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Preheat the oven to 375°
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Arrange the pineapple, halved ripe tomatoes (skin side up), garlic cloves (unpeeled!), onion, and jalapeno (skin side up) in an even layer on a large baking sheet.
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Bake for 10 minutes on the upper rack of your oven. Then turn the oven to high broil.
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Broil for 8-12 minutes, or until the tomatoes and jalapenos have blistered and blackened pretty thoroughly on top. The Pineapple chunks should also be slightly burnt.
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Remove pan from the oven, and let cool for 15 minutes.
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Peel and discard the skin from the garlic cloves.
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Transfer the garlic, onion, and jalapeno to the bowl of a food processor or blender. Reserving the pineapple chunks and the tomatoes. Add the handful of cilantro (if desired) the Lime juice, salt, and cumin.
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Pulse the garlic, onion, and jalapeno mixture until it is finely chopped.
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Add in the tomatoes and the pineapple and pulse until fairly blended, but some small chunks remain.
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You can serve this slightly warm or chilled. It is equally good either way.