The Challenges and Rewards of Taildraggers, With Damian DelGaizo

By John Zimmerman
May 5, 2026
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Pilot's Discretion Podcast, episode 129

Tailwheel airplanes demand excellent situational awareness and sharp manual flying skills, two things that modern pilots often lack according to taildragger expert Damian DelGaizo. The longtime flight school owner, who learned from an aviation legend, talks about the finer points of three-point landings, wheel landings, and Piper Cubs. He also explains why a touch pass is important for evaluating grass runways and why you might have to carry a garbage bag full of rocks when flying skiplanes. In the Ready to Copy segment, Damian talks about dancing on the rudder pedals, how to fly with heel brakes, and teaching Harrison Ford to fly taildraggers.

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Quotes:

Why GA pilots struggle with landing: “I think a lack of situational awareness and a lack of stick and rudder skills, as simple as that.”
How tailwheel training has changed: “40 years ago, I could take a pilot that had been trained, let's say in the 60s or 70s, transition them into a tailwheel in probably five hours. And now it's probably close to double that.”
Three-point vs. wheel landings: “The three-point landing is much more difficult for a transitioning pilot to learn… You have to get the timing right”
Sizing up airplanes: “When you take a look at the airplane, take a look at the control harmony. What's the size of the elevator compared to the size of the rudder?”
Backcountry flying: “STOL and bush flying aren't exactly the same thing. Learning how to land absolutely short to win the Valdez competition is not like picking a spot to land in.”
Landing off airport: “You don't just look at a gravel bar and say, ‘yeah, I'm going to land there.’ Set up a practice approach. If it doesn't feel right, change one of the elements.”
Learning from an aviation legend: “he would have me bank the airplane and watch the rising wing with no rudder against a bank of clouds. And he could clearly see the wing rise and being pulled back by the drag of the aileron.”
Problems with modern flight training: “I think the basics are sort of rushed through because the instructor has a punch list of things that they need to get done on the way to the conveyor belt to solo.”
The benefits of training on grass runways: “If I'm training someone on grass and they're having trouble or if there's difficulty tracking the plane straight, I can let them go further before I have to jump in.”
Evaluating grass runways: “The best thing is a low pass, take a good look at it, and then maybe do a touch and go.”
Learning to fly on skis: “It'll take generally three or more seasons before you get to sample the different snow conditions. And your technique really does have to change”