Batman may have been a loner for the majority of his life, but just because he dealt with the tragedy of loss at a young age, does not mean he doesn't want a family again. However, his greatest fear is not giving into his urges to eradicate Gotham's most devious villains, it's losing the ones he loves and feeling that pain all over again. Alfred was Bruce's surrogate father for the longest time, before and after he started training, and has always been the loving father figure he's needed across all incarnations. After Bruce became Batman, he took in young Dick Grayson, and helped him cope with a similar loss he felt as well. Thus began the first of the Bat-Family, Gotham's most well-known heroic vigilante group.
Like all families, tragedy will strike, and everyone will come down with a bad case of heartbreak. Across the multiverse of DC Comics, there have been plenty of examples of tragedy but today, we will be focusing on the rough times that Batman seems to bring along with him whenever he gets close to someone. Although it seems like nothing phases him when he's on the streets of Gotham stopping crime, Batman is still human and the most effective way to get to him would be through those around him. This particular list will also be focusing mostly on the source material and moments in the main continuity, so alternate realities such as Injustice won't count. This also disqualifies TV shows such as Batman: The Animated Series or Justice League, as they deserve a list of their own. Before diving in, it's best to keep those tissues handy.
20 THE END OF JASON TODD
Jason was the second Robin, and as such, was treated like a son to Bruce Wayne. Like the former dynamic duo, Jason suffered tragedy and loss like both Bruce and Dick before him had. Unlike them, though, Jason grew up in the harsh conditions of the criminal underworld. The first indication of this was when he was caught trying to steel the tires off the Batmobile, to which Batman intervened, and applied the same method he had with Dick.
Thus, the second Robin was born. However, at one point the Joker escaped from Arkham Asylum and ended the life of Jason Todd. However, his true fate was left up to the readers, if they called a certain phone line to determine whether or not Jason lives. The rest, is history.
19 DICK GRAYSON QUITS
It seems as if Dick Grayson was everybody's favorite Robin. He was compassionate, acrobatic, full of youth, and the perfect foil to Batman's personality. Most importantly, however, was that the Joker didn't single him out in any way, but that doesn't mean he wasn't without his personal tragedies.
At one point, Batman and Robin had a falling out. Dick felt as if he was being pushed away, or considered as below Batman, and not a hero in his own right. Also, it could also have been because Dick didn't want to be like Batman, and live in a grim, foreboding world. When Dick left to become Nightwing, Batman felt truly alone, and thus made him take in Jason so hastily.
18 BARBARA GETS PARALYZED
Barbara Gordon wasn't raised out of tragedy, unlike the previously mentioned candidates. However, during one of Joker's infamous escapes from Arkham Asylum, he tracked down Commissioner Gordon and his daughter, and made them both endure great pain just to make a statement.
For Jim, it was that his daughter was paralyzed from the waist down. For Barbara, it was that she could no longer be Batgirl, and go through years of depression afterwards. In the New 52, she recovered from her injury, but before that timeline occurred, she became the information broker known as Oracle. She once said that she endured many nightmares of that one night.
17 DAMIAN VS BATMAN...?
Damian Wayne is a rough kid, due to the fact he was raised by Talia al Ghul and the League of Assassins, making him a ruthless 10-year old fighting machine. Damian became the new Robin under Batman's tutelage, and to say that is was a rocky experience would be an understatement.
Damian wasn't just reckless, he was overly-aggressive, constantly struggling with the difference between justice and vengeance. At one point, Joker returned to Gotham after a year of absence, and forced Robin to fight his own father -- or so it would seem at the time. Damian, in tears, stated he would rather let his father end him by his own hand than by Damian's, indicating his change of heart.
16 DAMIAN'S END
In comics, nobody truly goes away forever, but that does not mean the story won't pull at anybody's heartstrings, as was the case with Damian Wayne's final moments. During a battle with the Heretic, an adult clone of Damian, Nightwing and Robin were defend Wayne Tower. They were reminiscing of their times as Robin which, any comic book reader will know, is a sign that something wicked is coming.
When the Heretic arrives, the battle ensues. Heretic incapacitates Nightwing, while Damian is forced to bravely fight him alone. The result, is heartbreaking, as Damian loses his life in the ensuing battle. Later on, Damian's funeral is held next to Bruce's parents, where they lie.
15 THE RED HOOD
Jason Todd, luckily, was revived at one point in the comics, due to the infamous Lazarus pits that Ra's al Ghul is most familiar with. The side effects include temporary madness, however, or at the very least it can cause mental instability. This is exactly what happened to Jason as he adopted the Red Hood persona and became a terror on Gotham, eventually forcing a confrontation with Batman.
Jason explains that he forgives Bruce for not saving him from Joker's wrath, but despises him for granting him mercy thereafter, since he took Jason away from him. Batman still sticks to his moral code, but at the expense for any respect or love that Jason had left for him.
14 BATMAN'S ORIGIN
We all know the story of the young orphan rich boy who watched his parents get gunned down in front of him, starting off his guilt-ridden quest to rid Gotham of its criminal underworld. Unlike everyone else in the world (who receive therapy and support from other relatives or friends), Bruce goes to the extreme by training himself extensively through body and mind to the absolute physical peak of human condition.
Every Batman story ever told always hammers-in this immaculate guilt he feels since that moment, implying that he will never get over the end of his parents lives, and this is what fuels him on his mad crusade.
13 DICK GRAYSON'S ORIGIN
Dick was raised in a circus, with his parents being the top-tier acrobatics in play, a trait he carries with him to this day. However, the mob boss ends up taking their lives by sabotaging their act in front of a crowd, and more importantly, in front of their son.
With no family to turn to, or even the circus having no rights to raise the boy, Dick was truly alone, and if anyone can understand how that feels, it's Bruce Wayne. Bruce took him in as a foster son, and eventually as a partner, Robin. Not so that he could become like Batman, but so that he wouldn't end up as depressed like him.
12 TIM DRAKE LEAVES
Tim Drake was the Robin who reminded Batman why he needed a partner, since he was depressed for a time because of Jason's passing. Tim was a brilliant detective, as he proved it by deducing Batman and the original Robin's true identities as Bruce Wayne and Dick Grayson, a more astonishing feat since he was a young boy at the time.
During his teen years, Tim's father finally discovered what was going on, and immediately acted on his instincts as a parent. He drove down to Wayne Manor to confront Bruce and Tim, eventually forcing his son to drop the mask and step down as Robin.
11 THE LETTER FROM THOMAS WAYNE
During the events of the Flashpoint, Barry Allen was given a letter to him by Thomas Wayne, to give to his son Bruce in the dimension where Barry came from. You see, in that particular universe at the time, Martha and Thomas Wayne survived that night in the alley, but Bruce did not.
Thomas went on to become Batman in that universe, while in contrast, as we know, Bruce became Batman in the other. This letter was supposed to be a heartwarming message from a father to his surviving son. However, at one point Eobard Thawne takes the letter that meant so much to Bruce, and rips it to shreds in seconds, as if it were nothing.
10 THOMAS WAYNE TELLS BRUCE TO BE HAPPY
Around the events of the last entry on this list, Bruce does manage to meet with his father at some point in the alternate universe. However, that universe is falling apart, so Thomas pushes Bruce into the Flash and tells them to get to safety, but not before he gives his son the advice he wasn't expecting, but didn't know he wanted.
Thomas tells Bruce that there was more in the letter he wished he could have shared, that he wants the sad life of Batman to end with him, and he tells Bruce to not be the Dark Knight. Instead, he tells him to find happiness in life and be the father that Thomas could not be for his son.
9 NIGHTWING WAS SUPPOSED TO BE A TALON
During the "Court of Owls" storyline, Bruce finally escapes the wrath of the Court, and returns home to the Batcave, much to the relief of his family. However, Batman is now broken, wired, and extremely volatile with his added instability, due to the hardships he endured from his captivity.
Alfred had captured the Talon, an assassin for the Court, and kept him in stasis in the cave, giving Bruce the opportunity to do his detective work. Dick walks in, and begins to converse, and it eventually becomes a loud discussion until Bruce ends it by revealing that Dick was supposed to be a Talon as well, had he not taken him in before the Court of Owls got to him first.
8 BATMAN AFTER JASON'S PASSING
The end of Jason Todd, as stated many times on this list, was a pivotal moment because Batman blames himself for recruiting the boy into this line of work, to which he will continue to do to this day. After those horrible events, Batman no longer acted as a detective, more so like a bruiser, constantly thinking with his fists.
One time, he recklessly got himself severely injured to the point that Alfred had to keep him on a bed for a long period of time. More importantly, when Two-Face resurfaced in Gotham, there was a hostage situation involving two boys, and Batman accidentally addressed one of them as Jason. This all showcases a dangerous time for him to be Batman.
7 JOKER MANIPULATING JASON'S LIFE
The Joker loves nothing more than to torment his arch nemesis, the Batman. But even more that that, he loves to make him suffer by targeting those he loves with even more pain. It was revealed that the Joker manipulated the life of Jason Todd from the start, from his rocky lifestyle in the slums of Gotham, to his removing of the tires on the Batmobile.
He even knew that Batman would take him in, knowing the Dark Knight couldn't resist having a partner again. All for the express purpose so that he can take Jason's life and make Batman miserable again, just the way he likes him.
6 ENDGAME
In the "Death of The Family" storyline, Joker has returned to Gotham after being gone for a year, and his shadow of terror has spread wider than ever before. Joker believes that Batman has become too sentimental and soft because of his relationship to his new family, so he makes it his mission to make Batman suffer again, so he can get things back to the way it used to be.
He captures them all, and towards the end, makes it look like he attacked them to prove a deadly point. Luckily, it was all a bluff, but it's still marked as a moment that is forever embedded in his mind.
5 JOKER FORCES BATMAN TO MAKE A CHOICE
Taking a page again from "Death of the Family", the climax of the story involves Joker reciting a monologue about the dichotomy between him and the Dark Knight. However, the whole Bat-family is restrained, and if Batman were to free himself with his sheer might, he would risk scratching the flint stones underneath his chair and igniting the gasoline that's been sprayed all over his family.
Joker lights a match and tells Batman that if he doesn't make the choice to burn them, then he will. Luckily, Batman knows a way out of this, and saves his true loved ones, but that moment had readers believing otherwise.
4 BARBARA'S DEPRESSION
After the events of The Killing Joke, Barbara is confined to a wheelchair, due to the paralyzing injuries she suffered by Joker's hand. This would traumatize anyone and give them a bad case of PTSD, but Barb is a special case due to her position as Batgirl.
During her therapy sessions, she would explain her nightmares she has about the Joker, where she regained the use of her legs and took him out, stating that she would sometimes wake up crying in cold sweats either in fear, or simply because she was only dreaming about those fantasies. Fortunately, she regains her health and dons the cowl of Batgirl once again in the New 52 era, but the memories still stand.
3 TALIA DISOWNS DAMIAN
Talia al Ghul has a very on-and-off relationship with Batman, despite her not being as close as to him as Catwoman is. However, she does harbor love for her son, Damian Wayne, even though she clones him on a regular basis. At the time of Dick Grayson taking the mantle of Batman during Bruce Wayne's absence, Damian confronts Talia and makes the discovery that he has a clone brother.
Talia finally understands that Damian made the choice to become Robin, and that he fully commits himself to it. The perfectionist in her sees this as a flaw in his design and disowns her own son, making him an enemy of the house of al Ghul -- something Damian is proud of.
2 BATGIRL WAS FORCED TO MARRY THE JOKER
Shortly before the final events of the "Death of the Family" story arc, Barbara Gordon's mother had been taken by the Joker, with events playing out similarly like they did in The Killing Joke. Barbara dons her work clothes, and then proceeds to track down the Joker to a bowling/skating alley he is secluded in, with her mother held there.
As it turns out, Joker severed her mother's finger with her wedding ring on it, and he uses it to unexpectedly propose to Barb. Batgirl heads to the local church where a priest is also being held, along with his congregation. All this has happened to Barbara again because Joker needed a few laughs.
1 JOKER FINALLY GETS NIGHTWING
As stated before on this list, Joker despises the first Robin the most, largely due to the fact that he never got the chance to scar him for life. Unfortunately for Grayson, Joker finally got his wish, as Joker struck down some of Dick's personal friends.
Not only that, but he also dug up former Haley's circus members, and strung them about for Nightwing to see. All of this torment climaxes with a number of Dick's closest loved ones fighting him to the bitter end as they are filled with Joker's mind control toxin.