Down $150k on CC's. What's the risk of exercise on deep ITM CC?
u/not_a_cumguzzler ·
Reddit — r/thetagang
· May 06, 2026 at 19:16
· ⬆ 22 pts
· 💬 50 comments
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I can't roll out of these deep ITMs into OTM CCs unless I roll like 3 years out, which I'm not sure I want to do.
If i continue rolling into basically the same strike, one month out at a time, hoping for a pull-back to exit my CC (or roll for further up/out), What are the chances that the CC gets exercised? Ex-dividend is coming up June 8th. I'm thinking of rolling to the June 18th CC's today or in the next few days.
Backstory:
Never really intended to sell, was trying to generate some income and the dumb perma-bear in me feared the correction last month was gonna turn into a bear market. Sold CC's at the bottom, then GOOG went on to have its steepest rally in history (and it's still going). Don't really want to take the tax hit and have to pay 20% federal + 13% state taxes.
I used to work for google, got these shares are part of compensation, then i quit and wanted to try to semi-retire in asia (I'm single af, kind of a loser with lots of issues and now this is messing up my mind even more). This is pretty much all the life savings I have (blew the rest on hnd-jobs and blow and AMC. Mainly AMC, including my 401k)