You will win all three items. The CGC 8.0, 1990 Donald Trump Playboy magazine. The 2016 JSA Autograph Media Donald Trump Signed.
And the 1989 BGS 9 Rotten To The Core #26. You will win the very rare Donald Trump Autograph signature on a Media or Press Pass/ badge from Georgia. Media and Georgia are two rare traits for a Trump signature/autograph.
For him to sign a media pass during his run for office is incredible. Think about his relationship with the media and phrase fake news.