Assignment risk. Apple may as well go up another 10-20% and someone may decide to execute on ex-dividend. Deep ITM have very little extrinsic value. @scott is trading options so he may be the right person to ask.

If I’m, say, holding AAPL, and I’m looking at these charts and agree we’re coming up on a big bear market (say, per @rsotc‘s video, a ~60% pullback to the uptrend line around $70)…would it be crazy to sell long-dated, deep ITM covered calls (stay, with a strike price of $70 or so), with the goal of realizing profits but not letting go of the shares? You could then either let them expire worthless (if you somehow manage to time it really well) or just buy-to-close at a steep discount.

Why is that a bad scheme?

Obviously, if you’re wrong about the bear market, you’ve capped your gains and tied up your capital for a long time—especially if it goes on a serious bull run. And then there’s the tax consequences of the calls likely being short-term gains verses selling the shares for long-term gains.

Am I missing something else?

NIB (cocoa ETN) has pulled back to minor uptrend line support & with just about all commodities in solid uptrends, I think a decent case for an objective long entry here stops somewhat below can be made. /CC (cocoa futures) is also trading just above the 2370ish support level as well.