Flying the Flight Levels with Rob and Bill

Life’s better when flying with real-deal pilots.

“Outta sixteen-four for two three oh. Lotta guys miss that call.” I sit there wondering if this is for real. It isn’t. It is just Bill being Bill. On another trip, after grinding westward for four hours into 60-knot headwinds, I turned southwest as instructed by approach control to set up for the RNAV 4L at Midway International Airport in Chicago (KMDW). The airplane and its occupants are exhausted. Quietly, I hear Rob say, “We can save about 15 miles if we go direct to the airport. Want me to call the field?”

Of course, that’s the right thing to do. I wish I’d thought of that myself. It wasn’t a command and it wasn’t a rebuke. It’s just Rob being Rob.

Other than a sense of humor, what do these two guys have in common? Fifty-thousand hours of flight time, for one. Multiple type ratings, for another. General aviation backgrounds turned into “to-die-for” airline careers. Resilience, generosity, and faith most of all. Finally, how come I got lucky enough to know both?


I met Rob first, almost 20 years ago. At the time, he was regional chief pilot for Southwest Airlines in Dallas. When I spotted a copy of Ernest K. Gann’s Fate Is the Hunter on his bookshelf, we were off to the races, vying to finish each of Gann’s poetic sentences for the other. Soon Rob became my airline guru. I was stunned that a man in such a high position would bother with a surgeon pilot wannabe, but he did, nonetheless.

We became good friends, though the relationship was all one way. Most of our aviating could be called “hangar flying.” I would call Rob with a proposed flight and ask his guidance. His voice was always steady, and he taught me that almost all flights could be concluded safely if you were careful. When we flew together in my Piper Cheyenne, I always mimicked my impression of an air-line pilot. He indulged this, responding to my idea of a callout with a grave response that did not betray a hint of amusement, much less condescension. When I got a Raytheon Premier I jet, Rob acted as if he’d never seen a jet do 0.78 Mach before. I love this man.

Bill came into my logbook just a few years ago. Retired from American Airlines, he was an instructor and I was a client at Simcom on the Cessna Citation CJ1. After our first sim session, he took me aside and told me I didn’t fly like most owner-operators. I explained that I had flown Part 135 full time—an experience that changed me from a “doctor in a Bonanza” to a real pilot. He told me he was going to take over a CJ2+ for a business in Hilton Head, South Carolina, and asked if I thought a mutual friend of ours might be interested in being a contract copilot. Without a hint of shame or modesty, I replied, “Hey, what about me?” This turned out to be providential.

Rob flew Cessna 310s, Citations, Lear 24s, Cheyennes, and a ton of other stuff. He owned a flight school and was hired by American just in time to be furloughed. He jumped at a chance to fly for a small regional airline in his home state. He made captain by age 29 and retired as No. 1 of 11,000 pilots at Southwest.

Bill flew Cessnas, Mooneys, and Pipers. He was the sky watch traffic reporter in Orlando, Florida, and has an announcer’s voice to match. As a freight dog he flew Cessna 400 series and Lear 23s. For corporate America he flew Jetstars, Falcons, Citations, King Airs, and Sabreliners.

From the cups of these aviators, I have sipped many a story, a lot of wisdom, and a few good tricks. Humor, resilience, friendship, generosity, and faith have marked all of our interactions.

Whereas most of my flying with Rob has been in his airplane or mine, my flying with Bill has largely been “professional,” which is to say in the CJ2+. When flying to Hilton Head one day with the boss in the back, we were confronted with, well, a confrontational front. A line of severe thunderstorms straddled the destination and showed no signs of moving. The controller said the storms were “freight-training” along the front. It certainly looked to be the case. One cell after the other tracked along the line. You could almost hear the track crossing warning bell ring.

I voted for deviation to Savannah, Georgia, and a rental car for the boss. Bill, with all that experience, asked approach control for a hold. “Call the tower,” he said. “Ask for up-to-date conditions.” The tower said heavy rain, visibility quarter mile, and tornado sirens going off in all quadrants.

But I kept listening. Two circuits of hold later, I heard taxi instructions to an airplane on the tower frequency. If somebody was taxiing for takeoff, the weather must have improved. When queried, the tower reported 500-foot overcast visibility 5 miles, wind 050 at 6, and light rain. We landed soon thereafter.

That wasn’t the first time I saw Bill make the weather change for our benefit. I sat with a forlorn attitude looking at the impossible weather on our approach to Key West, Florida. Coming from Cancun, Mexico, we had no customs alternatives except to land at Key West. All I could see on the radar was red. I was dumbfounded to hear Bill exclaim in his optimistic way, “See, he’s taking us down the back side of all this, then he’ll turn us inbound. Perfect.” Suddenly, it was. The clouds had parted. We call this the “Red Sea” effect.

Rob has been generous with sharing his love of Texas with me. We conquered Marfa in my CJ1, laid on the runway at his fly-in home outside of Kerrville at night watching the stars while the asphalt gave back the day’s heat onto our backs, and dug deep into Cooper’s Old Time Pit Bar-B-Que in Llano in his Columbia.

“You want this leg?”

It’s Bill again. Forget the fact that the weather is terrible and all three top officers of the company are in the back. We have just had two great dinners together in New Orleans. Our conversations include flying, families, and the spiritual. Bill is deeply religious and knows I am less so. He never imposes his views on me, but I find myself feeling the power of his faith.

Same goes with Rob. When I apologized for sending him a bible quote with a note hoping he wouldn’t find it disingenuous, his response filled my heart.

“You’re a better Christian than many ‘Christians’ I know,” he said.

May each of us have such generous pilot mentor friends.

This column first appeared in the July 2023/Issue 933 print edition of FLYING.


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