Chris Pine has described his 2014 film Jack Ryan: Shadow Recruit as one of his "deep regrets", admitting that the production did not live up to its potential. The film saw Pine become the fourth actor to play Tom Clancy's CIA analyst Jack Ryan, following Alec Baldwin, Harrison Ford and Ben Affleck, but unlike its predecessors it was an original story rather than a novel adaptation. Despite a cast including Keira Knightley, Kevin Costner and director Kenneth Branagh, the film was intended to boost Pine's career but instead received mixed reviews and a lukewarm box office return.

Released shortly after Clancy's death, Shadow Recruit grossed $135 million against a $60 million budget and was criticised as a derivative spy thriller, with Knightley's performance drawing particular scorn even as Pine's was praised. CinemaScore data showed only 15% of its audience was under 25, with the average viewer aged over 50, reflecting its failure to attract younger cinemagoers. The Jack Ryan franchise later resurfaced via John Krasinski's Amazon Prime television series and subsequent film Jack Ryan: Ghost War, though its critical reception fell short of the revival Pine had hoped for.