We're not sure if Arthur Welsh was the first Jew to pilot an airplane, but...
The young Laibel Welcher immigrated to America from Russia in 1890 and then changed his name to something less Jewy. Enamored with airplanes, the newly-monickered Arthur "Al" Welsh applied for a job with the Wright Brothers. Initially rejected because of lack of qualifications, he pressed on. Eventually, Orville Wright personally taught Welsh to fly. By 1910, he became an instructor in the Wright Flying School.
Welsh wasn't simply a teacher; he set multiple records for speed and altitude. Alas, like many early aviators, it didn't last. In 1912, his airplane crashed when making a turn, and that was that for Al Welsh.
So was he the first Jew to pilot a plane? Probably, but it's impossible to say. Let's just call Al Welsh a pioneer Jewish aviator, and leave it at that.