On gay rights, Trump has been more open to following the liberal drift in American culture.
He has not railed against same-sex marriage, as other Republicans have, and said in the "Today" interview that North Carolina should have not passed a law regulating which bathrooms transgender Americans use.
Obama, in contrast, has suggested that if he had a son, he would be reluctant see him play football, and has defended Black Lives Matter activists.
Hillary Clinton, in a tweet, wrote, "A woman, a leader, and a freedom fighter. I can't think of a better choice for the $20 bill than Harriet Tubman."
Politically, Trump's remarks suggest he will continue to appeal to voters, particularly whites, who feel left out of Obama's vision of America, Gillespie said adding that he will have to pivot for the general election.
Trump's approach may be resonating.
A recent Pew Research Center poll found that 46 percent of Republicans said the country's increased diversity makes the U.S. a "better place," compared to 13 percent said who that diversity makes it a "worse place," and 39 percent who said "no difference." The majority of Americans (59 percent) indicated "better place."
In the poll, Trump supporters, compared to those backing the other four presidential candidates, were the least likely to say "better" (39 percent) and most likely to say "worse" (17 percent).
Ultimately, the rhetoric over placing Tubman on the $20 is about a different kind of political currency, one of identity, political experts say.
"That's going to symbolize for them a kind of change they are not necessarily comfortable with," Gillespie said.