It's not always easy taking on the role of a sidekick, let alone the partner of the Dark Knight in the meanest city in the DC universe. Batman has worked with a few different Robins, and has placed the same pressure and responsibility on each of them – sometimes leading to mistakes.
The Boy Wonder progressed to Teen Wonder and even the Girl Wonder later on in the Dynamic Duo's history, but each character has had to compare their greatest victories to their darkest losses.
10 Dick Grayson Was Beaten By Lady Shiva On One Of His First Missions As Robin
After the murder of Dick Grayson's parents, the mourning young boy began his vigilante career in the hopes of finding their murderer long before he met Batman. He began his training with Batman and slowly created the armor and identity of Robin, though he was forbidden to go on missions.
However, when Batman was poisoned in a battle with Lady Shiva, Grayson put on his costume for the first time and left the Batcave to help free Batman. Unfortunately, he was quickly defeated and beaten by Lady Shiva, who decided to let him live and even offered to train him better than Batman.
9 Tim Drake Was Unable To Help Azrael When He Took Over As Batman
One of Batman's greatest failures saw him suffer a devastating back injury in a climactic battle with Bane during the "Knightfall" storyline. This forced him to pass the mantle of the bat on to someone new while he recuperated. Bruce chose Jean-Paul Valley/Azrael and enlisted Tim Drake/Robin III with aiding and keeping tabs on the new Batman.
Unfortunately, the mental programming that made Valley fit for the mantle also began to push him over the edge. Tim Drake struggled to keep Azrael under control as he developed increasingly violent tactics, leading to a fight between the two. The death of Abattoir at the hands of Valley was another death on his conscience and finally forced Tim to contact Bruce Wayne.
8 Dick Grayson Was Fired By Batman After Spending Too Much Time With The Teen Titans
Batman's rules for Dick Grayson when he debuted as the Robin were incredibly strict. As Grayson got older and more experienced, he acted on his own, which caused a rift between the Dynamic Duo.
After being harshly reprimanded by Batman due to Grayson's increasing levels of commitment to the Teen Titans, he was fired as Batman's partner. This ultimately pushed Grayson to create his own identity of Nightwing, but it tainted his relationship with Bruce Wayne for years.
7 Jason Todd Let An Abuser Fall To His Death Against Batman's Wishes
Batman quickly replaced Grayson with a street-wise kid named Jason Todd, who had been caught trying to steal the tires from the Batmobile. Jason had a tough attitude that initially made him a great choice to take over as Robin, though he quickly began to disobey Batman's orders.
Robin apprehended a man assaulting a woman who was then freed due to diplomatic connections. Jason headed to the abuser's apartment on his own and seemingly pushed him off the balcony to his death, which he lied about when asked by Batman. While Jason might not consider it a failure, this possible murder was definitely a failure by Batman.
6 Damian Wayne Was Manipulated By Nobody, Who He Then Killed In Anger
Morgan Ducard was the son of the assassin who helped train Bruce Wayne on his road to becoming Batman. Ducard trained alongside Bruce Wayne and developed resentment toward him, which led him to create his own costumed identity known as Nobody.
He began to manipulate Damian Wayne/Robin into following his assassin training by killing his enemies in an attempt to drive a wedge between the Dynamic Duo. After Nobody was defeated, Damian Wayne decided to kill the villain so he wouldn't be able to come after them, which was witnessed by Batman and served to cause a number of issues in their relationship.
5 Tim Drake Nearly Quit After He Failed To Save Young El From Drowning
The third Robin began operating on his own following the "Knightfall" saga. This allowed Tim to tackle street-level crime that brought him into conflict with a criminal known as Young El who had been responsible for the shooting death of one of Drake's high school friends.
When Robin attempted to capture Young El after a failed gun deal, the young gang member was trapped under a collapsed beam in a building that was filling with torrential rainwater. Robin was unable to lift the collapsed beam, and Young El drowned. This failure caused Tim Drake to quit as Robin for a short period of time.
4 Two-Face Forced Dick Grayson To Let A Man Die So He Could Save Batman
After Grayson spent a year fighting alongside Batman, he was forced into a confrontation with Two-Face that would lead to his greatest failure in the Robin costume. When the Dynamic Duo was captured by Two-Face and forced into a fake trial, Grayson was forced to choose between saving Batman or a judge who was hanging above two trap doors.
Robin attempted to use Two-Face's dependence on his coin to save both men, but he was tricked and the judge fell to his death. Two-Face then viciously beat Robin with a baseball bat until Batman was able to break free from his bonds, take down the villain and his goons, and save Robin.
3 Damian Wayne Was Killed In His Final Battle Against The Aged Clone Heretic
The current Robin is Batman's son Damian Wayne, who was raised by his mother Talia al Ghul and trained in the League of Assassins. When he chose to live with his father instead of Talia, she set in motion plans to bring her son back to her. She also created a clone of Damian Wayne that she artificially aged into an adult and named Heretic.
When Batman and Robin attempted to stop Talia and Heretic's plans, Damian Wayne was forced into a sword fight with his older clone. Unfortunately, he was no match for Heretic and he was stabbed through the chest and killed. Batman was eventually able to bring Damian back to life but it still stands as his biggest failure.
2 Jason Todd's Search To Find His Biological Mother Ended In His Death
The second Robin's violent tendencies and impetuousness soon led to him fracturing his partnership with Batman, and Jason Todd was sidelined in the Batcave. However, he soon discovered a mystery about his biological mother that he began to investigate which took him overseas. Batman soon followed and attempted to aid him in his search.
After Jason discovered the identity of his mother, he left on his own to find her. He was betrayed and captured by The Joker, who brutally beat Robin with a crowbar before leaving him in an exploding warehouse to die with his mother. While Jason eventually returned, this still stands as the character's greatest mistake.
1 Stephanie Brown Was "Killed" During Her Attempt To Win Back Batman's Trust
When Tim Drake had quit as Robin, his close friend Stephanie Brown/Spoiler was offered the role of Robin to become the first Girl Wonder. Her time in the role was short-lived as she was quickly fired by Batman after disobeying orders and helping him stop an armored villain named Scarab.
Hoping to win back Batman's trust, Stephanie attempted to launch one of his plans to bring Gotham's gangs under Matches Malone's control, but she messed up when she didn't realize that Malone was an identity used by Batman. Steph was captured by Black Mask, who tortured her until she later died. It was later revealed that she survived and returned to become the new Batgirl.