Can I offset $14k capital gain from stock with a $11k capital loss from bad debit if I claim both in the same year?

Yes.  You get to first offset any gains before taking the 3,000 max loss.

What type of gain, long term or short term?

What type of bad debt are you referring to, business or personal?

Go to this IRS website for bad debt information - https://www.irs.gov/taxtopics/tc453

The capital gain from stock sale would be long term.  The bad debit is personal.  If I dont claim both in the same year I only get to claim the max offset of $3k carry over loss.  So I’m thinking to time both for the same year. Thanks

As noted, you may be able to offset the bad debt against the capital gain, however, we don't have sufficient facts to make that determination.

You need to consider the following:

1. A nonbusiness bad debt must be totally worthless to take a deduction
2. Is this loan to a related person?  If so, this will bring more scrutiny by the IRS
3. While you don't need to go to court and get a judgement, you will need to show that you have taken reasonable steps to collect the debt.  These should be documented and will be asked for should you be audited.
4. You will need to be able to show that this is a bona fide debt and one arising from a debtor-creditor relationship.
5. You must be able to show there was intent of the parties at the time of transfer to create a debtor-creditor relationship.  Was there a true expectation of repayment?
6. While a formal written agreement is not necessary, having this will add credence to the fact that this was intended to be a formal debtor-creditor relationship.
7. The timing of the worthlessness is key.  You need to take the loss (worthless bad debt) deduction in the year it becomes worthless based on the discussion above.  So if you "may" receive some payment in 2022, then you would not be able to take a worthless bad debt deduction in 2021.  You will have the burden of proof to show that the debt became worthless in 2021 to be able to take the deduction.

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@psullivan12 wrote:

If I dont claim both in the same year I only get to claim the max offset of $3k carry over loss.

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Not exactly. It depends on whether the gain occurs before or after the loss. If the gain and the loss occur in the same year, the entire loss will be offset against the gain.

If the loss occurs in 2021, and the gain occurs in 2022, then in 2021 $3,000 of the loss will be offset against ordinary income, and the remaining loss will be carried over to 2022 (if you have no capital gains in 2021). In 2022, the entire carried over loss will be offset against the 2022 gain, not just $3,000. So postponing the gain might be an option for you.

Only if the gain occurs in 2021 and the loss in 2022 or later are you faced with possibly only using $3,000 of the loss each year. Each year the carried over loss will first by offset against any capital gains you might have that year, and then $3,000 of the loss will be used to offset ordinary income.

When I say that the loss occurs in a particular year, I mean that that's the year that the debt becomes completely worthless, as Rick19744 described. You might not have much control over when that happens. You can't just choose to declare the loss in a year that's advantageous for you. When an identifiable event occurs that makes the debt completely worthless, that's the year you have to claim it. You can't claim it in an earlier year if all the conditions to make it completely worthless have not yet occurred. And once all those conditions occur, you have to claim it that year. You can't postpone claiming it to a later year.

"You can't postpone claiming it to a later year"

The debt becomes bad when the borrower decides not to pay.

Since you have to prove that to IRS, that's going to be a later year.

If the explanation makes sense, the IRS will accept it.

bad business debt is different from stock investment that goes to zero.

but even such a stock loss has been successfully claimed in a later year.