Master of the Air: Recalling a Close Encounter With Rob Holland

Backcountry flight with late aerobatic star remains a cherished memory.

Aerobatic pilot Rob Holland was killed in an accident when his plane crashed on approach into Langley Air Force Base on April 24, 2025. [Courtesy: Kyle Newsom]
Gemini Sparkle

Key Takeaways:

  • The author recounts a memorable flight with renowned aerobatic pilot Rob Holland, emphasizing the unique and cherished nature of the experience.
  • The flight involved landing and taking off from challenging, unusual grass airstrips in a Carbon Cub, showcasing Holland's skill and mentorship.
  • Holland's kindness, humility, and passion for flying are highlighted, contrasting his professional accomplishments with his down-to-earth personality.
  • The author concludes by encouraging readers to attend airshows and share their passion for aviation, honoring Holland's legacy.
See a mistake? Contact us.

Like many of us, I have a few special flying memories in my logbook that stand out because they only have one entry.

For example, taking my grandfather for our one and only flight after years of training and earning my pilot certificate. Riding as a passenger on the Collings Foundation’s B-17 Flying Fortress Nine-O-Nine is another.

This Article First Appeared in FLYING Magazine

If you're not already a subscriber, what are you waiting for? Subscribe today to get the issue as soon as it is released in either Print or Digital formats.

Subscribe Now

I was recently reminded just how special some of those moments can be when, during the last week of April, the aviation community lost one of its most talented and respected aerobatic pilots, Rob Holland. Back when I was just beginning my career in the industry, a chance meeting between Holland at an airshow sparked a conversation and led to a memorable flight and logbook entry that I’ll always cherish. 

I had met very few pilots of Holland’s stature at the time. I had no idea that both he and I were flying out of the same airfield in Nashua, New Hampshire (KASH). Holland had always called Nashua home, having graduated from Daniel Webster College’s aviation program, which closed in 2017, but was located right at the airfield, about a half-mile away from his hangar. 

It was October 2016, and I was working on my complex endorsement, renting a Piper Arrow III from East Coast Aero Club, one of the few flight schools located on the field. Our conversations grew into an offer Holland made for me to join him for a flight on one beautiful, warm CAVU fall day in New England—the kind of weather in October that feels like the last blush of summer. 

Although we only flew together once, it remains one of my favorite flights in my logbook. 

We borrowed his friend’s Carbon Cub. I was happily expecting to occupy the rear seat to watch Holland share the finer points of backcountry tailwheel flying. Instead, he insisted I take the front seat, even after I questioned his judgment, allowing a green 150-hour private pilot to sit in front of a 15,000-hour professional aerobatic pilot. However, he assured me we’d have a lot of fun. And we did. 

He took me to four grass airstrips in the southeast corner of New Hampshire—most of them private (air)fields, where he knew the owners. From above, these looked like small roads cut into the pine forest, not exactly what qualified as a “field” by my definition. He assured me the Cub’s wings would clear the trees on either side of the airstrip (which they did—with plenty of margin), and he followed me on the controls, politely, quietly, and calmly encouraging me to try the landings. I was confident that he was confident that he would never let me get in over my head. And so my introduction to backcountry flying was—and will forever be—with Holland guiding me through these nonstandard approaches to hidden-gem grass airstrips. 

Though I completed my flight training in New Hampshire, I never knew so many small fields existed. My favorite landing from our flight together was quite literally a farmer’s field, but this one was different from your standard boulder-pocked variety. One side of the field was well-mowed and cared for but ended in an abrupt uphill ascent. Approaching the field from the air, we established a downwind leg, and he matter-of-factly described our plan for landing—to which I replied, “We’re going to land on that?” The answer was “yes,” and putting aside my incredulity, I focused on the landing, and with some quiet assistance from the backseat, we were safely on the ground in less than a minute. 

The author has nothing but fond memories of his one-time flight with aerobatic pilot star Rob Holland (rear). [Courtesy: Sean Siff]

When the Carbon Cub dropped to an acceptable speed, I pulled full aft on the stick. We rolled up to the hill at the end of the field, and I smoothly advanced the throttle on Holland’s instructions so that we carried enough forward momentum to get the airplane to the top. There was ample room on the hilltop to swing the tail around to prepare for takeoff. 

When it came to the takeoff roll, Holland wasn’t kidding when he described that we would be off the ground in a matter of feet. With toes on the brakes, I held us at full power, released the brakes, and we rolled downhill and were off the ground in a few seconds. Holland directed me to keep us safely in ground effect to build airspeed then pull back on the stick—and up into the air we went. Being used to the spacious and flat runways of my private pilot training, this takeoff remains my favorite. 

Afterward, I joined Holland for some midday breakfast at one of his favorite breakfast joints, the Airfield Cafe at Hampton Airfield (7B3). While I was completely worn out from trying to learn as much as I could, for Holland the morning’s accomplishments would hardly qualify as a warmup. I joked with him that it was a good thing that we could open the right-side window on the Carbon Cub as I had burned off my underarm deodorant much earlier in our flight. I remember he laughed, displaying his usual kindness and humility.  

Over our breakfast, I learned in addition to being Granite Staters, we both liked some of the same rock ’n’ roll bands and enjoyed playing music. He could play a lot of Van Halen songs on guitar, and I told him that I would back him up on the drums once I could play some of Alex Van Halen’s incredible fills. Back at his hangar that afternoon, he ripped through a few Van Halen guitar solos with the same gusto of his aerobatic performances.

Sharing the Cub flight with me was just one small example of the thousands of kind acts Holland bestowed on friends, family, and fans alike, and it was these acts that marked his life. Reading remembrances from those who were fortunate to know him better than I did, it was clear that he generously shared his gifts with many of us. 

Although my professional life soon took me away from Nashua Airport, Holland and I stayed in touch, exchanging occasional photos from where we found ourselves in life.

Jacques Cousteau once said that “when one man, for whatever reason, has the opportunity to lead an extraordinary life, he has no right to keep it to himself.” Rob Holland embodied that. 

I happened to be at an airshow for work in late April when I learned that Holland had crashed while landing at Langley Air Force Base (KLFI), where he was scheduled to perform. It was a very challenging weekend to be at an airshow, knowing that one of our country’s most innovative and accomplished aerobatic pilots had been taken from us too early and would no longer be able to share his passion for flying. 

However, being there also reminded me why aerobatic pilots are such an important part of the aviation experience in our country. It was cathartic to share in the spectacle of watching the aerial performers display their craft in front of thousands of other aviation enthusiasts.

In the days following his death, my social media channels were appropriately aglow with touching tributes highlighting Holland’s dedication to the aerobatic flight profession. Fortunately, there is a lot of video footage of his flying performances, descriptions of his maneuvers, and interviews. These will serve as a fitting reminder of a life well-lived, dedicated to the craft, and will serve to inspire future aerobatic pilots who can study and learn from Holland’s performances. He coined the now-popular mantra of “Fly Good, Don’t Suck” but will be remembered for much more. 

As a civilian pilot, he earned the respect and friendship of the U.S. Navy’s Blue Angels and was made an honorary Blue Angel—a sign of mutual respect shown to a select few. He also spent time at the other end of the pilot spectrum, gladly signing fan autographs and patiently explaining how he got to live his dream doing what he loved, one day at a time, just trying to make each performance better than the last. 

Perhaps you’ll consider attending an airshow this summer. There you’ll see every generation in attendance, from grandparents down to the youngest attendees, in whose minds lie the opportunity for the first seeds of aviation to be planted for the very first time. You will get to see a series of aerobatic performances flown by civilian and military pilots who bravely commit 100-percent effort to inspire and remind us of why we look to the sky in awe, excitement, and wonder in the first place.

Even better, take a friend, neighbor, or family member who has never been to an airshow before. In doing so, you can be the one who lights the fire for a passion for aviation in another person. I know Rob would appreciate that.


This feature first appeared in the July Issue 960 of the FLYING print edition.

Sean Siff

Sean Siff is a private pilot who has worked in marketing in the aviation industry. He’s an active flight sim user as he works to stay current in the airplane.
Pilot in aircraft
Sign-up for newsletters & special offers!

Get the latest stories & special offers delivered directly to your inbox.

SUBSCRIBE