intelligence on Saddam Hussein’s WMDs, Anthrax scares, and, perhaps most defining, the 9/11 terrorist attacks, which killed nearly 3,000 people and set off a “war on terror” that is still being fought 15 years later.

“My job was to be the voice of absolute, unvarnished reality of how a very aggressive press corps would see things,” Fleischer says of his role at the White House. “Sometimes it made me a skunk at the picnic; other times it made me the person [Bush and other high-ranking officials] asked: ‘What do you think? How will this play?’ It always made for a better process.”

Many creative adjectives were flung at Fleischer as chief spokesman for the president, particularly from critics in the press corps, but friends and foes generally viewed him as measured, polished, even-handed, and unwaveringly loyal. Despite some frustrations with the press and what he sees as biases in coverage, Fleischer maintains that the United States is a better country for the free flow of information and crucial reportage done on a daily basis.

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At three daily White House press briefings, Fleischer was charged with doling out answers to the nation’s top journalists.

He personally liked and respected many reporters, even if it was their job to give him hell on a daily basis.But Fleischer’s White House days weren’t only productive on a professional level. It was there he met his wife, Becki Davis, an Indiana native who was working for the White House’s Office of Management and Budget. He remembers seeing her for the first time, chatting with a colleague, and knowing he had to meet her. Fleischer served up a first date on the White House tennis courts,—“I had to pull out all the stops,” Fleischer says—and they carved out a courtship in the fleeting free time they had. They were engaged a year later.

They got married in 2002 in an interfaith service (Fleischer is Jewish; Davis is Catholic; they are raising their children Jewish) that made its share of headlines if for no other reason than one of Washington’s most eligible bachelors was off the dating block. The Fleischers now have two children: daughter Liz, 11, and son Asa, 9. Their nuclear family is rounded out with Kitty, a 1½-year-old Samoyed, whose name reflects a bipartisan compromise because some family members wanted a cat. Becki, a nonprofit consultant who was New York co-chair for Carly Fiorina for President, is active with Westchester nonprofits and tours locally with Lawless, a cover band in which she plays guitar. In a 2003 People magazine article, Fleischer said his wife was the best gift that President Bush ever gave him.

While Fleischer clearly cherishes his time at the White House and serving President Bush, that alone doesn’t define him. It’s a solid chapter in a story that he’s still writing.

“My children, my wife, my family—that’s what defines me. That’s why I’m home,” Fleischer says of moving back to his childhood home of Pound Ridge more than a decade ago, after 21 years in the nation’s capital. “There just comes a time when you have to get off the racehorse and slow down and settle down. I found that time.”

Fleischer, 55, may have slowed down, but by any normal standards his horse is still running, even if it’s a fast trot when compared with his full-gallop days at the White House.

In political circles, being the voice of a president and facing off with some of the sharpest members of the Fourth Estate is considered a nearly impossible job, the sort of acclaim one might get from sparring with a gaggle of prizefighters — all at once.

Fleischer has been busy. In 2005, he wrote a New York Times bestselling memoir, Taking Heat, which gives readers an insider’s look at the press room and its machinations. Two years earlier, he started Ari Fleischer Communications—a company that offers media management, strategy, advice, and training to sports organizations and corporations—and he remains a regular on CNN, Fox, and MSNBC, speaking candidly about politics, which he says is fun because he can simply “let it rip.”

“I find it really refreshing to weigh in on what the candidates are doing,” he says. “It’s a lot more enjoyable.”

That’s another reason why @AriFleischer is active on Twitter, offering forthright insights and commentary, especially during the presidential debates. In recent years, he has relived the events of 9/11 on its anniversary, sharing photos and recalling, tweet-by-tweet, what it was like to be by the president’s side when the country was under attack. He relies on the copious notes he took that day (the originals are locked in a vault in Northern Westchester), saying that despite the intense pressure and stress of that period, it was imperative that everybody did their job.

Somehow Fleischer still finds time to play baseball—not the slow-pitch, beer-guzzling version of softball but the hard-throwing, wooden-bat-swinging, Charlie Hustle brand of ball—in a league for men who love the game and aren’t betting that the Yankees, or even the Bridgeport Bluefish, are gonna come calling.“It’s a bunch of old men who know we’re old and love to play,” he says.

Fleischer served as President George W. Bush’s press secretary from 2001 to 2003, through memorable historic moments including the 9/11 terrorist attacks, invasions of Iraq and Afghanistan, and Anthrax scares.

When Fleischer speaks, his passion for sports is obvious—as is his love for his family, his faith, and his hometown, which he says hasn’t changed all that much since he was a child. During his days at the White House, his walls weren’t full of pictures or mementos of Washington but of his hometown: old portraits of the village courthouse, storefronts, and historic maps of Bedford and Pound Ridge (“just to remind me that this is who I am”) and of the place he would one day return. He recalls thinking as a young boy how great it would be to open a business on the main drag in Bedford. Now, with his eponymous communications company, he has achieved just that.

“It’s the same rural, small-town feel with friendly people,” he says as he gazes out the window of his office. “I still drive past the stone walls and old barns and say to myself how lucky I am and what a beautiful area this is.

“There’s just something magical about this area that always drew me home,” Fleischer adds. “It’s friendly, it’s cozy, it’s beautiful, it has open space. There’s a comfort to being here that I’ve always cherished.”

That’s precisely why he’s raising his own children there now. Fleischer has a typical suburban existence, actually. He likes spending time with his kids, attending their sporting events and school activities, and visiting area parks and restaurants. His parents live in nearby New Canaan, which keeps them a tightly knit group.

In winter, the Fleischers ski most weekends at Windham in the Catskills. The spring and summer are all about sports for Asa, while Liz is involved in shows and other activities. Between games, practice, and summer camps, the Fleischers enjoy entertaining family and friends, and make great use of their pool, which features a winding and wicked slide that is just as popular for the grownups as it is for the kids.

Fleischer says he and Becki have settled down well in the ’burbs, and enjoy raising their kids together. They are both active and old-fashioned parents. They stress independence, but have rules they expect their children to follow. “Washington is full of children,” Fleischer jokes. “But my children behave. They don’t get away with much.”

Related: Our April Issue

Raised on Sports & Politics

His proclivity for sports and politics were apparent early on. A two-time class president at Fox Lane High School in Bedford, Fleischer also competed with the gymnastics and baseball teams. Former athletic director Rod Mergardt, who was Fleischer’s gymnastics coach for three years, says communications and teamwork were always Fleischer’s forte.

“He would probably tell you that he was not the best gymnast and that would be the truth, but he worked his tail off,” says Mergardt. “He was a goal setter. He was the kind who everybody wanted to have on the team.”

While winning a gold on the parallel bars was as unlikely as playing shortstop for his beloved Yankees, it was evident that big things were on the horizon, Mergardt recalls, because Fleischer was smart, focused, and driven as a teenager.

Fleischer grew up in a politically active family, the youngest of three boys. His parents, Martha and Alan Fleischer, had little Ari stuffing envelopes for the Pound Ridge Democrats. He was raised a liberal Democrat, and, in third grade, supported Robert Kennedy for President. While working for Bush 43, his parents often joked about Fleischer’s Republican allegiances, saying it was a “phase he would grow out of”; clearly, they have a good sense of humor.

When he started at Vermont’s Middlebury College in 1978, Fleischer began his academic career as a full-fledged lefty. But the political-science major who minored in French slowly began to shift to the right, in part because he didn’t like what he was seeing in the post-Vietnam and Watergate era—protests, no American flags on campus, and lackluster pride in the US. It just wasn’t right, Fleischer felt.

Fleischer with his wife, Becki, and their children, Liz, 11, and Asa, 9, at their Pound Ridge home.

Furthermore, Jimmy Carter’s foreign policy made him question Democratic views, and Ronald Reagan’s “peace through strength” brand of governance drew him toward Republican thinking. By the time he graduated in 1982, he identified as a Conservative Democrat.

It was upon his return to Westchester that his shift to the right was solidified: As an intern for the Westchester County Board of Legislators (under then-Republican chairman Andrew O’Rourke), Fleischer, still a registered Democrat, witnessed politics at play. The Democrats, who assumed Fleischer was a Republican, made a fuss over his hiring, claiming it was partisan.

“It struck me that the Democrats objected to my hiring without ever asking who I was and whether I was a good worker,” Fleischer says. “It left a bad taste that they would challenge my work ethic and integrity.”

From there, he worked on his first congressional campaign, in Westchester, serving as press secretary to Jon Fossel, a Republican New York assemblyman who ran unsuccessfully for congress (proof, Fleischer jokes, of the low bar of entry for press secretaries on the campaign trail). By then he’d fully embraced the GOP: Fleischer finished out the race, switched parties, and moved to Washington, sleeping on his oldest brother’s couch for months.

While in the Beltway, Fleischer landed a job as press secretary for Long Island Congressman Norman Lent, served as field director for the National Republican Congressional Committee and for a short time worked with Westchester Congressman Joseph DioGuardi, a Republican who was unseated in 1988 by Representative Nita Lowey, who still holds the seat. After that loss, Fleischer spent many years as spokesman for Senator Pete Domenici of New Mexico and later for the House Committee on Ways and Means, where he learned a lot about public policy. He later worked as communications director for Elizabeth Dole’s presidential campaign, a job he landed with the help of a Westchester colleague. After Dole left the race in 1999, the Bush campaign drafted Fleischer. He was one of the few New Yorkers working in a campaign loaded with Texans. Bush affectionately dubbed him “Ari-Bob.”

Having spent so much time in Washington, Fleischer found himself drawn to Southern politics. He was turned off by the yelling and table-pounding of those like his native state’s US senator, Alfonse D’Amato, and others, deciding that it was the subtle ways and charm of Southern pols that proved most effective. They would “run circles around people,” he says with an ever-so-slight Southern drawl.

Through it all, Fleischer learned there was an art and subtlety to politics. Being successful during a briefing with the press required a combination of substance and showmanship; the best press comes from mastering both, he says.

“My children, my wife, my family—that’s what defines me. That’s why I’m home. There just comes a time when you have to get off the race horse and slow down and settle down. I found that time.”

Today, Fleischer puts his lifetime of political lessons learned into his Bedford-based business. The company has a small-town charm about it, but he and his staff work with large corporations, sports leagues, coaches, and premier athletes. Tapping his decades of experience, he teaches clients how to speak with the media, deal with crises and put their best feet forward. Some of his current and former big-name clients include IBM, MLB, NFL, NBA, US Olympic Committee, and the College Football Playoff, to name a few.

Another high-profile individual client is reigning Super Bowl champion and future first-ballot Hall of Famer Peyton Manning, the former Denver Broncos QB who in the midst of the 2015-16 season had fought allegations that he used performance-enhancing drugs.

Fleischer says the tribulations that corporate leaders, sports leagues, and athletes go through are remarkably like those in elected office. “Politics teaches you how to communicate in a crisis or in a pinch and how to do it well. If you don’t, you lose your re-election,” he says. “The crises [I deal with] now aren’t life and death or war and peace, but for my clients, they are massive events. I get a lot of satisfaction if I can get them through it.”

Though the company was founded in 2003, the firm first took hold when political junkie Sandy Montag, president and CEO of The Montag Group in White Plains, noticed that Fleischer would often make sports references during his daily briefings at the White House. Montag, whose sports-marketing and consulting company manages a slew of big-name broadcasters and coaches, notably football color-commentator John Madden, NBC sportscaster Bob Costas, former Giants head coach Tom Coughlin, and local CBS anchor Mary Calvi, boldly cold-called the White House in 2003, thinking there might be a way the two could work together. They spoke, hit it off, and, a year later, the two were business partners. “With Ari, it’s not just a passion for sports; it’s a knowledge of sports,” Montag says. “He loves being in sports. He’s a kid in a candy store.”

Not only do players and superstars respect Fleischer, Montag notes, but he works with the highest level of executives—commissioners, team owners, and networks. “He commands respect in the sports world,” Montag says.

For a guy who could have written his ticket—a very lucrative one—as a Washington lobbyist or set up shop anywhere in the world, it’s telling that he returned home and remains so accessible, says Westchester County Executive Rob Astorino, who met Fleischer in 2005 during his first unsuccessful run for the post he currently holds. The two immediately hit it off, not just as Republicans but as Miami Dolphins fans.

In the subsequent years—during Astorino’s 2009 run for county executive and his 2014 run for governor—Fleischer was helpful on a number of fronts: on issues of the economy and jobs and what was on voters’ minds.

“He gave me the good, the bad, and the ugly about what it’s like,” Astorino says of Fleischer’s advice about running in a high-stakes, high-cost race for New York State governor. “It was exactly what I wanted. A lot of people will tell you what you want to hear, when what you really want is to hear the unvarnished truth.”

But what Astorino remains most impressed with regarding Fleischer is that despite his success, he is so well-grounded.

“The best thing I can say about Ari is that, despite how important a position he’d had, he’s still one of the most down-to-earth people,” Astorino says. “He never forgot his roots or what is important.”

Ari’s Thoughts on the 2016 Election

This is one of those unique times in American history when “politics is on the hinge” and people want change, says Ari Fleischer, who has been on the inside of his share of campaigns.

The electorate is fed up. Promises made. Promises broken. Gridlock. Stagnant wages. Uncertainty. A shrinking middle class. It’s a narrative that is playing out among voters across the country and is shaking up the 2016 presidential race. “It’s not hard to understand why people are frustrated,” he says. “There’s a real rejection of all things Washington and establishment.”

How else can you explain the rise of real estate reality star Donald Trump and Democratic Socialist Bernie Sanders, and a crowded Republican field that started with 17 candidates? People are willing to take their chances on an outsider, and “Trump has seized that,” Fleischer says.

While Fleischer gives Trump a better than 75-percent chance of landing the nomination, he doesn’t necessarily view him as a Republican, but rather an independent renting the GOP because it suits his interests. For the Dems, he thinks Hillary Clinton has the nomination locked up.

His advice to naysayers and Dems that want to take on Trump: “Get ready. The wrecking ball that swung through the Republican party is headed to the Democratic party. There hasn’t been a ceiling set yet for Donald Trump that he hasn’t busted through.”

What could happen, especially if Trump wins, is that the two major parties will remain, but the electorate will consist of three major ideological blocks: Liberals, Conservatives, and populists, with the latter being the most amorphous.

But Fleischer sees no need to fret. He believes the nation will survive a Trump presidency— just as it will endure a Sanders, Clinton, Rubio, or Cruz presidency—for the same reasons it has survived President Barack Obama’s tenure in the White House.

“I will always have tremendous faith in this country because of the Constitution,” Fleischer says. “Our system, with a series of checks and balances, makes it hard to get things done. But it keeps us free and protects us. This country will always survive and thrive so long as the private sector remains bigger and more important than the government sector.”

Jerry McKinstry is managing director of The November Team, a political strategy and communications firm based in Westchester. Prior to working in public relations, he was a political correspondent with the Journal News and a member  of Newsday’s editorial board. 

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