Batman began his hero’s entire journey after the death of his parents. That’s what made Batman decide that he would do whatever he could to clean up the streets of Gotham City, even though he never actually succeeded. Not only that, Batman has never really been able to protect those who trusted him.

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Batman has lost more people close to him, from just about everyone who took on the role of Robin to his beloved mentor and butler Alfred. Commissioner James Gordon also had trouble keeping his loved ones in peace, with his daughter paralyzed and the love of his life murdered, both by the Joker.

10 Kathy kane

Kate Kane has been a huge part of DC Comics and Batman’s world as Batwoman, even leading up to a television series on The CW. However, the original Kathy Kane was Batwoman in DC Comics’ Silver Age for a long time, even retiring for a long time.

She aided Batman and his allies in a war with the League of Assassins, who worked for Ra’s Al Ghul, and was killed in Detective comics # 485 by Dennis O’Neil and Don Newton.

9 Tim drake

Tim Drake death

Tim Drake’s death doesn’t rank higher because it was the shortest 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 that he was sorry and then thanked Bruce before sacrificing himself to save everyone he loved.

8 Silver St. Cloud

Silver St. Cloud

Kevin Smith began writing Batman comics and put Bruce Wayne in 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 was very successful.

This was a strange moment 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 cowardly plans, and in Batman: widened twist # 6 of Smith and Walt Flanagan, Onomatopoeia cut his throat right in front of Batman.

7 Thomas and Martha Wayne

The deaths that started it all may not have been heartbreaking for readers, but it was the most heartbreaking moment in Bruce Wayne’s life. The story has been told over and over again. Thomas Wayne was a philanthropist in Gotham City and he was trying to make it a better place.

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One night, Thomas and Martha Wayne went to the theater with Bruce for a family night out. It was the last family night for Bruce, as his parents were shot to death in a robbery, starting Bruce’s journey to becoming Batman.

6 Dick Grayson (Injustice)

The death of Dick Grayson (Nightwing) in Injustice

There were many deaths in Injustice: Gods Among Us. It all started with Joker killing Lois Lane and then Superman killing Joker. This led to Superman taking control of Earth, and then a Civil War between superheroes ensued. This pitted friends and allies against each other and the most heartbreaking death had to be that of Dick Grayson.

Nightwing tried to get Damian Wayne to stop his violence. Damian angrily threw a stick of scrima at Dick, causing him to fall to the ground, where he broke his neck and died instantly. Batman turned to Damian at that moment.

5 Stephanie brown

stephanie brown robin comic book art

The forgotten Robin of the Batman family is Stephanie Brown. He had a romantic relationship with Tim Drake and wanted to be a hero. However, he had a hard time convincing Batman. She eventually got permission to play Robin, but was stripped of the role by Batman when she disobeyed his orders.

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Stephanie wanted to prove to Batman that she was worthy and tried to use one of her long-term plans to clean up Gotham City. In fact, she started a gang war before Black Mask caught and tortured her. In bat Man # 633 by Bill Willingham and Kinsun Loh, went to Leslie Thompkins’ clinic and died there.

4 Damian Wayne

Batman and Robin Damian Wayne

Damian Wayne’s death was tragic because his own mother ordered his death. Damian is the son of Talia Al Ghul and Bruce Wayne and worked as the new Robin with his father.

He was waging a war against his mother and ended up fighting an adult clone of himself in Batman Incorporated # 8 by Grant Morrison, Chris Burnham, and Jason Masters. Talia sent the clone to kill her son, and it was successful, devastating the Dark Knight completely.

3 Alfred Pennyworth

Batwoman Alfred Pennyworth Wayne Manor

Alfred Pennyworth had died more than once, including one when he went into action when he thought Batman was not around. He returned from the grave a short time later and has continued.

However, his most recent death was shocking and he is still dead today. This death happened in bat Man Vol. 3 # 77 by Tom King, Mikel Janin and Tony S. Daniel. His death came at the hands of Bane, who broke the neck of Batman’s mentor.

two Jason todd

The most controversial death, and the most heartbreaking when it happened to Batman, was that of Jason Todd. The story was “A Death in the Family” in Batman # 428 by Jim Starlin and Jim Aparo. Fans voted on whether DC should kill Robin or let him live. Readers voted for him to die, and Joker captured Jason after Boy Wonder’s mother betrayed him.

Joker then beat Jason almost to death and then left him in a building which then exploded. Batman changed his attitude toward anyone playing Robin in the future, and Jason eventually came back to life as Red Hood, never recovering from his own death.

1 Sarah food

Joker kills Sarah Essen Gordon

Sarah Essen was a member of the Gotham City Police Department. She was also the second wife of Commissioner James Gordon. This put a target on his chest. During “No Man’s Land”, Joker was running rampant in Gotham City alongside other villains who almost had free rein with Gotham cut off from the rest of the world.

In Detective comics # 741 by Devin Grayson, Greg Rucka, Dale Eaglesham and Damion Scott, Sarah died. Joker was in a room full of newborn babies. He then released a baby, and Sarah had to choose between the baby and the Joker. She chose to save the baby and Joker killed her instantly.

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