The machinist and the internet 'hoax'

In 2006, Jack Goodman - a sailing enthusiast and retired machinist from Florida, came across a discussion of this brainteaser on a sailing forum he frequented. After considering the problem from an engineering standpoint, he decided to tackle to the task of building an actual model to convince his sailing friends that DDWFTTW was indeed possible.

He built and tested his device on a residential street near his house and taped the test while riding his bike and steering the model cart via radio control. Jack was more than satisfied with the results as were his friends who trusted his testing methods.

A friend of Jack's posted the video on YouTube for fun and all hell broke loose. Jack was accused of all manner of shenanigans -- some said he was having the cart towing with a fishing line during filming, others said he was running the cart on downhill street, hiding batteries and motors, placing the air indicator in a misleading location, powering it through stored gust energy, running the cart at a significant angle to the wind, weaving it back and forth to propel it like a skater, etc, etc.

Did Jack cheat? There will never be a way to know for sure, but this team intends to answer the question 'did he need to cheat' once and for all.