West first talked about his decision to wear one of Trump's now-infamous Make America Great Again hats back in April, explaining that it was more a message of self-empowerment than it was a political statement.
"As a musician, an African-American, a guy out in Hollywood… everyone around me tried to pick my candidate for me, and told me every time I said that I like Trump that I couldn't say it out loud or my career would be over or I'd get kicked out of the black community," he shared. "Because blacks, we're supposed to have a monolithic thought, we can only be Democrats."
West recalled that he first expressed his support for Trump before being admitted to the hospital in November 2016, reportedly for an unspecified mental breakdown -- and when he came out, he'd lost his confidence.
"It took me a year and a half to have the confidence to stand up and put on the [MAGA] hat, no matter what the consequences were," West shared. "What it represented to me was not about policies, because I'm not a politician like that, but it represented overcoming fear, and doing what [I] felt, no matter what anyone said, and saying, 'You can't bully me. Liberals can't bully me, news can't bully me, the hip-hop community can't bully me."
"Because, at that point, if I'm afraid to be me, I'm no longer Ye. That's what makes Ye," he added, before admitting that he actually enjoys "when people actually are mad at me about certain things."
West then went on to pontificate on the "motivating forces" in the world: namely love and fear, and how people are always "pushing out so much hate."
"[But] love can cure so much," he said. "When I see people just go at the president, I'm like, 'Why not try love?'... One by one by one, we can defuse this nuclear bomb of hate that we're in as a society by thinking of everyone as our family, and how we treat our kids."
"I think that's a beautiful thought, but just in literal terms, there are families being torn apart at the border of this country… as a result of what this president is doing. And I think we cannot forget that, whether we like personality or not, his actions are really what matter," Kimmel countered. "You so famously said, 'George Bush doesn't care about black people.' It makes me wonder what makes you think Donald Trump does, or [cares about] any people at all?"
West was speechless for the first time during the interview as he carefully considered his response, or perhaps was considering Kimmel's point maybe for the first time.
Unfortunately, fans won't ever know how the star would have responded because his silent contemplation went on for such a long beat that Kimmel needed to throw to a commercial break.
Kardashian West joined the talk show host on July 30, and opened up about her high-profile visit to the White House, where she successfully petitioned Trump to grant clemency to Alice Marie Johnson, a 63-year-old inmate who had been serving life without parole for a first-time, non-violent drug offense.
Kimmel asked West about his wife's White House visit, and jokingly inquired if he was worried about her "being alone in the office with President Trump."
"Well, he is a player," West quipped with a smile. The joke is particularly pointed (perhaps unintentionally), considering Trump's multiple alleged infidelity scandals with women such as adult film star Stormy Daniels and former Playboy model Karen McDougal.
One particularly telling remark came when Kimmel asked West if he'd ever regretted anything he'd said or tweeted. The rapper responded, "I think people focus too much on the past, and focus too much on regret."
According to West, having the confidence to make a remark, whether you eventually change your mind or reconsider your position, is better than censoring yourself out of a fear of what other people will think. With that often comes push-back and repercussions, but sometimes it's OK to get hurt.
"We [as a society] are too protective. We always don't want someone to get hurt. Can you imagine me talking to my publicist when I said I was going on TV again?" West said, laughing. "I'm going on TV because it's awesome."