Donald Trump, the King of Twitter, has had plenty to say about Fox News anchor Megyn Kelly. He has accumulated 117 tweets in his Kelly archive since 2011. At first, they were professional and appropriate.

My @FoxNews interview with @megynkelly discussing the 2012 election and the Newsmax-@iontv debate http://t.co/TotTpvNZ

— Donald J. Trump (@realDonaldTrump) December 12, 2011

"@megynkelly: #KellyFile behind-the-scenes: Here I am with @realDonaldTrump on set! He joins me at 9p ET – tune in. pic.twitter.com/QUVZt6NceC"

— Donald J. Trump (@realDonaldTrump) March 23, 2015

But then came that infamous Fox News debate of August, 2015, when Kelly started off by asking Trump questions about his misogynistic attitude towards women.

And it was all downhill from there.

Here are the ten worst tweets that Trump has leveled against Megyn Kelly since then. I had a really difficult time limiting my list to just ten.