Thomas Jane was originally attached for the lead role, but he turned it down, stating that he thought the script was going in the wrong direction. He felt it was too "comic book," whereas he wanted a more gritty, realistic approach.

"Sons of Anarchy (2008)" creator Kurt Sutter wrote an R-rated draft that, according to him, took "the Punisher character out of the comic books" and put him into a real-world drama set in the streets of New York. At the very last minute, however, the studio decided to revert to Nick Santora's comic-book-style script with the intention of creating a sequel from that. Disgusted with the actions by the studio, Sutter refused a story credit and demanded that his name be omitted from the final credits.

According to director Lexi Alexander during a recording of the "How Did This Get Made" podcast, the studio brought in Freddie Prinze Jr. to audition for the role of Jigsaw. She was surprisingly impressed by his audition, however was denied the right of casting him by Lionsgate.

Lexi Alexander initially passed on directing the film but later changed her mind after reading some of the Punisher comics and getting an assurance from Lionsgate that she could make the film as brutal as she liked, and that she could cast another actor as Frank Castle.

Originally, this film was going to be a direct sequel to The Punisher (2004), with Thomas Jane returning in the role of Frank Castle. It was to be set five years after the 2004 film and would see Frank Castle arrive in New York and taking on Jigsaw, who is plotting to take control of the criminal underworld. However, when Jane declined, the film was rebooted and the script was rewritten and Ray Stevenson was cast as Frank Castle. However, Jane did reprise the role in the 2012 short film The Punisher: Dirty Laundry (2012).