Originally posted by: manlymatt83
Hi all, posted this in another thread but figured people here would know better:
Wash sales... seems to only apply to losses, correct? So if I am up in my portfolio, and want to pay taxes now on the short term gains I have (to offset some significant short term losses earlier this year), I can sell all of the stock for a $7K short term gain, which will offset a $6K short term loss earlier this year (stupid THMR), buy back the stock within 30 days, and continue holding it, yes?
Here's the two situations I propose:
1) I hold onto the stock that is up now, and it continues to go up over the next few years. Those gains turn into long term gains, and I pay 15% tax. Yet, this year on my taxes, I'll have a $7K short term loss, which isn't offset by anything, so I'll have to wait 3 years (3K + 3K + 1K) to get those losses back on my taxes.
2) I sell the portfolio I have now for $7K profit, completely wiping out the losses I have. I'm in the middle of switching brokerages too, so this would be good because I could move cash and not worry about ACAT. My short term losses (already realized, and no wash rule applies to the losses since I never rebought those stocks back) and short term gains cancel each other out, and I'm left even. I move the cash over to my new brokerage and begin buying again. Yes I lose out on the potential long term gains, but I'm also a bit bearish on the market, and if things drop like crazy soon, I could have even more of a loss to report vs. the potential to break even
Any negatives to #2?
My gut is to sell everything now, to protect myself against the bear market, but also wipe out that $7K loss and start from scratch tax-wise. I may just transfer funds to my new broker at that point (who is going to give me 60 days of free trading) and buy things back.