For Cooked Starter: Combine ingredients in small saucepan. Cook on medium heat about 5 min., whisking constantly until whisk leaves a trail on bottom of pan. Cool to room temperature.
For Dough: Heat milk to 90°F. Sprinkle yeast over milk. Let stand while assembling remaining ingredients.
Combine flour, sugar and salt in bowl of mixer fitted with dough hook. Add eggs, milk mixture and Cooked Starter. Mix on low speed 4 min. or until smooth. Add butter. Mix on medium speed about 10 min. (Dough will be tacky.) Mix in cookie pieces just until blended.
Place dough in large greased bowl, turning to coat entire surface. Cover with plastic wrap. Let rise at room temperature 1 hour. Turn dough onto lightly floured surface. Deflate and shape into a rectangle to fit 13x4x4-inch Pullman loaf pan. Let dough rest 15 min. Place in greased pan. Cover with lid. Proof 45 min. or until dough is three-fourths the height of pan.
Bake in 350°F standard oven 35 min. Remove lid. Bake 10 to 15 min. more or until internal temperature reaches 200° to 205°F. Cool in pan on wire rack 15 min. Remove from pan and cool completely. Lightly trim crust on all sides. Cut loaf lengthwise into 3/8 inch-thick slices. (You should get 8 slices.)
Spread 7 bread slices with jam. (Save remaining slice for toast or other use). Cut each slice lengthwise in half to create long strips.
Line bottom of 10-inch cake pan with parchment paper. Forming bread inside pan, arrange 1 strip of bread along inside wall of pan. Lay another strip and continue with more strips around inside of pan until you overlap the first. Continue in this manner until you reach the center. Note: for the final strip, it may be easier to roll up the strip first, and then insert into center of pan. Set pan aside and prepare Custard.
For Custard: Heat half-and-half, milk and sugar in saucepan on medium heat until sugar dissolves. Whisk whole eggs and egg yolks in separate bowl, then whisk into warm liquid until blended. Strain mixture through a sieve, then stir in vanilla. Gradually pour mixture over bread in pan, allowing custard to soak into bread between additions. Let stand 30 min.
Bake in a water bath in 350°F standard oven 55 min. or until internal temperature reaches 165° to 180°F and custard is set. Cool completely in pan on wire rack. Refrigerate until ready to serve.
For Whipped Cream: Stir cream and sugar in chilled bowl of mixer fitted with wire whisk attachment. Sift raspberry powder over cream mixture and let stand 5 min. to hydrate. Whip on medium speed until soft peaks form. Refrigerate until ready to serve.
For each serving: Place 1 slice of bread pudding on serving plate. Top with 1-1/2 oz. Whipped Cream and 5 berries. Serve immediately.