Once South Carolina Republicans came out against the flag, the GOP presidential candidates largely followed suit. But by playing it safe, they forfeited their chance to “demonstrate” that they “care” about African Americans at a moment of deep racial trauma. The presidential campaign has been underway for months now. Yet with the exception of Rand Paul, who has talked bluntly about racism in the criminal-justice system, not a single GOP presidential candidate has done anything bold enough to change the political calculus of a community that consistently votes 90 percent Democratic.

Then, on June 26, the Supreme Court ruled that gay marriage was a constitutional right. If the politics of the Confederate Flag shifted radically over the course of a few days, the politics of gay marriage have been shifting radically over the last few years. Young people, including young Republicans, overwhelmingly back marriage equality. Key conservative writers years ago conceded the fight was lost. Yet not a single major GOP candidate risked alienating the Christian right by endorsing the idea. Instead, they sullenly acquiesced, thus forfeiting another opportunity to redefine their relationship with a group of Americans whose support Republicans desperately need.

But those aren’t the only moments in which the GOP presidential field failed. On June 16, Donald Trump announced his candidacy for the Republican nomination. In recent years, Trump has obsessively questioned whether President Obama was born in the United States and suggested he only gained admission to Columbia and Harvard because he’s black. In his presidential announcement speech, Trump declared that, “When Mexico sends its people, they’re not sending their best. ... They’re sending people that have lots of problems, and they’re bringing those problems with us. They’re bringing drugs. They’re bringing crime. They’re rapists.”

For Trump’s GOP opponents, his comments created a perfect “Sister Souljah” moment, an opportunity to confront the offensive comments of someone on your own ideological side and thus win the respect of those they offend. No one took it. The Republican National Committee called Trump a “high-caliber candidate.” Rand Paul’s spokesperson quipped, “the more the merrier.” Mike Huckabee said, “I personally like him.” Ted Cruz praised Trump’s “experience as a successful businessman and job creator.” Jeb Bush called Trump merely a “rich guy.”

In its autopsy, the RNC called on Republicans to embrace comprehensive immigration reform in an effort to win more Latino votes. More than two years later, not only does every major GOP candidate except Jeb Bush oppose it, but none will even condemn a fellow candidate who slurs Mexican immigrants in the crudest of ways.

The rise of Millennials—who are more ethnically and racially diverse and more secular than any generation in American history—is making America a far more culturally tolerant nation than it was when Ronald Reagan, or even George W. Bush, occupied the White House. For the Republican presidential candidates, that means they’re starting from behind. They begin the 2016 race burdened by their party’s reputation for intolerance, a reputation that becomes more politically costly every year as the result of generational change.