Faster draw *Spoilers*
I can't believe Harlan beat Wade to the shot even though Wade already had his gun drawn, cocked, and aimed. Also consider that Wade is currently a police officer, miliarty background, and an avid gun collector. He had the advantage.
If I was Wade I would of shot Harlan on first sight. In the face. I mean he did shoot your daughter, lied to and kidnapped your son, and shot at you.