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I don't think the insurance covers you if you are out an out wreckless, I'm guessing it's something where the trainees actions are just that and the insurance fell back on the trainees consent which is why it's worded by the solicitor to say he was pushed into cycling in such a way.
I hope it being in the news a handful of other instructors who have worked with him over the 12 years he has been mountain biking bring out previous bookings.
Clockwise
I wonder if they need to get a court verdict to force the instructor's indemnity insurance co. to pay out.