Charlie Cox and Deborah Ann Woll discussed Frank Castle's comment to Spider-Man about friendship in Spider-Man: Brand New Day, and their response was playful but pointed. Jon Bernthal's Punisher made his big-screen debut in Brand New Day, showcasing his unexpected friendship with Tom Holland's Spider-Man. One of the film's most talked-about moments comes near the end, when a wounded Peter Parker wakes up in the hospital with Frank at his bedside. After a tense alliance throughout the movie, Punisher looks at the younger hero and quietly admits, "Nice kid. Never had a friend like that." That simple line landed with surprising emotional weight, signaling a rare soft side from the usually stoic vigilante. For many fans, however, the remark also raised eyebrows, considering Frank Castle's long history with Matt Murdock and Karen Page.
During a special Q&A at MCM Comic-Con Birmingham 2026, Charlie Cox and Deborah Ann Woll were asked by TikTok user CinemaKaiNation about the memorable Spider-Man: Brand New Day moment in which Frank told Peter he had "never had a friend like that."
Deborah jumped in first, declaring she was more offended on Karen Page's behalf than Matt's:
"Actually, I'm more offended by that for Karen, rather than Matt. Jesus Christ, Frank. Goddamnit. How many times have we saved each other's lives?"
Charlie quickly agreed, noting that while Matt and Frank share a deep mutual understanding and respect, they would never really call each other friends or mates.
"Yeah, I think [Deborah] is right. Matt and Frank, I don't know that they'd call each other [friends]. I think there's a mutual understanding and respect, but they're now mates."
When asked to define the relationship status between Daredevil and the Punisher, Cox teased, "It's complicated."
In the MCU's street-level corner, Karen Page and Frank Castle shared one of the most unexpected and emotionally charged friendships.
While most of the world saw Frank as a ruthless killer, Karen recognized him as a traumatized man driven by revenge due to the murder of his family. The pair formed a deep bond that carried over into other projects, most notably The Punisher (Seasons 1 and 2) and Daredevil: Born Again (Season 1).
In 2026's The Punisher: One Last Kill, a hallucination of Karen appeared to Frank at a low point, serving as both a source of comfort and a parallel to Frank's late wife.
Karen is one of the few people Frank trusts and softens around, which explains why Deborah Ann Woll was quick to be offended on Karen's behalf when Frank told Spider-Man he'd "never had a friend like that."
As for Matt, he and Frank had one of the most intense yet strangely respectful relationships in the MCU. The complicated dynamic began in Daredevil Season 2, then they set aside their differences and teamed up again in Daredevil: Born Again against Mayor Wilson Fisk's Anti-Vigilante Task Force. At this stage of their lives, Frank and Matt are still ideological opposites who keep orbiting each other.
Punisher’s Return in Spider-Man: Brand New Day Sets Up a Reunion With Karen Page & Matt Murdock
The Punisher's presence in Spider-Man: Brand New Day humanized Frank Castle in more ways than one and raised questions about his future and how he was forever changed by his experience with Spider-Man.
With Matt currently imprisoned following the events of Daredevil: Born Again Season 2 and Karen Page still navigating the fallout from Fisk's regime's collapse, Frank's newfound softness toward Peter feels like both a deliberate parallel and a setup.
Brand New Day positioned Frank as someone capable of genuine attachment again, laying the groundwork for when he inevitably crosses paths once more with the two people who knew him best.
Whether that reunion happens in Daredevil: Born Again Season 3 or a future street-level crossover, Spider-Man: Brand New Day has already planted the seeds. Frank Castle, with his renewed bravado and confidence, is no longer operating in complete isolation. This time, the emotional door is open for Frank. After years of strained alliances and missed chances with Karen and Matt, the responsibility to reconnect may finally rest with him, if he chooses to walk through it.
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