Except he’s not picking against the spread. He’s picking winners and the first team he lists is the one he picks to win. He provides his prediction of the actual score as well and notes the spread for reference. I think it would be easier if he consistently showed the spread as (-x) on the favorite instead of seemingly arbitrarily flipping the sign and putting it next to the non-favorite. Ideal example from that same pick would be: PITTSBURGH (-3) 28, Cincinnati 27.
In the second example you provided, he’s picking the Bears (I think, don’t have the article up) to win and the score to be 20–17 (not totally absurd, a lot of analysts guess the score, they’re wrong 99% of the time but it’s fun haha), which given the spread of -3 would in fact be a push.