You read stories about people exploiting legal loopholes for...

You read stories about people exploiting legal loopholes for personal gain all the time, at the time they think they're quite clever but usually it backfires on them.

At this stage it looks to me like Bolton saw the put option as a low risk play to squeeze something out of BCS. He entered into these put options before he purchased BCSCA shares. He might have thought that technically speaking he has no liability until date xxx, etc, according to the wording of the contract. But as usual it turns out this clever little 'strategy' has brought more trouble than its worth.