The Highwayman

The Highwayman is a hidden side job found in the game world by V in.

Walkthrough
To begin this side job, first, head over to Rancho Coronado East and travel up the street to the Guns'O'Rama gun shop. Around the back you'll find an accessible garage with a decal of a ghost horse to the left of it.

Once inside, V and Johnny will comment on the scrapped Brennan found inside. To officially start the side job, access the terminal on the opposite side of the garage. After reading the data stored, exit the terminal and V will pick up the photo of James Ito and Josie Alcazar resting next to it. This prompts V and Johnny to look for James to find out more about their situation.

To find James, travel to Japantown West and head south to the nearby public space with a 24/7 convenience stand. James is sitting on the same bench in the photo, in front of the 24/7 stand. Talking to him will begin your investigation into what happened to Josie.

To find out what happened to Josie, head to Metro: Glen North on the map. From the metro, travel east on the sidewalk with your scanner active until your near a drop point. Your scanner will pick up a dried blood splatter on the ground. Immediately to your right is an alleyway; and behind a dumpster, Josie's body.

There will be a shard labelled "Bad news" which details Josie's cause of death as well as information on the location of the bike she stole from a Tyger Claw boss. After having an exchange with Johnny, it's time to return to James in Japantown and confront him about what you've discovered. What happens to James after confronting him is up to you. After the confrontation, you will need to find the Tyger Claw boss's bike in order to complete the job.

The shard found on Josie's body mentions it being stowed on Maelstrom turf by All Foods. This will send you to the All Foods Plant in the Northside of Watson. Across street from the travel point, you'll see the "ghost horse" that Josie also mentioned in the shard. The bike is in the nearby garage. Punch in the date that James and Josie met (0214) into the keypad next to the garage and it will open.

Journal Entry

 * There's a still of some young guy in the garage - the heartbreaker type. Emails on the computer are from a certain James - don't have to be a genius to connect the dots. Might be worth looking for our Romeo - especially in Japantown. Got a feeling the still was snapped there. Wouldn't surprise me - kids go on dates there all the time. Shit... it always starts off so cute, doesn't it? Rarely ever ends that way.
 * Josie hid the Tyger boss's bike somewhere in the city, near the All Foods factory in Maelstrom turf. Said to look for a "ghost horse." All right then... Think of it like a scavenger hunt, though not the kind fixers in Night City usually pay you for.
 * Josie... Pretty name. Cute girl. Ugly end. This Tyger from the still... better have a word with him, V. Can't let slide what he did to this poor girl.
 * Another mystery, another missing person in Night City. Used to be the cops would put out a search for people like her. Today, her fate's in your hands.

Objectives

 * Find James.
 * Find out what happened to Josie.
 * Find James and confront him.
 * Find the stolen Tyger Claw bike.

Trivia

 * The Highwayman is a poem by Alfred Noyes published in 1906, with a story arc closely tied to the themes of the quest. The last two stanzas include imagery of a ghostly horse and rider.