In 1999, Monticello High School sophomore Chase Cushman was a member of the first group of students to walk through the doors of the brand new Monticello High School.
Fourteen years later, Cushman earned another, slightly more prestigious, first, when he became the first Monticello graduate to hold a director position in the White House, serving as the Director of Scheduling for President Barack Obama and eventually as the Director of Scheduling and Advance.
It was a career and life path that started in Monticello, ventured through Collegeville, took a pit stop on a losing congressional campaign in Minnesota, and then veered toward the campaign of a young senator in Illinois. That became a presidential campaign, which turned into a presidency. Cushman’s position went from volunteer to campaign position to the low rungs of the White House to a director position that met daily with White House department heads and worked directly with President Obama.
“It was an interesting ride,” said Cushman, with a laugh.
The uniqueness and “cool factor” of Cushman’s positions at the highest level of United States government are not lost on him.
“My job was really kind of interesting because I was one of the few people in the White House that had insight through all of the silos,” said Cushman. “My job was to be the person that had a 30,000 foot view of all the things that the president was touching so that everyone knew how their stuff was going to affect somebody else’s thing.”
Cushman also noted that he firmly believed his local upbringing helped him both to become the person he is and to reach the positions he did.
“I think about my holistic upbringing a lot as part of the reason why I got to where I was. Look, you have to be able to work hard, be patient, and know when to speak your mind and when not to,” said Cushman. “I think these are kind of values we have in Monticello.”
Cushman was especially tied to the district, thanks to a father, Mark Cushman, that spent decades teaching at Monticello High School.
Chase said he both enjoyed and valued his time in the school district and that it certainly played a role in aiding his future success.
“I had very good History and English teachers that reminded me it’s about understanding the context of what you’re discussing,” said Cushman, noting that especially in politics, if you don’t understand the context of a discussion, or know how to frame your argument, you’ve already lost.
After graduating from Monticello in 2002, Cushman headed to Collegeville to attend St. John’s University. It was there that he started speeding down the path toward politics.
“I went to school thinking I was going to be a history teacher,” he said. “But I took one political science course and kind of fell in love with the notion of politics.”
Prior to his senior year, Cushman spent a summer interning in Washington DC. He wouldn’t look back from there.
“That kind of got me hooked,” he says now.
Following graduation from St. John’s, Cushman found a position working on Patty Wetterling’s campaign in 2006. When she lost the race to Michele Bachmann, Cushman turned his focus to finding a position on Capitol Hill in DC, something he’d been eying since his internship.
With his life seemingly made up of constant flights back and forth to the nation’s capital, a friend that Cushman made on the Wetterling campaign invited him to come stay with him in Chicago for a short time. The friend’s apartment had easy access to O’Hare Airport and provided a change of scenery for Cushman. Soon it would provide much more.
That friend happened to grab a job in the exploratory stages of a presidential campaign for then Senator Barack Obama. A few weeks after Cushman had moved in, Obama publicly announced his candidacy. At that time, Cushman’s friend suggested he start coming in to volunteer for the campaign, which had a dire need, while he was in between trips to DC.
Within two weeks, Cushman had received a job offer from Obama’s campaign folks, as they tried to build out their staff for the campaign that was starting to heat up.
Right about the same time, Cushman got a call from Capitol Hill, offering him a congressional office job that he had long been seeking.
“It was just one of those moments,” said Cushman, who gave it a little thought, but didn’t need a lot, before deciding he would stay in Chicago and work on the campaign for Obama, who at the time was still considered a long shot.
“I called the Capitol Hill office back to let them know,” said Cushman. “They said, ‘are you sure? Do you want to take a minute to think about this?”
It was suggested that with Hillary likely to get the party nomination, there was a good chance the Obama campaign would soon come to an end.
Cushman said all that did was get his competitive spirit up, and solidify his decision.
Months later, his decision paid off in a major way. Obama would win the Democratic nomination and then the Presidential election. When campaign staff approached Cushman about a job at the White House, he asked to be placed in scheduling. He’d been doing advance work for the campaign, and was looking for a little less travel and a change of pace. His wish was granted and he became one of three schedulers for President Obama.
During the next eight years, Cushman worked his way up the rungs of the White House, becoming a Senior Scheduler in 2012, the Deputy Director of Scheduling in August of 2013, the Scheduling Director in February 2014, then finally the Scheduling and Advance Director in December of 2014. Through it all, he got a chance to learn the inner workings of the most powerful office in the world, to work directly with the 44th President of the United States, and to do a whole lot of really neat things.
However, at the midpoint of his time in the White House, he wasn’t sure it would be an eight-year position.
“The thing about the White House is you plateau pretty quickly. The White House has got a lot of department heads and a lot of staff assistants. In between, there aren’t a lot of middle rungs,” said Cushman. “I’d kind of hit the ceiling. I really liked my job. It was a really cool job. But I kind of felt like, I’ve been doing it for four years, and where else is there to go from here?”
Several conversations with those around him helped change the outlook. He was encouraged by current and past directors that he would likely have several upcoming chances at upward mobility, due in large part to his strong relationships with both staff and the president, if he stayed with it.
That was enough to drive Cushman to keep going.
“It was partly because they asked, and partly because I just really liked the people I worked with,” said Cushman. “It was a hard job, but it was easy because I really enjoyed everyone I worked with.”
The decision would pay off with several promotions in the next two years, eventually leading to him taking charge of the entire scheduling and advance department.
Cushman explained his department, and his director position, as such: “There are kind of two wings to our operation, one is the scheduling side and one is the advance side. The advance side are kind of the executors. They’re the folks that go out in front of him and really figure out how that all happens. The scheduling folks figure out what does he all do. We’re making sure that everyone who has an equity in what he’s doing are talking to each other and driving them towards decisions. My job was to one link both sides of our operation ... and my job as the director was to really be the person that worked with senior staff on figuring out what to do with the president’s time. So I spent most of my day sitting in meetings with other department heads, so that my staff could actually do their jobs, which was executing the president’s schedule.”
As a director, Cushman said he met with the President weekly, and more often in advance of foreign trips. He also traveled on all foreign trips and met daily with the President when abroad.
The foreign trips were certainly one of the highlights of the position. Cushman said his favorite city was Seoul, South Korea.
“It has got this old kind of ancient feel, similar to being in China. But at the same time they’ve modernized real recently so it’s built up like Japan,” he said. “The food is good, the people are good ... it’s one of the coolest places you’ll visit if you ever get a chance to.”
He also had fond memories of trips to Israel and Jordan (“Phenomenal places, especially for a history buff like me,”).
Spending so much time with the President both in work environments and traveling environments afforded Cushman a unique insight into his person. And he has only good things to say.
“This is going to sound like something you’re supposed to say, but he was a good boss,” said Cushman. “He was always the calmest man in the room, and he was very kind.”
Cushman also appreciated just how much of a family man Obama was. Shortly before Cushman’s wife Ashley gave birth to their first child, a now two year old girl, the White House had instituted a paternity leave policy that allowed fathers to take as much time off as mothers.
Cushman, brand new to his position of Director of Scheduling and Advance, was hesitant to use much time at all.
“He pulled me aside and said look, the White House thing is fleeting, but your family is something that you’re always going to have. So you need to take this time,” said Cushman.
Obama also gave Cushman a slight ego check and told him the place would run OK without him, before adding that it was important that he took this time so that other fathers could see it was not only OK but encouraged.
“He said fatherhood was the most important thing I was going to do, and my job was secondary to that,” said Cushman. “Coming from the president, I’ll never forget that.”
One other trait that stood out to Cushman about the President was his memory.
Cushman’s first opportunity to work directly with him came when he was doing advance for the campaign. His job was to meet the motorcade in New Hampshire and to get the presidential candidate into a small conference room meeting with a couple of union leaders - not too big of a deal, thought Cushman.
“Well the motorcade pulls up, out he pops, we’re walking in, and I totally flat tired him [stepped on the back of his shoe]. I’m just like ‘oh god, this is terrible,’” said Cushman, who noted he was just 23 at the time and thought he had ended any budding career he may have.
“He was fine, he stood up and said ‘well, that didn’t go too well,” Cushman remembers, with a laugh.
Cushman never received the pink slip that he may have feared. However, he did get a reminder, more than a year later.
It was 2009, and Cushman was briefing the President for the first time.
“You could tell I was nervous,” said Cushman. “And he said ‘don’t worry, your briefing went a lot better than the first time I met you and you tripped me on the way into that meeting.”
“We had a good laugh about it,” said Cushman.
The position offered enough other highlights and memories to last a lifetime. One of Cushman’s favorite moments was meeting the pope when he visited the White House. The White House staff kept his place on the welcome delegation secret from him, one of the lone high-ranking Catholics in the office, until the morning of the visit.
“When the president introduced me to him, I shook his hand. Then when I was about to leave the room, I ran back and shook it again just to double dip, to get two hand shakes in,” said Cushman, retelling the story with infectious enthusiasm while also remembering how the rest of the staff laughed at him. “That was one of those times where I was like, this job is cool.”
Cushman said another highlight was being able to use the State Room, particularly for holiday parties in the White House.
“Our favorite time of the year there was Christmas party season,” he said. “Doing a Christmas party when you’re sitting in the state dining room, drinking amazing egg nog, and the fireplaces are going ... you feel like you kind of went back to a simpler time in America.”
Of course it wasn’t all parties and travel. The job came with the everyday stresses that all jobs come with, as well as the wear and tear that comes with an industry as divisive as politics.
Cushman said he certainly wasn’t immune to feeling that grind during his eight years in the White House. But he always found a way to keep it in perspective.
“The really cool thing about that building is you get to walk out that front gate when you leave and you look behind you and it’s the White House,” said Cushman. “Whenever I was getting down about it, I would sometimes just walk outside, walk out the gate and then walk back in again, just to remind you of where you were and what you’re doing.”
As far as the divisive nature, Cushman noted you certainly have to be able to let some things slide off your back. But if you’re in the industry for the right reasons, such as to work to better the lives of others (and he noted there is no where better to do than government, the largest entity in our nation), it all remains worth it.
And, he added, that the divisive nature at least indicates a democracy at work.
“Our democracy only works when people are involved. And you’re seeing a time where people are actually getting back involved again,” said Cushman. “And is it loud and is it noisy? Yes of course, but it’s supposed to be, that’s what democracy is. At least people are engaged right now, and people are paying attention, and people are not afraid to voice their opinion for what they care about. And is it cynical? Yes. But don’t let that cynicism dissuade you from feeling that our democracy is thriving - because it is.”
For eight years, Cushman earned the opportunity to work in the heart of that democratic process, alongside the President of the United States of America.
The 2002 MHS graduate, who is currently taking some time as a stay-at-home dad in Minneapolis, said he often reflects on where he came from, and where he’s been.
“I think about it on a regular basis, especially now that my life is a little slower,” said Cushman. “It makes you realize that our lives are just a series of choices. It’s not that any one is right or wrong, it’s just how you got here. It’s funny how you can have a plan for what you want to do, but sometimes that plan changes and you just kind of have to have the courage to go with how it’s changing on you.”
Cushman isn’t sure what’s next. He’s enjoying his time as a dad for now, with an eye on getting into the nonprofit sector, where he can continue to feel like he’s working on behalf of people. But regardless of where he goes from here, he already has stories, experiences, and memories to last a lifetime.
“It was an interesting ride,” he said. “I happened to make that one choice back in January of 2007 where I decided to kind of forgo the safe plan, the plan that I went to school for, that I wanted to do ... and join up with this guy named Barack Obama. And, here we are.”
