It may be that he was towing the boat by a bridle attached to just the forward towing points, rather than a four-point bridle, that puts most of the load on the aft attachment points. Doing so puts a lot of strain on the two points that can't afford it, and will also tend to submerge the bow. Not really a bright way to tow an inflatable. Also, towing one with an outboard still attached, in heavy seas is just asking for trouble.
The other thing that could have happened is that the painter could have snapped. Many dinghy painters are made of polypropylene, and polypropylene is extremely sensitive to UV degradation. If the painter hadn't been replaced or inspected recently, it may have snapped under the strain of towing a swamped dinghy in heavy seas.
There is a large sloop, at least it appears to be a sloop, in New Bedford harbor that is moored and has only a stub left of the mast. Very sad to see. Most of the boats that end up in trouble in storms like the one that just came through are due to a lack of diligence and attention by the owner.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.