Tax planning and the question of when and whether to tax capital gains have been complicated with the American Taxpayer Relief Act of 2012, which introduced a new top 20% long-term capital gains tax rate and 3.8% Medicare surtax on portfolio income, writes Michael Kitces. There are now four capital gains tax brackets to consider as a result. Kitces discusses various scenarios under these brackets, noting that the old rule of thumb of deferring capital gains as long as possible no longer applies in all cases.