Generally true. However, he precedes it by saying, "That poor guy...."
I'm not exactly stretching things to infer he's familiar with the man and his condition.
Oh, for God’s sake, can’t you interpret in another way? The poor guy - sitting around his computer in his pajamas hoping against hope to get another freelance gig - is suddenly in the news and Trump is talking about his article. He jumps up, hysterically - undoubtedly his arms flailing in distress - and says “Oh, no! Poor me! How did I get into this mess. I hate Trump!” And that’s why he is a poor guy, a schlub, and a putz.