When Midoriya talks to Yagi about his upcoming role as Kingpin. Yagi points out that the students need to be prepared to go up against real villains who won't take it easy on them, so if Midoriya pushes the Hero team to their limits, it just means that Midoriya is an effective teacher.
The scene with Extortion at the end of the third Observers chapter.
In the days leading up to the Civil War, the villains made sure to take care of their Kingpin.
Near the end, we can see that Aizawa treasures the memories of his stint as Kingpin because, even if he lost, it was also the beginning of a great friendship with the three classmates who stayed with him to the end: Hizashi "Present Mic" Yamada, Nemuri "Midnight" Kayama and Tensei "Ingenium" Iida.
How do the villains decide to celebrate after winning? They go out for brunch, taking their vehicles that Mei had the foresight to ensure were street legal (at least temporarily), and they even invite Extortion to join them!
Con Man performs a Heroic Sacrifice to save Kingpin from a grenade Suneater deflected.
In a way, Kingpin's Break Them by Talking to Izuku, specifically for trying to become a great hero alone.
Before executing her, Forgery encourages her canon self Momo to not stress about being perfect all the time and tells her school is for making mistakes and learning from them.