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'Avast ye landlubbers! Thar be Spoilers off the port bow!'
Jackaroe[]
Mary "Jacky" Faber
- Action Girl
- Catch Phrase: "I am so very hard on my friends" and "Men, i swear."
- And "I am not shy in that regard." And "It's just that i wasn't raised up proper." Jacky has a lot of these.
- "I am promised to another," and its replacement, "I have sworn to live single all of my days," from when she temporarily breaks up with Jaimy in Under The Jolly Roger.
- Cowardly Lion
- Embarrassing Nickname "Puss-in-Boots", "Princess Pretty Bottom"...
- Her Indian name means "She Who Dances Like Crazy Rabbit" but Jacky doesn't mind because she's been called worse.
- Even the Girls Want Her: Mam'selle Claudelle de Bourbon and Cheng Shih
- Genki Girl
- Good Angel, Bad Angel Starting in Rapture of the Deep "Little Mary" starts showing up.... "Jaaaaackyyyyy... TREASURE, JACKY!"
- High Octane Nightmare Fuel Appropriately, in her nightmares, including Pirates with rotting heads, and being chained to an anchor with other girls and thrown overboard. She rarely can sleep alone.
- Large Ham
- Master of Disguise
- Mike Nelson, Destroyer of Worlds Beginning in Curse of the Blue Tattoo when she accidentally burns down Boston, Mass..
- Privateer: At least, she thought she was.
- Shipper on Deck: Jacky is instrumental in getting some of her friends together as couples. Especially evident in the case of Amy and Ezra, when Amy insists she "isn't ready for that sort of thing yet."
- The Social Expert: She learned the skills she needed to become one, mostly because she had to for the sake of survival.
- Street Performer: Often turns to this as an emergency money-making scheme.
- Sweet Polly Oliver Of course. Almost once per book she'll dress in men's clothing.
- Tomboy and Girly Girl: Jacky is the tomboy, with Amy as girly girl.
- Wholesome Crossdresser: She often wears men's 'rig' even when she isn't playing Sweet Polly Oliver. Usually it's whenever skirts aren't particularly practical but sometimes she just wants to put on trousers.
The Lawson Peabody School For Young Girls[]
Amy Trevelyne
- Catch Phrase: "Oh, Jacky, no!" and "I'm not ready for that sort of thing yet."
- Friend to All Living Things At least, "All Living Things" seem to think she's this. Hilariously used in In The Belly of the Bloodhound with some seals "Oh Amy, 'E's looking at you in a Husbandly Way, 'e is!".
- I Should Write a Book About This: Amy publishes Jacky's adventures in-universe.
- Tomboy and Girly Girl: With Jacky.
Clarissa Worthington Howe (Of the Virginia Howes)
- Foe Yay / Les Yay: With Jacky.
- Rich Bitch
Jacky's Harem of Boyfriends[]
James Emerson Fletcher
- Berserk Button Do NOT talk ill of Jacky in front of him. It won't end well.
- Beware the Nice Ones The villains of the series often mistake Jaimy's being a gentleman for being weak.
- Bishonen A number of girls remark on how beautiful/pretty he is.
- Even the Guys Want Him: Clementine's father and a few others.
- First Guy Wins
- Heroic BSOD: In The Mark Of The Golden Dragon, after Jacky gets washed overboard during a typhoon. Leads to him becoming a highwayman to kill the people he sees as responsible.
- Sanity Slippage: Starting with his head trauma in My Bonny Light Horseman.
- Skunk Stripe In My Bonny Light Horseman, a scar across his scalp leaves him with this.
- Sweet on Polly Oliver: Was he ever happy to find out Jacky was a girl.
- Took a Level in Badass In Mississippi Jack.
Joseph Jared
Randall Trevelyne
Jean-Paul de Valdon
Flaco Jimenez
- Badass Spaniard
- Latin Lover: At least, one of the hopefuls.
- Loveable Rogue
- Pirate
Captain Richard Lord Allen
- Chivalrous Pervert
- First-Name Basis Insists (despite his birth) that Jaimy regard him "Richard" or "Dick".
- They Call Me Mister Tibbs Insists that Flashby call him "Lord Allen" in a clear showing of disdain.
Arguably Cheng Shih
- Chinese People: No, she doesn't count as an Anime Chinese Girl.
- Historical Domain Character
- I Want My Beloved to Be Happy: She lets Jacky go with Jaimy, even though Jacky promised to stay with her forever.
- Les Yay
- Pirate Girl
Jacky's Crews[]
Mr. John Higgins
- Ambiguously Gay
- Battle Butler Constantly dual-wielding percussion cap pistols.
- The Jeeves Often providing moral guidance to his wayward Jacky while washing her hair.
- Servile Snarker: Sometimes.
Liam Delaney
- Papa Wolf
- Team Dad: He's Jacky's "sea dad" in the first book, acting as a mentor to her on the ship.
Máiread Delaney
- Fiery Redhead
- I Always Wanted to Say That: "Stand and Deliver!"
Clementine Amaryllis Jukes
- Moe Big Blue Eyes? Check. Adorable freckles? Check? Lawson-Peabody Standard-Issue Meido Outfit? Double-Check.
- First Girl Wins Sorry, Clemmie. Jacky got there first
Jemimah Moses
Enoch Lightner
Ravi
- Street Urchin
- Survival Mantra: "Happy puppy, happy puppy, happy puppy..."
The Rooster Charlie Gang[]
"Rooster" Charlie Brewster
Polly Von
- Blue Eyes
- Cry Cute: Her whole schtick.
- Hair of Gold
Hugh the Grand
- Huge Guy, Tiny Girl Hughie & "Little Mary" were a team, with Mary Faber riding on his shoulders
Joannie Nichols
[]
Mr. Peel
Carr and Boyd
Henry Flashby
- Cold-Blooded Torture: Holds his cigar to Jacky's leg after making her think he was going to blind her with it.
Alexander Bliffil
Other Adversaries[]
Mike Fink
- Badass Boast Many of the Tall Tales surrounding Mike Fink are his own invention, it seems.
- Bar Brawl Immediately upon setting foot in Pittsburgh.
- Catch Phrase: "I'm a ring-tailed roarer!"
- Large Ham
- Public Domain Character
- Squash Match Between him and Jaimy.
Outright Villains[]
Captain Scrogg
Ruger
- Loony Fan He's read the Bloody Jack novels, and identifies Jacky by her tattoo.
- Moral Event Horizon viciously assaults the pregnant Mairead
- Stalker with a Crush