This was the dish that was on menu listing for the 1960s/70s bash held earlier this year. I ended up not using pancetta because I saw some Capicollo from Niagara Food Specialities. It fitted the origin idea better.
The taste that I wanted people to remember is the old fashioned baked ham with pineapple rings. Originally, the idea was to crisp up rounds of pancetta and serve caramelized pineapple on top. As the responses grew to the invitation list, the original execution of freezing then cutting and frying the bacon seemed a little too fussy especially if the dish was to be served warm. So, the more traditional ham idea came back on the table but rather than be too literal -- put pineapple on ham and bake -- I decided to caramelize the pineapple, cool, then wrap the capicollo around the pineapple and hold in play with a toothpick.
The presentation was ugly and in fact, it was the last dish on the appetizer course to be tried by anyone. It lacked beauty but it was easily the dish that most people loved. This was largely due to the Pingue's ability to turn the magical pig creature into a salty silky piece of love.
Once again, this is not so much a recipe as finding the right flavours to put together. The only real cooking was the pineapple. Just chop pineapple into pieces that can be wrapped by the ham. Take the pineapple and place into a pan with a sprinkle of sugar. Use the most flavourful available. I used brown but palm would be better and white will do. Cook the pineapple on medium heat until sugar melts and caramel process begins. The time will depend on the juiciness of the pineapple but when the sauce is sticky and brown and burns your skin when touched, it is done.
Be careful when cooling. I didn't leave it outside the fridge for long enough and condensation built up and watered down the flavours. Once it is cooled then put in fridge. Also, just a small tip, raw pineapple breaks down meat and can change the texture. This is the same reason that raw pineapple cannot be used to make gelatin using animal gelatin. To play it safe, wrap your pineapple just before the party starts. (That's what she said.)
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