I am holding a VTI position that has unrealized long term gain. I would like to replace this with SPY to use as option collateral (VTI options spread is bad). Is there a way to do so without incurring capital gains taxable event?
Sell VTI futures net short for the amount of shares you own and buy SPY for the same nominal dollar amount.
You could create a fake identity then fake your death leaving your VTI shares to yourself (the fake identity that is). Your inheritance will get a step up in basis so no taxes owed and you could use those proceeds for your SPY buy/write and live to fight another day. Foolproof.
Do correlation analysis of universe of +100,000 international assets and sell short a asset that got 1:1 correlation with VTI. Monitor correlation daily that it doesn't start to diverge. Buy SPY for nominal amount.
Go to an investment bank and ask them to do create an asset swap for you. Swap VTI gains for SPY gains.