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Is it possible Jessup wasn't quite as competitive back then as it is now, and NLS was into mooting before it was cool (which obviously makes NLS the OG mooting hipsters)?
No, because NLSIU won it twice, both during the 90s and 2010s. It needs to be asked by other NLUs have not won. There may be deeper reasons, such as wrong team selection, lack of support from admin etc.
Because other than a handful of people, nobody cares that much about mooting anymore. It creates paper tigers, not actual lawyers.
Why has Arsenal never won a Champions League? This would be more relevant compared to your present daft question.
Dipen was a once in a generation star. Sapna and Priya were fantastic mooters too, not taking anything away from them, but Dipen....