Some date the beginning of business aviation to the first hardware store owner who painted his logo on a Jenny’s fuselage. Others cite the appearance of sophisticated cabin singles such as the Spartan Executive and Beech Staggerwing in the early 1930s, though most of those airplanes were owner-flown, not professionally driven. Still others jump straight to the advent of the original Grumman Gulfstream I turboprop and the ubiquitous Learjet in the 1960s.
Often overlooked is that glorious postwar period when corporate warriors rode into battle aboard civilianized bombers, sitting in kangaroo-skinned armchairs and bracketed by World War II radials with straight pipes. It was a prosperous time, with plenty of willing corporate pilots wearing the ruptured-duck lapel pins of WWII vets. Surplus warbirds were available for a dime on the dollar.
There were bizbirds ranging from the Grumman F6F Hellcat Little Nugget, flown by the CEO of Alaska Airlines on his executive rounds and painted to match his airliners, to converted B-17s and B-24s. Chicago Tribune owner Colonel Robert McCormick traveled in a B-17 equipped with a bar, a library and a well-padded swivel chair in the Plexiglas nose. One of the oddest converted warbirds was a Grumman FM-2 Wildcat that had a small four-place cabin behind and below the cockpit, with windows just above the trailing edge of the wing.
Many twin-engine North American B-25s and Douglas B-26s were civilianized. These bombers were noisy and extreme enough to get everyone’s attention on an airport ramp, and companies sprang up to do the modification and accessorizing work necessary to turn them into bizprops. The U.S. Navy’s Lockheed maritime patrol bombers, particularly the Lodestar and Ventura, constituted another family of combat twins that figured prominently in the business plane marketplace. Big-bellied and commodious, the Lockheeds would carve out a prominent niche in the postwar civilian market.
One very special Ventura derivative, the Howard 500, would come to occupy the very top of the boardroom-bomber food chain, even though it was a commercial failure.
Dee Howard was a classic American entrepreneur, inventor and self-taught engineer. Born in 1915, he never finished ninth grade and went to work at age 15 in an automotive shop. Within a year, he found a job as an aircraft mechanic’s helper and quickly climbed up the ladder of aviation jobs and FAA ratings to become a mechanic for Braniff Airlines.
Howard eventually formed his own company, Howard Aero, in 1947 and created the Howard 250 and 350—civilianized Lockheed Lodestars. His ultimate design, however, produced with the help of Ed Swearingen, was the Howard 500, an all-new pressurized fuselage with Ventura outer wings, Harpoon landing gear, Pratt & Whitney R-2800 engines and sumptuous 12-seat (typically) interiors.
After certification delays in the early 1960s, the airplane found itself competing with the new, substantially more capable Gulfstream I, the first purpose-built turboprop business aircraft. Dee Howard saw the Grumman coming, but he believed that a $565,000 pressurized piston twin able to burn widely available avgas and even use dirt strips would be at least as attractive as a twice-as-expensive turboprop. Howard simply could not imagine companies paying more than a million dollars for an airplane, but he was wrong. Only 17 500s were ever built, while the Gulfstream I went on to become the progenitor of a vast line of business jets, the most expensive of which go for $38 million.
The Howard 500 was the world’s last production radial-engine passenger transport and the most advanced piston twin ever built, civil or military. Today, only two are still flying, both owned by Howard maven Tony Phillippi, who also owns two non-flying 500s.
“Their ramp presence is unbelievable,” he says, and claims to have sealed deals simply by arriving in a 500. His N500LN was owned and flown during the 1970s by Forrest Bird, known in the aviation world as the creator of the Bird Innovator, a four-engine version of the PBY amphibian.
Bird sold N500LN, Lady of the Night, to a British industrialist. It spent many years flying around Britain and Europe, then sat largely dormant in a UK hangar for a couple of decades until Phillippi bought it in 2009 and did the work required to get it airworthy again. After a precautionary landing in Salzburg, Austria, Phillippi had the R-2800 engines shipped for overhaul to Anderson Aeromotive, in Idaho, then back to Salzburg for installation by the renowned Red Bull aviation collection’s shop.
Once it was flyable again, Phillippi ferried the 500 back to his own facility, TP Aero, in Eagan, Minn., and began a four-year restoration. “The interior was original, from the ’60s, and to be polite, you could call it tattered,” Phillippi admits. “We restored it to its original Texas cowboy condition, with two bars and 12 seats.” TP Aero also added as much soundproofing as possible, and Phillippi claims that despite its panoramic cabin windows, N500LN “is church-quiet now.”
The single biggest systems job was finding a replacement cabin supercharger—the engine-driven compressor that provides the 500’s impressive 6.75-psi pressurization—and fabricating the driveshaft that spun it. The shaft is a highly stressed, heat-treated, Howard-specific part, but Phillippi finally found a fabricator who could do the job.
Despite the four years of rebuilding, keeping N500LN flying is the gift that keeps on giving. “I don’t want to know how many hours of maintenance are needed per flight hour, but it’s probably about 20,” Phillippi says. “Which is the full-time work of a very good $125,000-a-year mechanic, so it’s not that big a number when you’re considering an airplane this complex.” To operate the 500 at its fullest potential would require hard-to-find 145-octane gasoline, so Phillippi burns 100LL. “I don’t need to be running around at 325 knots,” he says. “I’m real happy at 260.”
For years the rumor has persisted that Elvis Presley owned a Howard 500. “That’s a myth,” Phillippi points out. “The Seeburg jukebox company owned Hotel Papa [Phillippi’s second flying 500, N500HP], and they used to provide it to Presley for his use.”
N500LN is currently for sale, and estimates of its worth have run from $2.5 to $8.5 million. Is it an obsolete old boardroom bomber or is it in some ways the ultimate bizplane? Phillippi favors the latter. “If you want to make a Gulfstream G650 simply disappear,” he says, “just pull up on the ramp next to it with this airplane.”
This article originally appeared in the March 2019 issue of Aviation History. Subscribe here!