How to deal with taxable holdings with large gains

[Bruno]

With my wife still working I am able to fund my ROTH $8000 each year. Can I call Fido and use those funds with a lot of LTCG and tranfer the shares to my Roth?

 

[Texas Proud]

The big question would be how much in in the 22% bracket.... if a lot is there then maybe not as much you can do about it...

I would think about getting rid of as much as possible using the ROTH as that is saving 22% on all withdrawals... but if your regular IRA is huge then RMDs will hurt you in the future...