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I'm looking at about $88k in short term capital gains for 1999 (a tax liability of $35K) and I am searching for some innovative ways to “push” these gains out to 2000. I have provided some of my own ponderings below and would welcome any discussion on these strategies or, hopefully, even better strategies for reducing my 1999 capital gains tax exposure.

Sorry bud, neither of your approach make sense.

For both method, you're basicly trying to give your realized gain away (through re-investing and hoping for losers). Make about as much as (tax-wise & financially-wise) as loaning a stranger x amount and have that stranger never pay you back. Remember, a $35,000 loss will only translate to a federal tax liability reduction of about $11,000. That's still a lost of about $24,000.

To be financially smart, pay your taxes and enjoy your windfall.
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