Combine the port, juices, and garlic in a nonreactive saucepan. Bring to a boil and simmer until reduced to 1/3 cup. Put the shallots in a stainless bowl, strain the reduction over them, and cool. Add the egg yolk, port reduction, and red wine vinegar to a bowl and whisk to combine. Combine the safflower and walnut oils and drizzle into the yolk mixture, whisking to emulsify. Season with salt and pepper.
TO ASSEMBLE SALAD:
Dress the romaine with the pomegranate-port vinaigrette and season with salt and pepper. Divide between 8 chilled plates. Divide the grapefruit segments between the salads. Sprinkle crumbled Roquefort, then walnuts, and finally pomegranate seeds on top of the salads. Serve immediately.
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