Scottie Pippen probably wouldn't make your "best trash talker" all-time list. Pip is known for many things, but trash talking isn't one of them. But if the point of trash talking is to get in your opponent's head, then a sentence that is crucial to winning a Finals game gets you in the conversation. Scottie is confident he can win the nomination.
“To this day, I think that's the greatest line in basketball. There will never be another Mailman”
Scottie is referring to Game 1 of the 1997 NBA finals. Utah Jazz vs. Chicago Bulls. It's 9.2 seconds to go, the game is tied at 82, and Karl Malone is shooting free throws. This one is in Chicago, so the Jazz had a chance to steal a road game. Malone was a 74.2% free throw shooter in his career and was 3-4 in that game. The Jazz is looking good here. Then Pippen walked by Malone, a.k.a. "The Mailman" and dropped a simple sentence.
“The Mailman doesn’t deliver on Sunday”
This wasn't something Scottie thought of before the game and had in his back pocket. As it turns out, Pippen's brother was in town for the game, and fate would have it Pippen's brother was a postman. Inspired by his presence, with the game on the line, Pip just whispered the sentence to Malone before the free throws. The line worked, as Malone bricked both free throws, and the Bulls got the ball with 7.5 seconds left. MJ got the ball, and I'm sure I don't have to tell you what happened next.
Pip may not have the reputation of Gary Payton or Draymond Green, but if you ranked trash-talking "pound for pound," a six-word sentence that locks up Game 1 of the Finals has to be up there.