Yes, that's very easy! Let me count the ways. First of all, Obama's daughters are much more likely to be murdered, abused or falsely accused by police than they would be if they were white. Even iconically famous black people are sometimes mistreated by police officers who don't recognize them. I'd say being at a high risk of murder counts as a disadvantage! I don't even need to draw a line back to ancestral violence for that one—that's just regular old present day violence.
Second, although the Obama sisters enjoy substantial family wealth due to their parents' incredible achievements, the fact that they were born black means that, statistically speaking, they would have been far wealthier if they'd been born to a comparably wealthy white family. For example, if the Obama's are the X richest African American family, they'd be far richer if they were the X richest white American family. Bingo! Disadvantage! Why does that wealth gap exist? There are many recent crimes, many tied to violence, that exacerbated the situation. But we can start by looking at the fact that Black people, including Obama ancestors, were violently forced to build wealth for white people without any compensation.
There are many more ways in which contemporary American society puts extra pressure and psychological burden on African Americans, yes even rich African Americans, all of which can be traced back to historical violence in our history, and all of which clearly affect the outcomes we associate with "success."
Whether you admit it or not, you're arguing that the person who "deserves" to win in our economy is the person whose ancestors perpetrated horrific crimes against his competitor's ancestors and who doesn't have to face the constant daily effects of ongoing racism in our society.