One afternoon in January 2001, Chris Pappaioanou, a customer service agent with Great Lakes Airlines, was loading luggage at Telluride’s airport for a flight heading to Phoenix when he handed his résumé to Mesa Airlines CEO Jonathan Ornstein, who was boarding a plane.
Weeks later, Pappaioanou was hired to be the Mesa’s vice president of legal affairs.
More than two decades later, he is one of the most influential and respected executives at Irving-based Envoy Air, a regional airline and a wholly-owned subsidiary of American Airlines, where he serves as vice president of legal, labor and employment and oversees all litigation and regulatory compliance matters.
During the past two years, Pappaioanou negotiated a transformative, industry leading collective bargaining agreement that reversed attrition within Envoy Air’s pilot ranks and attracted hundreds of new pilots to the airline. He also led several legal victories, including the resolution of a biometrics privacy suit in Illinois and a successful resolution to a wage and hour class action suit in California. And he was instrumental in the restructuring of Envoy Air’s human resources and legal departments to better align with the airline’s current needs as it continues to experience growth.
“The real reason he is a great lawyer and great leader is because he is a great person,” said Greenberg Traurig shareholder Stephanie Quincy. “He has not lost his humanity despite working in a very competitive corporate environment and challenging industry. So many attorneys seem to forget that doing the right thing is important and instead become focused solely on ‘winning.’ Chris keeps the big picture in mind including fairness overall. He looks to partner with people rather than seeing them as adversaries.”
“I have known Chris for well over 20 years,” Quincy said. “The core person Chris is will never change. He absolutely loves the airline industry and loves people. He is a good person who treats all people with great respect.”
But it all points back to that cold Colorado day when the Mesa CEO saw something special in the guy loading his luggage.
The Association of Corporate Counsel’s DFW Chapter and The Texas Lawbook announce that Pappaioanou is one of two finalists for the 2023 DFW Corporate Counsel Award for Senior Counsel of the Year for a Small Legal Department, which is less than five attorneys.
Premium Subscriber Q&A: The Lawbook spoke with the DFW Corporate Counsel Award for Senior Counsel of the Year for a Small Legal Department finalist about his best day at Envoy Air, major career successes, and the only way outside counsel can reach him.
ACC-DFW and The Lawbook will honor the finalists and announce the winners on Jan. 25 at the annual DFW Corporate Counsel Awards ceremony at the George W. Bush Institute.
“One of Chris’ greatest strengths is his incredible knowledge of the airline industry generally and Envoy’s business and operations specifically,” said O’Melveny & Myers partner Mark Robertson. “Because of this intimate knowledge, Chris is able to make key strategy decisions incredibly quickly and accurately. Another strength is his ability to always move forward in a positive direction even when things are not going well and keep a positive attitude.”
Robertson said Pappaioanou possesses a “high emotional intelligence, which allows him to read people and situations to make determinations as to what arguments and positions will work.”
Envoy Air officials, in making the award nomination, said Pappaioanou “thrives” in the highly regulated, heavily unionized pressure cooker that is the commercial airline industry.
“Chris has a unique ability of approaching problems from new angles, of leading both colleagues and negotiating partners to new perspectives for addressing complicated challenges and potential impasses,” Envoy wrote in its nomination. “Chris is always the one in negotiations who leads with ‘Why can’t we do this?’ rather than sticking to ‘This is how we have always done it.’ If you encountered Chris in the office, you would never expect the full weight of the responsibility that falls squarely on his shoulders.”
“Chris is well-known for his generous support in the office, maintaining a true open-door policy and a commitment to mentoring his team members. Chris’ commitment to teamwork is inspiring as is his ability to lead with empathy, always finding an effective method to deliver tough advice,” Envoy Air officials wrote.
Katie Lyons Wall, a partner at Jones Day in Dallas, said the challenges Envoy faced following the pandemic could never have been anticipated.
“Chris maintains a calm, reasonable perspective and provides strategic counsel that the business trusts, respects and relies on,” Wall said. “Although he’s in Legal, Chris thinks about the big picture, creating business solutions that organization seeks him out for.”
Pappaioanou was born in Charlotte, North Carolina, but he spent most of his first six years as a child in Tokyo for his parents’ work. The family then moved to Indiana where his mother was a pediatric surgical nurse at Riley’s Children’s Hospital in Indianapolis and his father worked as an executive at Union Carbide and Praxair.
With no lawyers in his family, law school was not even a thought growing up until a high school career counselor gave him the idea.
Pappaioanou went to college at Ball State University, the alma mater of David Letterman, where he received a degree in corporate financial management. He earned his law degree from Indiana University and an MBA from Yale University.
With the recommendation of a South Carolina lawyer named Neil Haldrup, Ogletree Deakins hired Pappaioanou in 1997 as a first-year associate working on labor and employment matters, which he said gave him “a solid foundation in employment litigation.”
In October 1999, he packed his bags and moved to Telluride, Colorado, where he worked for a solo practitioner taking any cases that walked in the door.
“While I would love to say I wanted to be an attorney there, I think the truth is closer to me wanting to be a ski bum for a couple years,” he said.
To make a little extra money, Pappaioanou worked as a station agent for Great Lakes Aviation, which was part of the United Express network of regional carriers.
“My uncle, David Linzinmeir, was a captain at US Airways for as long as I knew him, and growing up in an aviation family tends to draw you into the industry,” he said. “My background in labor and employment fit well into aviation, as airlines are regularly confronting complex issues involving both.”
Pappaioanou was working for Great Lakes Aviation in January 2001 when he heard that Mesa Airlines was conducting a conference in Telluride. Mesa had contracted with Great Lakes to handle its ground operations in Telluride.
“At some point I learned that Mesa’s general counsel had left the company shortly before and I asked someone who I should talk to about a position in the legal department,” he said.
A Mesa official told Pappaioanou that the company’s CEO, Jonathan Ornstein, would soon be arriving.
“So, I showed up with a résumé in hand,” he said. “Jonathan looked past my Great Lakes Airlines uniform and offered me my first in-house position a short time later. I can’t imagine my life and career without the benefit of [Ornstein and Haldrup] seeing my potential. The best part of the story is that Jonathan got his start in the airline business working the ramp for a small company in LA. We ended up speaking before their flight and shortly thereafter I traveled to Phoenix to meet again. I was offered a position and started in March 2001.”
For nine years, Pappaioanou was Mesa’s vice president of legal. In 2010, the Phoenix-headquartered airline promoted him to general counsel — a position he held for nearly four years.
In 2013, Honolulu-based go! Airlines, a low-cost airline that operated seven 50-seat CRJ-200 aircraft flying between the neighbor islands in Hawaii, hired Pappaioanou as its president.
Envoy Air executives hired Pappaioanou in March 2015 to handle its labor and employment matters. The regional airline promoted him to be vice president of legal in January 2022.
“I joined shortly after the company had emerged from bankruptcy and at the tail end of the merger between American Airlines and US Airways,” he said. “When I joined, Envoy had a cloudy future. Its fleet had contracted from over 300 aircraft to a projected fleet below 100, and a pilot shortage was beginning to impact the regional airline industry. Assisting in turning that trajectory around has been a tremendous challenge, but the most rewarding of my career.”
In its nomination, Envoy Air said Pappaioanou has experienced tremendous achievements in dealing with the four unions in the airline’s eight different labor groups.
“One of the reasons why Chris has been so successful in his role at Envoy is a profound sense of empathy that was cultivated through a true bootstrap rise through the airline industry,” Envoy officials wrote. “Chris’ first job was as a baggage handler. He has worked in a variety of positions on his rise through the airline industry, which not only affords him a unique perspective into employee concerns and conditions, but it affords him respect when he enters a room to engage with union representatives. Chris will always do well by his people and team. He sees the best in everyone, first and foremost, and will find ways to help his colleagues grow in their skills and career.”
Lawyers who have worked with Pappaioanou say that his people skills are the result of his belief in treating people fairly.
“The fact that in all of his years in employment law, the companies he has worked for have never gotten hit with large adverse verdict is an enormous achievement,” said Quincy. “He is excellent at assessing situations early and finding fixes where there have been problems and holding the line where needed. This is a very fine balance and it is easy to make a mistake. Another big feather in his cap is his strong relationship with the many unions he deals with. Again, he looks for ways to find solutions rather than pick fights. He finds commons ground and gets everyone there.”
Another example was the pilot shortages following the pandemic. Pappaioanou worked with the union, Envoy’s training department, and Envoy’s recruitment team to develop new strategies, programs and benefits to attract and retain pilots.
“Chris negotiated an agreement with Envoy’s pilot union that provided greater pay for Envoy pilots and also worked for the company,” said Robertson. “This agreement put Envoy in a competitive position to attract new pilots and meet heightened demand. In that regard, Chris has developed strong relationships with Envoy’s unions that allow him to work collaboratively to solve problems.”
Douglas Hall, a partner at Jones Day, said Pappaioanou is a good lawyer and leader because of his “willingness to ask questions, to listen to the answers he receives and to take that information into account appropriately in his decision-making.”
Hall said he was impressed when he and Pappaioanou worked together on critical union grievances. One involved a pilot who filed a complaint “regarding when the airline could inform pilots of their reserve assignments.”
“Chris’s leadership and vision in that case were crucial in leading our ultimately successful defense to the grievance,” Hall said. “Chris also showed exceptional judgment in a difficult case involving a pilot who was part of the ‘sovereign citizen’ movement and who made threatening comments towards employees of the airlines. Chris is a careful decision-maker. He knows what fights are worth fighting and when compromise is the better path. He quickly grasps the issues in cases and where each side’s strengths and weaknesses are.”
Lawyers who Pappaioanou has hired to handle matters say he is a pleasure to work for.
“Chris has so much to handle in his position, but he is on top of everything,” said Tracey Wallace, a partner at Spencer Fane. “He is strategic, direct and knowledgeable about all his cases. He considers all the potential alternatives and gives clear and concise instructions. He also makes sure that you know what he wants to accomplish. Chris has a great sense of humor and is very loyal.”