Hall of Fame running back Jim Brown, who has previously discussed issues facing the African-American community with Trump, the President's daughter and adviser, Ivanka Trump, and her husband and White House adviser Jared Kushner, were also in attendance.
"Topics of discussions will include manufacturing resurgence in America, prison reform, how to prevent gang violence, and what can be done to reduce violence in Chicago".
Before they adjourned for a roasted chicken lunch, Kanye stood up, walked over to Trump and gave him a bear hug.
Over a lunch of caprese salad and roast chicken, Gidley said discussion would be centered on "President Trump's historic work to benefit all Americans". "That was quite something", Trump said.
It was the first of several off-color remarks Kanye would drop in the Oval Office, including this line: "He might not have expected to have a insane motherfucker like Kanye West run up and support".
"Watching this today, the only thing I could compare it to was Tom Hanks talking to Wilson the volleyball", Kimmel said.
West also used the opportunity to applaud Mr Trump's efforts with North Korea and said he liked the country.
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"I met with Michael Sacks, that's Rahm's right-hand man", West said, referring to Rahm Emanuel, Chicago's mayor.
He revealed that his friends had tried to scare him not to wear the MAGA hat, popularised during the president's campaign in 2016.
Georgetown University professor Michael Eric Dyson sounded off on Kanye West's visit to the Oval Office. I have conversations that basically said that welfare is the reason why a lot of black people end up being Democrat.
Mr Trump said: "That's really nice".
The rapper, who has broken ranks with much of the left-leaning entertainment industry to come out in support of Mr Trump, even said he could be president himself - but "only after" Mr Trump in 2024.
He said that his dream was to have both Trump and Colin Kaepernick wearing a "Make America Great" hat.
West also had a sartorial suggestion for Trump, proposing a hat that says just "Make America Great" - dropping the "again".
"I love this guy right here".