Olbermann first took his latest shot at CNN CEO Chris Licht, reiterating his claim that when the pair worked together at MSNBC he thought Licht "ate paste", before turning his attention to Tapper.
It marked the first time the 44th President returned to the home since 2017, and Fox News host Greg Gutfeld wasn't excited about the occasion as other in the "liberal media".
"I heard him say 'Media is the enemy of the people' and I'll be frank I thought that was a little too far at the time. I thought to myself that's going too far. I don't know about that. Man, was he 1,000% correct and I was 1,000% wrong."
The company has also appointed a new Board of Directors as it transitions to private ownership. However, its existing management team will remain in place.