Nightwing isn’t just Batman’s former sidekick—he’s a hero who carved his own legend through sheer determination, agility, and heart. Dick Grayson’s transformation from Robin into Nightwing marked a turning point not only in his life but in the entire Bat-Family’s dynamic. Since then, he’s taken on global spy rings, superpowered criminals, and conspiracies that threatened entire cities. Unlike Bruce, Dick leads with empathy, connecting with people in ways Batman rarely does. But that doesn’t mean he avoids danger—in fact, some of Nightwing’s missions have been so perilous, only someone with his unique blend of charisma and combat prowess could survive.
#10: Infiltrating the Court of Owls (Nightwing Vol. 3, “Night of the Owls,” #8–#9)
One of the most harrowing arcs of Nightwing’s career begins with the revelation that the Court of Owls—a secret society that manipulates Gotham from the shadows—has ties to Dick Grayson’s own bloodline. The mission becomes personal when Dick learns he was destined to become a “Talon,” one of the Court’s elite undead assassins, had Bruce Wayne not adopted him after his parents’ death.
Dick doesn’t just fight the Court—he has to infiltrate them, earning their trust while dismantling their plans from within. This puts him face-to-face with an army of Talons, undead killers trained in ancient martial arts and enhanced by science. At one point, Nightwing is nearly killed by his own great-grandfather, William Cobb, one of the Court’s deadliest operatives. The emotional trauma of learning that his family was part of Gotham’s darkest cabal—and that his entire destiny was manipulated—is nearly as crushing as the physical threats he faces.
Despite the overwhelming odds, Dick pushes through, exposing the Court’s influence in Gotham and helping Batman purge them from power. But the scars—both literal and psychological—run deep. This mission didn’t just test Nightwing’s skills—it forced him to question everything about his identity, past, and future.
#9: Undercover in Spyral (Grayson #1–20)
After the world believes Dick Grayson has died during the events of Forever Evil, Batman sends him undercover into the espionage organization Spyral. This mission isn’t just dangerous—it completely shatters Dick’s usual approach to heroism. Forced to operate without his costume, code name, or support network, Dick becomes Agent 37, infiltrating a group that spies on metahumans and collects their secrets.
Working for Spyral tests Dick’s moral compass. He’s ordered to seduce, manipulate, and even kill—all actions that conflict with his core beliefs. He walks a razor-thin line, trying to protect innocents while feeding Batman intel from the inside. The mental toll is immense, especially when he learns Spyral is using facial-obscuring technology to erase the identities of heroes and enemies alike.
Things take an even darker turn when he discovers the agency’s experiments on children and brainwashing tactics. His cover nearly blows multiple times, including during clashes with Midnighter and other spies who suspect his true motives. Every day as Agent 37 puts Dick in mortal danger, but he perseveres, dismantling Spyral from within while maintaining his soul—a feat few could achieve.
#8: Surviving Blockbuster’s War on Blüdhaven (Nightwing Vol. 4, #78–95)
When Dick inherits Alfred’s fortune and decides to revitalize Blüdhaven, he paints a massive target on his back. Roland Desmond, aka Blockbuster, returns with a vengeance, declaring war on Nightwing and using everything from assassins to political manipulation to break him. The mission? Save Blüdhaven’s soul from a crime syndicate embedded in every level of its government.
Nightwing faces physical attacks from some of DC’s most dangerous mercenaries—Heartless, Brutale, and even KGBeast. But the real challenge lies in surviving the constant mental and emotional strain. Blockbuster turns the city against him, forces him to question whether he’s making a difference, and even uses children as pawns in his schemes.
Despite these threats, Nightwing refuses to back down. He builds shelters, funds education, and fights corruption with both fists and financial power. The turning point comes when Blockbuster learns Nightwing’s secret identity and puts his loved ones in immediate danger. In the end, Dick survives not by brute force, but through compassion and community—a rare combination in the superhero world. This mission proved Nightwing wasn’t just the protector of Blüdhaven—he was its beating heart.
#7: The Raptor Conspiracy (Nightwing Vol. 4, #1–15)
One of Nightwing’s most disturbing missions involves his reluctant alliance with Raptor, a brutal antihero who claims to share Dick’s values but uses horrifying methods to enforce them. Dick infiltrates the Parliament of Owls—a global offshoot of the Court of Owls—and teams up with Raptor to dismantle the organization from the inside.
At first, Raptor appears to be a valuable ally—if unpredictable. But as the mission progresses, Dick realizes that Raptor has a deeply personal grudge against Bruce Wayne and is manipulating Dick to fulfill his vendetta. Raptor reveals that he knew Dick’s mother and that her death could have been prevented—had Bruce acted differently. This emotional bombshell shakes Dick to his core, making him question his loyalty to Batman and the moral high ground he’s fought so hard to maintain.
The mission becomes a psychological gauntlet, with Raptor pushing Dick toward a darker path. Their final battle isn’t just physical—it’s philosophical. Dick triumphs, but not without scars. He walks away with a deeper understanding of what separates him from the criminals he fights: not just his actions, but his refusal to become the monster.
#6: Leading the Teen Titans into War (The Judas Contract, Tales of the Teen Titans #42–44, Annual #3)
When Nightwing steps into leadership of the Teen Titans, he doesn’t inherit a peaceful team of sidekicks—he inherits a warzone. The Judas Contract is one of the most iconic and dangerous missions of his early career, putting him up against not just Deathstroke, but a traitor within his own ranks: Terra.
As the Titans face mounting threats from the mysterious H.I.V.E. organization and the unrelenting assassin Deathstroke, Dick sheds his Robin identity and becomes Nightwing for the first time. But this moment of evolution is quickly marred by betrayal when Terra—whom the team had trusted—reveals she’s been working with Deathstroke all along. The team is captured, and Dick is forced to operate completely alone, on the run and stripped of his usual resources.
What makes this mission so dangerous isn’t just the overwhelming enemy force or the betrayals—it’s the emotional trauma. Terra’s betrayal shakes the team to its core, especially Beast Boy. Deathstroke nearly kills Dick multiple times, and for once, the Titans are truly unprepared. Nightwing’s brilliant strategy, relentless courage, and capacity to rally his friends save the day, but not without permanent scars.
This mission cemented Nightwing as more than Batman’s former partner—it proved he could lead, plan, and win on his own terms. It was a trial by fire that redefined who Dick Grayson was—and who he could become.
#5: Saving Gotham from The Joker (Joker: Last Laugh, Crossover Event)
In the sprawling crossover Joker: Last Laugh, the Clown Prince of Crime discovers he’s dying from a brain tumor and decides to go out with a bang—by infecting dozens of villains with a version of his Joker toxin. This causes mass hysteria across the DC Universe as heroes scramble to contain a wave of murderous, laughing maniacs. Nightwing is at the epicenter of this crisis, tasked with protecting Gotham while Batman is away.
The situation quickly spirals out of control. Nightwing battles Jokerized versions of villains, innocent citizens, and even other heroes. One of the most intense confrontations occurs when Dick must face off against a Jokerized version of Captain Marvel Jr., whose powers make him nearly unstoppable. The violence is relentless, and the psychological warfare takes its toll.
But the most dangerous moment comes when the Joker manipulates Nightwing into believing he’s killed someone—forcing Dick to question whether he’s fallen into the same trap that once haunted Jason Todd’s legacy. As chaos spreads and the lines blur, Nightwing is faced with the terrifying possibility that he might have to kill the Joker to end it all.
He doesn’t. But the mission leaves him shaken, forever marked by the Joker’s games. It was a battle for Gotham’s soul—and for Nightwing’s.
#4: Fighting in the Dark Multiverse (Dark Nights: Death Metal, Event Crossover)
In the Death Metal event, the multiverse collapses into madness, and the Earth becomes a twisted hellscape ruled by The Batman Who Laughs. Nightwing is thrust into a resistance effort alongside Wonder Woman, Superman, and others to restore the multiverse—and it’s by far one of the most surreal and dangerous missions he’s ever taken on.
Stripped of familiar landmarks, facing nightmare versions of his allies and enemies, Dick Grayson steps into a leadership role among the survivors. He battles monsters created from the darkest corners of the multiverse, navigates terrain where reality itself is unstable, and reunites with alternate versions of himself who didn’t survive their own worlds.
One of the most brutal moments involves his confrontation with the Robin King—an evil child version of Bruce Wayne who gleefully slaughters heroes. Nightwing goes toe-to-toe with him, holding his own while the multiverse crumbles around them. There are no safe zones, no rules, and no second chances.
Through it all, Nightwing proves why he’s a pillar of the DC Universe. Even amid cosmic destruction, he holds the line—not because of powers, but because of belief. Belief in people, in legacy, and in rebuilding. It’s one of his most epic and soul-defining arcs.
#3: Surviving Forever Evil (Forever Evil, Event Crossover)
During Forever Evil, the Crime Syndicate—evil versions of the Justice League from Earth-3—invade and conquer Earth. Most of the heroes are presumed dead, and Nightwing is captured, unmasked on live television, and tortured by Owlman and Superwoman. His identity as Dick Grayson is made public, endangering everyone he’s ever loved.
The Syndicate then places Dick in a death trap—a device wired to his heartbeat. If he dies, a bomb will go off, killing thousands. Lex Luthor is forced to “kill” him temporarily to disarm it. It’s a harrowing, humiliating experience for Dick, who has never been so vulnerable or so publicly compromised.
But what truly makes this mission dangerous is what comes after. With his identity blown and the world believing he’s dead, Dick is forced to go underground, setting up the events of his infiltration into Spyral. The mission tests his loyalty, his patience, and his sense of purpose. For a time, Nightwing ceases to exist. Dick becomes something else—something even more isolated and dangerous.
The trauma of Forever Evil reshapes Dick Grayson’s path, turning a street-level hero into a ghost in the machine. It wasn’t just a physical test—it was an existential one.
#2: Operation Sanctuary (Nightwing Vol. 4 #50–56, “The Ric Grayson Arc”)
After being shot in the head by the KGBeast, Dick Grayson suffers amnesia and loses all connection to his past life. This isn’t a classic mission—it’s a survival story. With no memory of being Nightwing or Robin, Dick becomes “Ric Grayson,” a taxi driver in Blüdhaven who wants nothing to do with heroism. But fate doesn’t care.
As Ric, he’s drawn into a web of crime, police corruption, and supervillain conspiracies. He battles villains like Talon and The Judge without the benefit of training, memory, or resources. Every fight is life-or-death. Every decision is a coin flip between instinct and confusion.
Eventually, Ric slowly begins to remember his past and chooses to become Nightwing again—not because of legacy, but because of choice. This makes his journey one of the most emotionally perilous missions of all. He literally rebuilds himself from scratch, deciding who he wants to be without the shadow of Bruce Wayne guiding him.
Operation Sanctuary is Nightwing’s resurrection arc—a mission of rediscovery that proved no matter who Dick Grayson is, he’s always a hero.
#1: Defending Earth from Brother Eye (Futures End & Earth 2: Futures End)
In a dystopian future ruled by the sentient AI Brother Eye, Dick Grayson becomes one of Earth’s last surviving heroes. With most of humanity either dead or assimilated, Dick is one of the few capable of navigating enemy territory and resisting cybernetic assimilation. He’s no longer just a vigilante—he’s the rebellion’s final hope.
This version of Dick is grizzled, hardened, and utterly focused. He leads rescue missions, hacks alien technology, and outwits Brother Eye’s adaptive drones. His closest allies are gone. Batman is long dead. And every mission could be his last. The pressure is constant, the enemies relentless, and the stakes cosmic.
Eventually, he’s captured and partially assimilated—but even then, his spirit holds firm. He turns Brother Eye’s programming against itself, leading to a last-ditch effort that reboots the timeline and gives Earth another chance.
It’s the most dangerous mission he’s ever taken—not just because of the physical threats, but because the fate of everything depends on him. In a future without hope, Dick Grayson proves he is hope. And that makes this his most powerful—and perilous—mission ever.
Nightwing has faced more than just street-level crime—he’s tackled secret societies, survived brainwashing, led global resistance movements, and even died and come back stronger. These missions reveal the full spectrum of what makes Dick Grayson not just a former sidekick, but one of the DC Universe’s most essential heroes. Whether he’s wearing the domino mask or hiding in the shadows as a spy, Nightwing stands for courage, resilience, and heart. He doesn’t just survive these deadly missions—he grows stronger with every step, proving that sometimes, the brightest hero comes from the darkest shadows.
