I think the biggest missed opportunity would be the Scuderi Split-Cycle engine.
carbuzz.com: The Most Important Engine Of The 2000s May Have Been Lost To A Ponzi Scheme
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While the Scuderi Split-cycle engine may be very new (his patent was filed in July 2001), it is based on a design that's been around since 1914. Not to get too technical, but basically where a normal, Otto cycle engine (the internal combustion engine being used in most modern cars today) has four strokes to produce the engine's power, a split-cycle design divides the four strokes over two paired cylinders, one intake/compression cylinder and one power/exhaust cylinder. The two cylinders are then connected by a crossover port. This means that the workload is halved, in that only two strokes are needed to produce the power, instead of the four of the Otto cycle engine.
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It is unfortunate that the current inventor of the Scuderi engine, Carmelo Scuderi, died soon after filing his patent in 2001. His children started the process of bringing the engine into production in 2002 by founding the Scuderi Group, but troubles soon emerged with the authorities.
The family started raising money to further develop the ground-breaking engine technology, through investors, soon after Carmelo's death. But instead, according to court papers and reports at the time, it appeared as if the group was taking investor funding and using it for purposes like paying the family's salaries (of $2.9 million) from 2008 to 2011, and issuing bonuses for personal expenses.
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