Preparing aircraft before anyone had fought an air war was undoubtedly a struggle for pilots and engineers. The Royal B.E.2 was one of the first military aircraft put into serious industrial production, with a run of around 3500 aircraft. First flown in 1912, it remained in service until 1919, with its responsibilities steadily declining as better aircraft became available.

In a sense, the B.E.2 inspired the first generation of fighters by displaying all of the qualities that no one wanted in a fighter aircraft, including poor visibility, poor reliability, difficulty of control, slow speed, and weak armament. The advent of the Fokker Eindecker made the B.E.2 positively hazardous to fly. Refinements often hurt more than they helped, with the plane becoming steadily more dangerous and accident prone as grew heavier.

It’s tough to give a failing grade to a first effort. But the B.E.2’s difficulty and poor reliability, combined with the British decision to keep it in service well beyond its freshness date, earn it a spot on this list. Incidentally, the failure of the Royal Flying Corps to effectively substitute for the B.E.2 in a timely fashion provided much grist for early advocates of the Royal Air Force, the world’s first independent air force.

But the Flogger was a beast to fly and to maintain. American “Red Eagle” pilots, tasked with determining the capabilities of Soviet aircraft, considered the Flogger a disaster waiting to happen. In 1984, Lieutenant General Robert M. Bond died flying a USAF operated Flogger. A relatively large aircraft, the Flogger also lacked many of the best qualities of its predecessors, including a small visual profile.

The MiG-23 was initially intended to fill out the air forces of the Warsaw Pact, but the Soviet clients generally preferred to keep their Fishbeds. Indeed, in export terms the MiG-23 was essentially a cheap loss-leader for the Soviet engine and technical support industries, as it proved remarkably difficult to safely keep in service. By design, engines burned out quickly, meaning that export customers who had fallen out of Soviet graces quickly lost the use of their fighters. The Flogger’s combat record, generally in Syrian, Iraqi, and Libyan service, has not been positive. It’s hardly surprising that the MiG-23 will almost certainly leave service before its predecessor, the MiG-21