it should be remembered that he had no competition. Anyone can win a one horse race - all you have to do is finish.
I think 'Pilot's main competition before 'Flyer' came along was the US mag 'Flying'. The latter has always been more aimed at turbocharged IFR, whereas 'Pilot' was more oriented to the grass roots aviator (though of course both did cater for both ends of the spectrum as well).
As for 'winning the race', I think 'Pilot's success was that it just a very good mag, competition or no. You can't slate it for not having competition if it's intrinsically done to a high standard (and Gilbert's 'Pilot' was).