Batman started his entire hero’s journey after the death of his parents. That is what made Batman decide he would do everything he could to clean up the streets of Gotham City, although he never really succeeded at that. Not only that, but Batman has never been able to really protect those who trusted him.
Batman has lost even more people close to him, from almost every person who took on Robin’s role to his own beloved mentor and butler Alfred. Commissioner James Gordon also had trouble keeping his loved ones in one peace, with his daughter paralyzed and the love of his life murdered, both by the Joker.
Kate Kane has been a huge part of DC Comics and the Batman world as Batwoman, even leading to a TV series on The CW. However, the original Kathy Kane was Batwoman in the Silver Age of DC Comics for a long time, even retiring for a long time.
She helped Batman and his allies in a war with the League of Assassins, who were working for Ra’s Al Ghul, and they killed her in Detective Comics #485 by Dennis O’Neil and Don Newton.
Tim Drake’s death doesn’t rank higher because it was the most short-lived on this list, as he didn’t actually die. However, the Bat-Family thought he was dead, and it was heartbreaking for them as they sought revenge.
This moment happened in Detective Comics #940 by James Tynion IV and Eddy Barrows. Red Robin was on the ground and told Batman to let everyone know he is sorry and then thanked Bruce before sacrificing himself to save everyone he loved.
Kevin Smith started writing Batman comics and put Bruce Wayne into a strong romantic relationship with Silver St. Cloud. The woman had been around since 1977, but it was when Bruce asked her to marry him that she hit the big time.
This was a strange time in Batman’s life as he was happy for possibly the first time in his life, and he seemed relaxed and was finally ready to settle down. Of course, Smith had dastardly plans, and in Batman: Widening Gyre #6 by Smith and Walt Flanagan, Onomatopoeia slit her throat right in front of Batman.