1) Possibly, unless there is an exception.
https://www.irs.gov/publications/p515#en_US_2020_publink100015245
Income Subject to Withholding
This section explains how to determine if a payment is subject to Chapter 3 withholding or is a withholdable payment.
Amounts Subject to Chapter 3 Withholding
A payment is subject to Chapter 3 withholding if it is from sources within the United States, and it is fixed or determinable annual or periodical (FDAP) income. Generally, excluding gains but including certain gains from the disposal of timber, coal, and iron ore, or from the sale or exchange of patents, copyrights, and similar intangible property.
In addition, a payment is subject to Chapter 3 withholding if withholding is specifically required, even though it may not constitute U.S. source income or FDAP income. For example:
>>"corporate distributions may be subject to Chapter 3 withholding even though a part of the distribution may be a return of capital" or capital gain that is not FDAP income.
