David Henderson, the businessman who organised the flight that crashed, leading to the death of footballer Emiliano Sala, was sentenced to 18 months in prison at Cardiff Crown Court on Friday.
Henderson, 67, was accused of a failure to follow safety protocols that caused the death of 28-year-old Argentine Sala and pilot David Ibbotson when their plane crashed into the English Channel on a flight from Nantes to Cardiff in January 2019.
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The judge, Mr Justice Foxton, said: "You sent numerous messages to Mr Ibbotson; I'm sure these messages illustrate a lurking doubt as to whether he was fully up to the job."
Last month, Henderson was found guilty by the court of endangering the safety of the aircraft.
Henderson had previously pleaded guilty to trying to arrange a flight without permission or authorisation but had denied the charge of endangering the safety of an aircraft.
At the trial, prosecutor Martin Goudie QC said Henderson had cut costs "at the expense of safety."
The body of Sala, who had signed for Cardiff City in a £15 million ($20.10m) transfer only days earlier, was found a month later. Ibbotson's body has still not been recovered.
The trial heard that Ibbotson, who regularly flew for Henderson, did not hold a commercial pilot's licence or a qualification to fly at night.