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I think it was almost certainly a stingray. I live about a mile from there and have seen quite a few monster ones while snorkeling in 5 to 10 feet of water. They look bigger than me without the tail. The shark story is interesting. I've never seen one in the sound but have heard of them being spotted by boat anglers. The 8-inch fin sticking out of the water could have been that of an ocean sunfish. They're around, and although they are filter feeders, one could have run into your line, though that seems much less likely than a stingray (or are they giant skates?). I doubt there's a striper alive that could dump 220 yards of 30-pound line on the outfit you describe assuming a firm drag. Even in that unlikely event, it would probably happen in much less than 25 minutes, an amount of time that also points to a slower moving creature like a ray. Neat stories.
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