Appearing in 1st story
- Iron Man (Tony Stark) (Main story and flashback)
- Avengers (Mentioned)
- Mrs. Gillespie (Cassandra Gillespie's mother) (Mentioned)
- Giorgio Gillespie (Mentioned)
- Hydra (Mentioned)
- Maria Stark (Mentioned)
- Sofia Central Police Department (Mentioned)
- S.H.I.E.L.D. (Mentioned)
- Tony's biological father (Mentioned)
Races and Species:
- Humans (Main story and flashback)
- Earth (Main story and flashback)
- United States of America (Only in flashback)
- United Kingdom (Only in flashback)
- Gillespie Compound (First appearance)
- New Zealand (Only in flashback)
- Auckland (Only in flashback)
- Hell (Mentioned)
- S.H.I.E.L.D. Helicarrier (Mentioned)
Synopsis for 1st story
Twenty years earlier, in the Stark Mansion, Howard Stark wakes up and talks to Tony in the mansion's garden. Howard warns Tony of the danger the Gillespies pose, being ill-intentioned weapons dealers. Howard reviews the events that transpired on the night of Hydra's attack, and concludes that it was a set up for Tony to get closer to Cassandra. Tony remains skeptical.
Back to the present, the Mandroids take Stark's armor from him and leave, fearing to attract the attention of local authorities. One of the Mandroids even apologizes to Tony, claiming to be a big fan of his, before leaving.
Two decades into the past, Howard wakes up in his mansion to be informed by his assistant that Tony has escaped. In Cambridge, Cassandra is accompanied by several bodyguards to her apartment. When she enters the bathroom, she's surprised by Tony himself, who had traveled all the way to England off the grid, and had broken into Cassandra's apartment after investigating her schedule and figuring out the moment to enter, using a prototype cloaking device to remain hidden from the guards. Cassandra is comforted by Tony's presence, and both decide to run away together.
In the present, Cassandra's Mandroid army brings Iron Man's armor to her in Bucharest. She fears that the armor could be emanating a signal for tracking, but his men had found no energy source or frequency coming from the suit. Regardless of the suit's apparent harmlessness, she orders them to take the armor to a warehouse up North. Cassandra enters her compound, and when she gets into the bathroom, she's surprised by Tony. Even if his armor was emitting no signal, he still had other means to use it for tracking. Cassandra attempts to point her gun at Tony's temple, but when she draws near the weapon, she discovers Tony is wearing another armor in self-camouflage mode. Tony demands Cassandra lower the gun and talk.
In the past once again, Tony and Cassandra have been navigating New Zealand's waters on a sailboat. When Tony reveals to Cassandra what his father thought of her and rejoices that he was supposedly wrong about Cassandra's intentions, she breaks down and admits that their relationship had begun as an attempt of her mother to learn of Howard; however, Cassandra admits to having developed real feelings towards Tony.
In the present, Tony tries to get Cassandra to talk about the whereabouts of his biological father, after his investigation had led him to her.
• As Tony’s troubled past comes to the present new villains and allies are introduced. And Tony inches ever closer to finding out the identity of his birth parents.
• A Civil War II prologue story.
• From the creative team that brought you Daredevil’s darkest chapter.