''''Avast ye landlubbers! Thar be Spoilers off the port bow!''''

!Jackaroe

'''Mary "Jacky" Faber'''

Our wayward heroine, who starts off as one of the pluckiest ship's boys on the bounding main despite being a girl. But she's bound for bigger things, our Jackie... if she doesn't manage to get herself hanged in the meantime.

* ActionGirl: Sailor, spy, soldier...Jacky rises to just about every occasion.
* AFatherToHisMen: Very much Jacky's leadership style. Even when she's confined to the brig (which is fairly often) she thinks of her guards as "My Marines" and treats them as such. Foster mother to baby Jesse and later to Ravi.
* BestServedCold: But only in the form of RestrainedRevenge, like forcing Davy to learn how to swim in the seventh book by tying him to a rope and throwing him overboard in revenge for slights from the first book. Or taking revenge on the surviving crewmen of the Bloodhound by winning their loyalty four books after she'd marooned them at sea.
* CatchPhrase: "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''.
** "I'm a good girl... mostly."
** "I never was very brave." (Usually employed after Jacky has done nothing but feats of derring-do.)
** "I always feel better with a plan." (Usually employed after Jacky has come up with a seat-of-the-pants, harebrained scheme that's just crazy enough to work.)
* CowardlyLion: And isn't afraid to admit it, at least to herself. Jaimy recognizes it too, though, and mentions it in one of his reports.
* DefeatByModesty: Jackie is completely immune to this trope (on account of being "not shy in that regard" because she wasn't "raised up proper") as more than one would-be rapist has discovered to his cost.
* DoubleStandard: Constantly crashing headlong into it when she isn't playing it to her advantage.
* EmbarrassingNickname "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.
* EvenTheGirlsWantHer: Mam'selle Claudelle de Bourbon [[spoiler:and Cheng Shih]]
* FamedInStory: The common seamen of the Royal Navy call her "Puss-in-Boots", consider her a good luck charm, and practically worship the deck she walks on. [[spoiler: Her fame becomes even more widespread once Amy starts writing up her adventures...which is kind of a problem, when you're wanted for piracy.]]
* GenkiGirl
* GoodAngelBadAngel: Starting in ''Rapture of the Deep'' "Little Mary" starts showing up.... "Jaaaaackyyyyy... TREASURE, JACKY!"
* HeroWithBadPublicity: Jackie once got a pirate to talk by pretending to torture his shipmate (it was all a scam, of course.) Ends up [[HoistByHisOwnPetard hoist by her own petard]] when Flashby uses the incident to justify torturing her for real.
* ImprobableAge: From ship's boy to midshipman to fine lady to pirate to soldier to spy to convict to merchant all by the age of 18.
* LargeHam: Jacky *knows* she's a large ham and often plays up her caterwauling and/or feminine modesty in dangerous situations, so that people will back off just to shut her up.
* MasterOfDisguise: Passing herself off as a boy in the first book seems to have uncovered a talent for disguise. She does it once per book, at least.
* MikeNelsonDestroyerOfWorlds: Beginning in ''Curse of the Blue Tattoo'' [[spoiler: when she accidentally [[KillItWithFire burns down]] half of Boston, Massachusetts]].
* {{Privateer}}: At least, she thought she was.
* PuppyDogEyes: Jacky calls this technique "the big eyes" and is quite strategic in its employment.
* ScarsAreForever: Jacky has one on her eyebrow, one on the outer edge of her opposite eye, and a faint constellation of tiny blue powder burns around her right eye that she hides with makeup. She got the burns sighting a cannon at the battle of Trafalgar.
* SheCleansUpNicely: Jackie has a noticeable fondness for pretty clothes whenever she's not being a WholesomeCrossdresser or a SweetPollyOliver. While even she'll tell you she's not exactly beautiful, people find her blonde hair and sharp features appealing.
* ShipperOnDeck: Jacky is instrumental in getting some of her friends together as couples. Especially evident in the case of Amy and Ezra, when Amy insists [[CatchPhrase she "isn't ready for that sort of thing yet."]]
* TheSocialExpert: She learned the skills she needed to become one, mostly because she had to for the sake of survival.
* StreetPerformer: Often turns to this as an emergency money-making scheme.
* SweetPollyOliver: Of course. Almost once per book she'll dress in men's clothing.
* TomboyAndGirlyGirl: Jacky is the tomboy, with Amy as girly girl.
* WholesomeCrossdresser: She often wears men's 'rig' even when she isn't playing SweetPollyOliver. Usually it's whenever skirts aren't particularly practical (like at sea) but sometimes she just wants to put on trousers.
* VirginPower: Despite all of her escapades, Jackie has so far managed to avoid being deflowered, which provides her with a great deal of moral suasion and the ultimate defense when adversaries accuse her of immorality.

!The Lawson Peabody School For Young Girls
'''Mistress Pimm'''

The stern headmistress of the Lawson Peabody School For Young Girls.
* IronLady: The woman’s backbone might as well be pure steel.
* MamaBear: You DON’T mess with the Lawson Peabody girls. The kidnapping staged at the beginning of ''In The Belly of the Bloodhound'' relied on Mistress Pimm being too sick to notice, and it DID NOT keep her down long.
* ReasonableAuthorityFigure: She is STRICT, but NOT CRUEL. She looks after her students ferociously.
'''Amy Trevelyne'''
* CatchPhrase: "Oh, Jacky, no!" and "I'm not ready for that sort of thing yet."
* FriendToAllLivingThings At least, [[LickedByTheDog "All Living Things"]] seem to think she's this. Hilariously used in ''In The Belly of the Bloodhound'' with some seals [[spoiler: "Oh Amy, [[TheFairFolk 'E's]] looking at you in a [[ShapeShiftingLover Husbandly Way]], 'e is!"]].
* IShouldWriteABookAboutThis: Amy publishes Jacky's adventures in-universe.
* TomboyAndGirlyGirl: With Jacky.

'''Clarissa Worthington Howe (Of the Virginia Howes)'''

Jackie's nemesis at Lawson Peabody, she'll do almost anything to get a rise out of Jackie, or better yet, get her expelled.
* GreenEyedMonster: Her enmity turns out to be half snobbery, half jealousy; she envies Jackie's independence and freedom.
* RichBitch: And not afraid to bring it up, along with her prestigious family background.

!Jacky's Harem of Boyfriends

'''James Emerson Fletcher'''
%% Doesn't explain what the reaction is. * BerserkButton Do '''NOT''' talk ill of Jacky in front of him. [[YouWouldntLikeMeWhenImAngry It won't end well]].
* BewareTheNiceOnes: The villains of the series often mistake Jaimy's being a gentleman for being weak.
* EvenTheGuysWantHim: Clementine's father and a few others.
* FirstGuyWins: He and Jacky fall in love in the first book and somehow manage to maintain their devotion right until the very end.
* HeroicBSOD: In ''The Mark Of The Golden Dragon'', after [[spoiler:Jacky gets washed overboard during a typhoon. Leads to him becoming a highwayman to kill the people he sees as responsible.]]
* PrettyBoy: A number of girls remark on how beautiful/pretty he is.
* SanitySlippage: Starting with his head trauma in ''My Bonny Light Horseman''.
%%* SweetOnPollyOliver: Was he ever happy to find out Jacky was a girl.
* TookALevelInBadass: In ''Mississippi Jack'' Also in ''Viva Jacquelina'', [[spoiler:where he learned bojutsu from a Shaolin monk]].

'''Joseph Jared'''
%%* FieldPromotion followed by YouAreInCommandNow
%%* HandsomeLech

'''Randall Trevelyne'''

Amy's elder brother
* ChivalrousPervert: He steals a kiss from Jacky and tries to take things further, but backs off when she tells him she's in love with someone else.
* HandsomeLech

'''Jean-Paul de Valdon'''
* EverythingSoundsSexierInFrench

'''Flaco Jimenez'''
* LatinLover: At least, one of the hopefuls.
* LoveableRogue
* {{Pirate}}

'''Captain Richard Lord Allen'''

A charming, rakish British cavalry officer who helps Jackie out of a couple of bad spots
* ChivalrousPervert: While he absolutely will not shut up about how much of a good idea it is to sleep with him, he will not take advantage of a helpless or reluctant woman, as Jacky learns when he catches her at a vulnerable moment.
* FirstNameBasis: Insists (despite his birth) that Jaimy regard him "Richard" or "Dick".
* TheyCallMeMisterTibbs: Insists that Flashby call him "Lord Allen" in a clear showing of disdain.

'''Cheng Shih'''
* ChinesePeople: No, she doesn't count as an AnimeChineseGirl.
* HistoricalDomainCharacter: Based on real-life Chinese pirate Zheng Yi Sao, who personally commanded a fleet of 24 ships and over 1400 pirates.
* IWantMyBelovedToBeHappy: She lets Jacky go with Jaimy, even though [[spoiler:[[LesYay Jacky promised to stay with her forever]].]]
* NamesToRunAwayFromReallyFast: Make no mistake: Cheng Shih is a serious pirate who will not hesitate to sink a ship with all hands aboard, and has a fearsome reputation in the South China Seas because of it.
* PirateGirl: Cheng Shih is aged down from her real-life counterpart (who started marauding in her thirties) to be closer to teenage Jacky's age, though she's still around her early twenties--not quite a girl, but definitely a pirate.

!Jacky's Crews

'''Mr. John Higgins'''

Jackie's loyal manservent and fellow Naval Intelligence operative.
* AmbiguouslyGay: While never stated outright, there's a few references to a personal "secret" that could make things difficult for him, a few "companions" or close male friends in his past, and Jacky's trust in allowing him to hang around even in intimate or compromising moments coupled with Higgins's complete neutrality toward her charms.
* BattleButler: Constantly [[GunsAkimbo dual-wielding percussion cap pistols]].
* TheJeeves: Often providing moral guidance to his wayward Jacky while brushing or washing her hair.
* ServileSnarker: When you hang out with Jacky, sometimes you have to be.

'''Liam Delaney'''

Seaman, rated able.
* PapaWolf: For not only his especial ship's boy Jacky, but for the rest of the ship's boys.
* TeamDad: He's Jacky's "sea dad" in the first book, acting as a mentor to her on the ship.

'''Máiread Delaney'''

Liam's headstrong daughter
* FieryRedhead: Classic Irish beauty with the temper to go along with the hair.
%%* IAlwaysWantedToSayThat: "Stand and Deliver!"

'''Clementine Amaryllis Jukes'''
* FirstGirlWins [[spoiler:Sorry, Clemmie. Jacky got there first]]

'''Jemimah Moses'''
* FryingPanOfDoom

'''Enoch Lightner'''
%%* BlindMusician: Lost his sight in battle.
* DisabilitySuperpower: He can tell how well the sails are drawing by touching the rigging.

'''Ravi'''
* StreetUrchin: How Jacky finds him. Even when he's off the streets, he still can't help but revert to the meek, timid behavior he used to survive.
%%* SurvivalMantra: "Happy puppy, happy puppy, happy puppy..."

! The Rooster Charlie Gang

'''"Rooster" Charlie Brewster'''
* [[AFatherToHisMen A Father To His Gang]]: Unlike many other gang leaders on the London streets, Charlie makes a point of looking after his young charges and protecting them from worse dangers.
* FieryRedhead: Part of the reason he earns the name "Rooster" is his floppy red hair and his wicked temper.

'''Polly Von'''

'''Hugh the Grand'''
* GentleGiant: Though still technically a child, Hugh is over six feet tall and strapping, but is sweet, slow-witted, and slow to rile.
* HugeGuyTinyGirl: Hughie & "Little Mary" were a team, with Mary Faber [[ParrotPetPosition riding on his shoulders]]

'''Joannie Nichols'''

!Naval Intelligence

'''Sir Thomas Grenville'''

First Lord of the Admiralty. Considers Jackie a jumped-up guttersnipe who doesn't know her place, a scheming trollop at best and an out-and-out criminal at worse. He also seems to regard her desire to marry Jaimy an affront to his entire social class. But as she is also a very effective, if frequently exasperating, secret agent, he keeps punishing her by giving her new missions.

'''Mr. Peel'''

Grenville's chief of Naval Intelligence. Considers Jackie a rare treasure -- a tough, intelligent, competent urchin with the veneer of a cultured lady -- and does whatever he can to retain her services. Not that he has her best interests in mind.

'''Carr and Boyd'''

Peel's enforcers, who show Jackie no mercy but also no particular ill will.

'''Henry Flashby'''

A treacherous Naval Intelligence operative who hates Jackie with a passion after she made a fool out of him in ''Mississippi Jack''.

* AmusingInjuries: A face full of bug bites and a butt full of rock salt, amongst other things.
* ColdBloodedTorture: Holds his cigar to Jacky's leg after making her think he was going to blind her with it.
* ObstructiveBureaucrat: Uses his position and contacts in London as well as some good old-fashioned perjury to ensure that Jackie stays in trouble with the law.
* SmugSnake: The smuggest imaginable.
* WouldHitAGirl: Though not as bad as Bliffil, as he prefers slaps to fisticuffs. He also enjoyed torturing Jacky for entertainment and burning her with a cigar, as well as beating his prostitutes in ''The Mark of the Golden Dragon''.

'''Alexander Bliffil'''

A right piece of work. First met bullying the other midshipmen aboard ''HMS Dolphin'', where he soon cultivates an intense hatred for our heroine. Put ashore for cowardice by the end of the first book, he gravitated to Naval Intelligence, where his thuggish tendencies are better appreciated. He takes great pleasure in dragging Jackie back in whenever Peel requires her services, especially if he can give her a few lumps in the process.

* TheBully: Bullies not only the other middies but the young ship's boys.
* WouldHitAGirl: Albeit unwittingly, since he doesn't ''know'' Jacky's a girl. But he's still willing to beat up on someone much smaller than he is.
** He is perfectly fine with beating Jacky knowing she is a girl in ''The Wake of the Lorelei Lee'' for the damages to his character and body suffered by her hand.


! Other Adversaries

'''Mike Fink'''

''The'' Mike Fink: Six and a half feet and fully three hundred and fifty pounds of pure bluster. The biggest, baddest, roughest, toughest keelboat man on the Mississippi, to hear him tell it, and he may not be wrong.

* BadassBoast: Many of the Tall Tales surrounding Mike Fink are his own invention, it seems.
* BarBrawl: Immediately upon setting foot in Pittsburgh.
* CatchPhrase: "I'm a ring-tailed roarer!"
* LargeHam: Part of his schtick. As Jacky learns, sometimes a bit of roaring and playing up his own reputation can get him out of situations that might otherwise defeat him.
* PublicDomainCharacter: A real person who was legendary in his own time as a river boatman and brawler on the Mississippi. While no one's quite sure if he did half the things he was alleged to have done, his presentation in the book is pretty accurate to the way he's known in folklore.
* SquashMatch: Between him and Jaimy.

!Outright Villains

'''Captain Scrogg'''

Demented Captain of the ''Wolverine'' who promotes Jackie to Lieutenant, puts the rest of his officers overboard, and tried to rape her in his cabin. Fortunately for our heroine his heart is not up to the task his loins set for him.

* AttemptedRape: Once he discovers Jacky's female, he wastes no time taking her for his own use. [[spoiler:She only escapes his bed due to a well-timed heart attack.]]

'''Ruger'''
* LoonyFan: He's read the Bloody Jack [[ShowWithinAShow novels]], and identifies Jacky by her tattoo.
* StalkerWithACrush