Well, you said it was "at best a gamble". I don't know how else I'm supposed to interpret that besides you saying there was "at best" a 50/50 shot of either outcome happening from the perspective of the ones that announced it. I'm going to assume this is not what you meant.
Anyway, since it's established that we're in agreement (maybe? It's not easy to figure out your point of view) that executives are generally able to know with some degree of certainty >50% that their actions will create a specific effect on their stock price. And we also can agree that it is their decision when to announce and execute these actions. It's clearly and obviously a problem that they also are aware of when the stock that they hold in large quantities will be bought and sold.
> Is it a problem? It seems unsolvable if so, unless we should ban CEOs from receiving stock compensation?
If we can agree on the previous bit, then I have no idea why we should throw up our hands and be like "well I guess this is an impossible problem to solve". It's really not. Just be more restrictive with the windows in which executives are allowed to sell. Better yet spread their entire buy/sell order over the course of the year. Or even better still, don't allow them to sell stock AT ALL until they are not in charge or aware of high level decisions at the company.
CEO pay is on average 399x their average employee(https://www.epi.org/publication/ceo-pay-in-2021/). Then, we also allow them to pump their portfolio on a whim at the expense of their employees. I would say personally I don't really care if their compensation suffers, since they've probably already 10x'd my lifetime earnings in their last year of work, and I'd happily switch places with them financially if they're so hard done by.