This is why people get busted for insider trading so often. They thing obscuring the purchase slightly will get the SEC off their tracks. Nope.

Even if you had a long-lost friend do it, the big trigger is the purchase itself. Someone buys no options in the past 5 years, suddenly buys a ton of out-of-the-money call options 2 days before a merger. The SEC zeros in on that like a laser.

Then they look at who purchased it. Any connection to the company that acquired/was acquired? No? Do they know anyone who is? Let's get their phone records.

I also think the SEC knows they can't police every transaction, so the ones that are flagged get investigated hard, to make an example of them.

If you really wanted to obscured it, one way would be to have a trail of purchases such that the "big one" doesn't look out of place. However, that would mean you'd need to make a bunch of losing bets.