Ladies & Legends: Elaine Chao – Trailblazer and Historymaker
By Juyun Kim | 23 Jul, 2025

An abbreviated look at Elaine Chao’s (the first Asian American woman to serve in a President’s cabinet – ever!) rise to household-name status.

Join us as we explore the lives and times of some of history’s most prominent women of Asian and Asian American descent.

In this inaugural episode we look at Elaine Chao’s (the first Asian American woman to serve in a President’s cabinet – ever!) rise to household-name status.

“I have never forgotten what it feels like to be on the outside looking in. To feel that sense of vulnerability and fear that we’re not going to make it.” (Washington Post, 2019).

This is a quote from Elaine Chao former U.S. Secretary of Labor and U.S. Secretary of Transportation, who has built her legacy of quiet effectiveness through decades of professional achievement and public service. 

She is known for expanding the presence of the Peace Corps in Eastern Europe and Central Asia, rebranding the United Way as CEO after financial scandal, and being the longest serving Cabinet Member (and the first Asian American female cabinet member) under George W. Bush’s administration, serving all 8-years of his presidency. Her legacy is one of integrity, trust and vision.

"Hello welcome to Ladies and Legends, the podcast where we explore the personal journeys of legendary women and business leaders of Asian and Asian American descent. I’m your host Juyun, and today’s story is about a leader and legend in her own right, a Taiwanese American powerhouse who has traversed effortlessly between the worlds of finance, nonprofit leadership, and ultimately found herself at the highest levels of federal government as U.S. Secretary of Labor under former President George W. Bush and U.S. Secretary of Transportation under President Donald Trump.

She’s also the recipient of 38 honorary degrees recognizing her accomplishments and public service (what Asian parent wouldn’t love that?).

I’m talking about Elaine Chao—the first Asian American woman to serve in a U.S. President’s Cabinet. From her childhood as an immigrant to her leadership roles at the highest levels of U.S. government, her story is one of grit, ambition, empathy and strategic vision.

And she’s not the only high achiever in her family—wait till you hear what her sisters are doing. Let’s get into it."

PART 1: Childhood and Immigration Story 

"Elaine Chao was born on March 26, 1953, in Taipei, Taiwan, as the oldest of what would eventually become a family of 6 sisters. 

Her parents, James and Ruth Chao were a striking, but unlikely pairing. While her mother was from an affluent and distinguished family in the Anhui province, her father came from a small farming village of 10 families outside of Shanghai. 

But from his humble roots and early career as a merchant mariner, he would ultimately go on to become the founder of Foremost Maritime Corporation (currently, the Foremost Group, a privately held American shipping company whose revenue Zippia notes as $543 million in 2024).

The value of education and determination were foundational to Elaine’s DNA.

In fact, her father became one of the youngest ship captains in Taiwan at the age of 29, and he went on to take a national exam, across many areas, conducted over 4 days, once a year, in Taiwan. He scored #1 in the country and broke records due to his intelligence and athleticism. 

And with this success came newspaper articles and offers of scholarship funds, which allowed him to come to the U.S. – while he had many options, the perception of opportunity and meritocracy appealed to the ambitious young man.

Back to our heroine. 

The year was 1961 and Elaine was 8 years old, a girl with a knowing smile and short, full, curly black hair. The top songs on the music chart were doowap classics like “Runaround Sue,” “Runaway,” and “Will You Still Love Me.” 

And it was at this tender point in her development that she moved to the U.S. on not so posh accommodations on 37-day freight ship journey with her mom and two younger sisters. Her father was waiting for them Stateside. He had moved to New York 3 years earlier, sending money back home until his wife and daughters could join him.

Of the journey, Elaine has said, “It was a thirty-seven day ocean journey and I remember going through the Panama Canal. For an 8-year, it was great fun, but I can’t imagine the trepidation and the anxiety that must have frightened my mom, who was the only woman on board the ship with three young girls, children.”

James said of the family matriarch, Ruth, Elaine’s mom, “she kept an optimistic spirit,” through the stress and uncertainty around their big move.

And this resilience undoubtedly trickled down to Elaine and her sisters.

On her first day of 3rd grade, Elaine who was accompanied by her dad who took time off of work to come with her, bowed out of respect to her new teacher. She was met with peels of laughter from her classmates, and though she didn’t know any English, was proficient within a year.

 She credits her parents with creating a home full of encouragement, discipline, and a love of learning. While her father founded Foremost Group, her mother earned a master’s degree from St. John’s University, while raising Elaine and her sisters in a one bedroom apartment in Queens.

Elaine has said, “We were surrounded by love and by very secure parents, who really looked out for us, so we never felt any want.” 

And while they were the brunt of jokes for having a family of 6 daughters with many weddings to pay for, and no male heir to pass the business down to, their parents always instilled in them a deep sense of self worth.

The Chao family’s values—education, resilience, and service—ran deep. And those seeds would bear fruit not only in Elaine’s life, but in the lives of each of her sisters."

PART 2: Education and Career Launch 

Elaine attended Mount Holyoke College, majoring in economics. In the second semester of her junior year, she studied money and banking at Dartmouth College and she later earned her MBA from Harvard Business School in 1979.

Noting her leadership and collaborative strengths even then, her peers elected her to be Class Secretary and Class Marshall.

Elaine’s sister Angela, the late CEO of the Foremost Group has said, “My parents have always believed in the transformative power of education. There was this running theme in our family that you educated yourself to become productive members of society so that you had something to contribute back.”

While at Citicorp Elaine learned about the prestigious White House Fellowship Program and was ultimately selected as 1 of 12 White House Fellows during the Reagan Administration.

Shortly after, at the age of 33, she became the Deputy Administrator of the Maritime Administration in the U.S. Department of Transportation. Some of the goals of the Maritime Administration include improving port efficiency, maintaining shipbuilding and repair infrastructure. So the organization’s impact is both economic and indirectly supportive of naval development as well.

In 1989, as a natural continuation of her career trend in public service, then-President George H.W. Bush appointed her as Deputy Secretary of Transportation. And in 1991-1992 she was the director of the Peace Corps where she expanded the Peace Corps’ presence in Eastern Europe and Central Asia in countries like Poland, Latvia, Lithuania, Estonia, Ukraine, Georgia, Armenia and Russia.

And between the Bush administrations, from 1992-1996 Elaine served as President and CEO of the United Way, where she worked to repair a tattered brand image left by William Aramony, the former CEO of the United Way for more than 20-years who had been accused of using the organization’s funds to travel and gift lavishly. 

Under her leadership, United Way restored donor trust and accountability, proving her efficacy to stabilize large institutions. She went on to work for a conservative thinktank in Washington D.C. where she remained until her appointment as U.S. Secretary of Labor under George W. Bush.

This made her the first Asian American woman ever to serve in a U.S. Cabinet.

She’s said of her career, “When I entered the workforce there were not many women, nor many Asian Americans. So I have pretty much been the “first” in every job I’ve ever had. But being different has also given me a different perspective, an outsider perspective which makes me a more compassionate, empathetic, stronger leader.” (Women to Watch podcast interview)

Side note:  It was during this time that, according to the New York Times, Stuart Bloch, a liberal public interest lobbyist, and his wife Julia Chang, the U.S.’s first ambassador of Asian descent, invited Elaine and Senator Mitch McConnell to dinner.

In 1993 on Ronald Reagan’s birthday, not a coincidence, they were married in a chapel on Capital Hill.  Elaine wore a hot pink blazer dress, and Mitch wore a dark blue, pinstripe suit for the occasion. 

Elaine’s husband has said in a TIME article: “People remark that I’m in a mixed marriage. I don’t see it that way," "In my first marriage, I married a liberal. Now that was a mixed marriage. With Elaine, she and I understand one another."

This was an exciting time in Elaine’s life.

She stayed in her role as U.S. Secretary of Labor for all eight years—longer than any Labor Secretary since World War II. During her tenure, she focused on worker training, enhancing transparency in union finances, and workplace safety.

New milestones were achieved during her tenure, including record low worker injury, illness and fatality rates.

The department also updated Family and Leave Act regulations, spearheaded the Pension Protection Act, implemented the MINER Act and crafted new regulations to help energy workers and veterans.

Fast forward to 2017 when Elaine Chao made history again. President Donald Trump appointed her Secretary of Transportation, making her one of the few people to serve in the Cabinet under two different presidents.

In that role she oversaw modernization efforts across infrastructure, introduced guidelines for autonomous vehicles and drones, and pushed for deregulation in transportation.

But her time in the Trump administration ended dramatically. After the January 6th Capitol attack in 2021, Chao became the first Cabinet member to resign in protest. Her resignation letter cited the 'deeply troubling and entirely avoidable event' that unfolded at the Capitol.

That moment spoke volumes.

As loyal as she was, there were lines she wouldn’t cross.

It’s important to note here, that even an almost flawless story of achieving the American dream through hard work and integrity, isn’t without scrutiny.

Questions around potential conflicts of interest between her family’s business and her Cabinet duties have drawn media attention. Her political choices—especially serving under President Trump—have also sparked debate as noted by NPR in 2021.

But one thing’s clear: Elaine Chao’s story is deeply American. It’s about immigration, ambition, family, and the tension between public service and power."

PART 3: The Chao Sisters – A Family of Achievers 

"Before we go deeper into Elaine’s political career, let’s zoom out and look at the entire Chao family—because success didn’t stop with her.

Elaine is the eldest of six sisters, and every single one of them has carved out a noteworthy career.

For example, the late Angela Chao, the youngest, was the Chair and CEO of Foremost Group, the shipping company their father founded. She earned her MBA from Harvard as well and has served on numerous corporate and philanthropic boards, continuing the family’s legacy in global business.

Several of the other sisters have had distinguished careers in medicine, academia, and finance. One sister is a medical doctor; another is a legal scholar. Their accomplishments span industries—and reflect a shared ethic of hard work, excellence, and giving back.

The Chao parents didn’t just raise one standout daughter—they raised a dynasty of high achievers.

And to honor their mother Ruth’s lifelong passion for education, the family endowed the Ruth Mulan Chu Chao Center at Harvard Business School—the first building on the Harvard campus named after a woman of Asian descent.

It’s a powerful symbol of the family’s legacy and values.

 

She’s been praised as a pioneer for Asian Americans in government. She’s mentored countless young professionals, especially women of color. And she’s made a real mark on institutions—whether that’s turning around a nonprofit, expanding international programs, or modernizing U.S. infrastructure.

Remember that quote from Elaine at the beginning of this podcast?

On always remembering what it feels like to be an outsider? It’s a reminder that the way we see ourselves is often rooted in formative childhood years and experiences, and can be in stark contrast to the perceived excellence and effective leadership in adulthood.

We’ll close out with some of the things that have been said by those who have worked with Elaine Chao over her storied history:

From former U.S. Senator Chris Dodd, commenting on Elaine’s leadership in the Peace Corps, “She had this balanced, quiet confidence that knew what she believed in, and stood for, and her principles. But she also understood she had to work with other people and listen to others to get something done.”

From Carlos Guitierrez, 35th United States Secretary of Commerce, commenting on Elaine’s involvement during Hurricane Katrina, “I remember Secretary Chao just doing absolutely everything possible to help. In there, you could see her passion and her energy in the way she commits herself to a cause.”

From Condoleezza Rice, 66th U.S. Secretary of State: “The long hours and long days and there’s a significant amount of stress, but you stay focused on your dedication to making the United States a better place. And the best public servants are able to do that. Elaine Chao fits in that category, one of the best public servants I have known.”

"That wraps up today’s episode of Ladies and Legends. Whether you admire her policy stances or question her political alliances, Elaine Chao’s journey from a young immigrant in Queens to one of the most influential women in Washington deserves deep respect.

Thanks for listening. Be sure to follow the show, leave a review, and share this episode if you enjoyed it. I’m Juyun, and I’ll catch you next time on “Ladies and Legends."