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This is Motleyful Answers. I'm Allison Southwickwick and I'm joined as always by Robert Brokamp,

personal finance expert here at the Motley Fool. Hi, bro.

Well, hello, Alison.

I hope you're excited for today's episode.

I am so excited.

Here comes the judge. Judge Bro is going to lay down the law and put to rest a few controversial

ideas in personal

finance. Should you try to beat the market? Should you use your Roth IRA as an emergency

fund? Judge Bro is bringing down the gavel of financial justice. We're also going to answer

your question about avoiding capital gains taxes by juggling with your Roth. All that

and more on this week's episode of Motleyful Answers.

It's time for Answers Answers. And today's question comes from Tom. Tom writes,

Hey, fools, I have a big winner in my brokerage account to go along with two big losers.

Let's say I don't see any near-term upside for holding on to the two losers.

Can I make the following move to avoid paying taxes on my winner?

Sell all three positions in the same year, then buy the winner in a Roth IRA.

The two losers would offset capital gains tax while essentially transferring the position

to a Roth IRA that won't get taxed when sold.

I assume there's a holding period where one cannot buy the winner in this scenario to avoid

...