Replace VTI with SPY without incurring capital gain tax?

virw · Dec 23, 2019

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?

El_Cubano · Dec 23, 2019

virw said:
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?

No

ETJ · Dec 23, 2019

Peel of a loss if you have one

bln · Dec 23, 2019

Sell VTI futures net short for the amount of shares you own and buy SPY for the same nominal dollar amount.

luckyfnlou · Dec 23, 2019

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.

bln · Dec 24, 2019

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.

Scataphagos · Dec 24, 2019

El_Cubano said:
No

Occam's Razor.

traider · Dec 24, 2019

Go to an investment bank and ask them to do create an asset swap for you. Swap VTI gains for SPY gains.

Saltynuts · Dec 25, 2019

luckfnlou said:
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.

Freaking GENIOUS!!!!!