Lightly mash 1 cup of the raspberries in a bowl. Pour in the gin and let macerate at room temperature for 2 hours. Place the raspberries and gin in a blender and blend until smooth, about 20 seconds. Place a fine-mesh strainer over a medium bowl and strain the mixture. Discard the solids.
Rinse the blender and add the raspberry mixture, wine, lime juice, simple syrup, Kirsch, and ice cubes. Blend until the ice is crushed, about 10 seconds. Pour into 6 cocktail glasses and add a fresh raspberry to each glass.