By Joanna Plichta Boisen
Most lawyers find their way into an industry. Kyle Levine was born into one.
He was raised in an airline family in Denver, where aviation wasn’t just a curiosity — it came with the house. His father was a pilot and his mother a former flight attendant, and layover stories and airline talk were standard conversation at the dinner table. By the time Kyle completed Stanford University, he was a licensed pilot, and seriously considered following his father into a life in the skies. But careers, like flight plans, rarely follow a straight path.
Instead of a flight deck, Kyle chose a law school classroom.
Trading flight hours for casebooks, Kyle earned his Juris Doctor from Southern Methodist University, hoping to pursue aviation law. The path made sense. Aviation was deeply familiar terrain, and he discovered it spoke to his natural analytical, argumentative, and dramatic sides, practicing first at Mendes & Mount in L.A. and then at Nixon Peabody in San Francisco.
What he did not expect, however, was that his personal life would forever alter his plans for private practice. Flying north nearly every weekend to visit his long-distance partner, Craig Pepin, a Seattle-based gastroenterologist, introduced Kyle to Alaska Airlines. In time, it also clarified what he wanted next: a chance to build, not just advise, inside an industry he had loved his whole life.
In 2006, the airline Kyle first came to know from seat 12A became the place where he built a career, joining Alaska’s legal division as senior commercial and regulatory counsel. About a dozen promotions later (an impressive streak by any measure, especially scroll endurance), Kyle now serves as Alaska Airlines’ Chief Legal Officer (CLO). Since stepping into the role in 2016, his responsibilities have continued to expand. Today, he also oversees the company’s government and public affairs team, adding public policy and external engagement to an already broad remit.
In reflecting on being a CLO, he is refreshingly candid, and unmistakably happy. It is, he says, a dream job for someone who loves the intellectual challenge of practicing law in a highly regulated business, enjoys influencing outcomes, and does not shy away from conflict, constant change, or the certainty of never being bored. Aviation rarely allows for quiet stretches, and Kyle wouldn’t want it any other way.
What has kept him at Alaska for so long is not just the role itself, but the respect the legal department is shown within the company. The legal team is involved early, not pulled in after the fact, a shift Kyle credits to leadership that values transparency and shared responsibility. Information moves quickly. Collaboration is real. Safety and compliance outrank everything else. Employees across the airline are empowered to pause operations when something does not feel right, and that same responsibility carries through to the lawyers and compliance professionals advising behind the scenes to protect safety, ethics, and public trust.
But for Kyle, culture matters as much as the decisions it shapes. When he talks about what has kept him at Alaska for nearly two decades, he rarely starts with titles or transactions. He starts with people. Colleagues across the organization. His team. The pilots, flight attendants, customer service agents, and countless others who carry the operation forward each day, knowing he played a part in their ability to do their jobs safely and well. Even after years of growth, Alaska still feels more like a community than a corporation to him.
That emphasis on people also shapes the way Kyle leads. At his best, he considers himself casual, approachable, collaborative, and non-hierarchical. At his worst, he considers himself impatient, bossy, and occasionally cynical. His team, I suspect, might point out that many of the qualities he critiques most harshly in himself often look, in practice, a lot like high standards, sharp instincts, a quick wit, and deep loyalty to the people he leads.
That instinct to create room for people did not emerge in isolation. Mentorship has shaped him deeply. Among those who left a lasting impression is Phyllis Campbell, who at the time served as Alaska Airlines’ lead independent director. At Kyle’s first board meeting, sensing his nerves as he joined the directors’ table, she leaned toward him and whispered, “Sit next to me. You belong here.” He has never forgotten the generosity of that moment and has tried to create the same sense of belonging for others ever since. It reflected the kind of leader he always strived to be, and the one he is known for being today: generous with encouragement and quick to make space for others.
And of course, the job has tested him. The most difficult moments of Kyle’s career trace many of the defining challenges facing modern aviation: the regulatory review surrounding Alaska’s acquisition of Virgin America in 2016, the Hawaiian Airlines acquisition nearly a decade later, serving as CLO through the uncertainty and operational upheaval of COVID, and responding to in-flight emergencies where nothing about the moment feels theoretical or distant. None of it was easy. All of it reinforced the sense of shared duty that emerges when stakes are high and the margin for error is nonexistent.
And yet, even in high-stakes moments, Kyle keeps things impressively human. When he needs to raise a sensitive or high-risk issue with senior leadership and senses their patience for a traditional legal presentation is thinning, he adapts. Quite literally. Once, facing a particularly high-stakes class action, he rewrote Prince’s “Let’s Go Crazy” to walk the executive team through the risk. It was unexpected. It was memorable. Most importantly, it kept everyone listening long enough for the message to land. It turns out even executives appreciate a legal warning delivered with a beat.
That same charisma and warmth follows Kyle home. According to those who know and love him best, Kyle is energetic, social, decisive, and simply a great human. Craig, his partner, offers one additional adjective with zero hesitation: messy. Depending on your perspective, this is either a character flaw or Kyle’s devotion to proving that every flat surface is, at heart, a storage solution.
When things pile up on land, Kyle knows exactly where to go. He swims with the Masters competitive swimming community, spending as much time as possible in the water, on it, or nearby. This is where he resets. In the pool, the stresses of the day disappear.
And while the calm rarely lasts, the clarity does. Whether navigating regulation, leading through crisis, or explaining legal risk through Prince lyrics, Kyle is still doing what he has always done best: bringing clarity and steady judgment to complex operations and the teams responsible for keeping them moving when the stakes are high. He may not have followed his father into the cockpit, but he never really left the world that first captivated him as a child. He simply found a different seat from which to help keep it moving forward.
The travel benefits aren’t too shabby, either.
Joanna Plichta Boisen is Chief Pro Bono & Social Impact Officer at Davis Wright Tremaine. Her day job is do-goodery. Her side hustle is telling stories about extraordinary people worth knowing.
