In medium skillet over medium-high heat, cook drained pineapple, 1/4 cup sugar, and a pinch of salt, stirring occasionally until the pineapple is lightly browned and the liquid evaporates, about 15 minutes.
In a food processor, process pineapple mixture until smooth, about one minute. Set aside. In medium bowl, whisk together the egg yolks, 1/4 cup sugar, and 1/4 teaspoon salt. Set aside.
In medium sauce pan, combine gelatin and 1/2 cup of pineapple juice concentrate. Allow to sit until the gelatin softens, about 5 minutes. Cook over medium heat until the gelatin dissolves and the mixture is very hot but not boiling, about 2 minutes.
Whisking vigorously, slowly add the gelatin mixture to the egg yolks. Return the yolk mixture to the saucepan and cook, stirring constantly, until slightly thickened, about 2 minutes.
Remove from heat and stir in the remaining 1/2 cup pineapple juice concentrate and processed pineapple mixture. Pour mixture into a bowl and refrigerate until set, about 1 1/2 hours.
Meanwhile, in a standing mixer, whip heavy cream with remaining 1 tablespoon of sugar on medium-high speed to stiff peaks, about 3 minutes.
Working with 1 cup of whipped cream at a time, fold 2 cups whipped cream total into chilled pineapple mixture. Scrape mixture into cooled crust and smooth the top.
Top with remaining whipped cream. Refrigerate until set, at least 4 hours or overnight. Store leftovers in the refrigerator.