Team Templar (and Jeremy)
- Bunny-Ears FBI Agents
- Code Names: Templar, Springheel, Specs, Specs Two, Honda, Texas, Stonewall, and Shadow.
- Deadpan Snarker: Everyone has their moments. Except Stonewall.
- FBI Agents
- Friendly Enemy: With Jeremy. Except for Simon, who's Dating Catwoman instead.
- Ragtag Bunch of Misfits
- True Companions
Simon Drake ("Templar")
- Bi the Way: Leans more towards women in general. Word of God says he's around a Kinsey 2.
- Control Freak: He's accused of this multiple times. Is occasionally willing to admit it.
- Crazy Jealous Guy: Simon doesn't take the revelation that the thief in Double Down is Jeremy's ex-lover very well. At all.
- Dating Catwoman: They're not dating!
- Domestic Abuser: Let's be honest: if Jeremy was female, Simon would be considered an absolutely horrible person, because he very often treats Jeremy like shit and once beat the hell out of Jeremy with serious intent to hurt him and had some very dubiously consensual sex. Although Simon does start getting his act together by the end of the third book.
- Green-Eyed Monster: Simon tends to be very possessive over things he perceives as his, regardless of whether he's willing to consciously admit that he thinks of them that way or not. He gets jealous over Jeremy getting along with his teammates, because they're Simon's team and Jeremy is not one of them and never will be. Of course, he then proceeds to get incredibly, bitterly jealous over Jeremy's rival/ex-lover/"brother" Bran and is also (momentarily) jealous of Annabelle when Jeremy is comforting her after she's rescued. Simon even shows hints of being jealous of Johnny, of all people, in High Fidelity when Johnny and Jeremy are off discussing things in the gazebo.
- Jerk with a Heart of Gold
- The Leader: Has elements of all four types, but mostly III and IV.
- Married to the Job
- Must Have Caffeine: The coffeemaker in Team Templar's room is labeled "Mrs. Simon Drake (♥)".
- Oblivious to Love: In this capacity Simon may be borderline retarded.
- Only Sane Employee: Well, he does run a team of lunatics.
- Papa Wolf: Toward his squad.
- Team Dad
- Tranquil Fury: When Farraday kidnaps Jeremy.
- Tsundere: Type A to an almost ridiculous degree with Jeremy.
Sandra Leone ("Springheel")
- Action Girl: Her character profile even notes that one of her roles is to be the "muscle". She's very good at smacking people around. Including her teammates.
- Blue Blood: She did try to be the kind of upper-class daughter her parents expected her to be...but she got bored with that and joined the FBI.
- Green-Eyed Monster: With Mike and Diana Fontaine. Shows hints of it in With a Bullet when talking to Jeremy about Simon; she's quite nasty to Jeremy when he shows up, even though she was the one who called him in the first place.
- The Lancer
- Mama Bear: Toward her teammates.
- Number Two: Which causes some friction between her and Simon later on, as twice she has to take over for him as the leader of the team; once when he's out of commission and again when he's suspended from active duty. It's difficult to go back to being second-in-command after that.
- Only Sane Agent
- Time to Step Up, Commander: When Simon is taken out of commission by Farraday at the start of With a Bullet, Sandra is very stressed out over having to take Simon's place. When Mike tries to give her a pep talk, she hits himnote . The second time she's put in charge, she's much more sure of herself, but still hesitant because of the complexities it could raise when/if Simon returns.
- The Smurfette Principle: Poor lonely Sandra...
- Took a Level in Jerkass: In the last two books, she takes a level whenever she's dealing with Jeremy, most notably in High Fidelity, where she almost always seems to be about five seconds away from ripping his throat out with her teeth.
Nate Waxman ("Specs")
- Break the Cutie: Shows signs of past breakage during With a Bullet, but on the whole he's managed to recover.
- Captain Crash: To the point of it being an acknowledged Running Gag.
- The Chick
- No Sense of Direction: He was the only one who managed to get lost inside of an opera house (and twice, at that). Please note that he was also the only member of the team who had actually been there before.
- Scars Are Forever: His chest is covered with scars from when Farraday pinned him down and sliced him up with a knife.
- Stuff Blowing Up: He is the team's explosives expert. On Team Templar, this is a position that more often requires him to make bombs than defuse them.
- Team Mascot: As dubbed by Simon.
Mike Takemura ("Honda")
- Ambiguously Brown/But Not Too Foreign: Invoked. His father was Japanese-American and his mother was Hispanic, giving him a general "ethnic" look. It's been used to the team's advantage in a number of undercover operations.
- The Big Guy: Shares this role with Johnny.
- Boisterous Bruiser
- Drives Like Crazy: Takes it to new levels with just as much glee as he shows while jumping on Double Entendres.
- Handsome Lech
- Pungeon Master: He is often kicked preemptively because the others know what's coming.
- Team Chef
Johnny Pilgrim ("Texas")
- Addiction Displacement: Swapped cigarettes for toothpicks.
- Beware the Quiet Ones: "Some people just need killing."
- The Big Guy: Shares this role with Mike.
- More Dakka: Johnny can always be counted on to have a shitload of high-caliber weaponry and the ability to kill things with it. And grenades.
- The Stoic
Rich Story ("Specs Two")
- Insufferable Genius: He is the best at what he does and he will make sure that you know that.
- Jerkass: Sandra (mentally) describes him as an "ill-tempered little asshole with almost no sense of humor". Even Simon, who actually considers him a friend, once calls him "a very shouty little man", much to Jeremy's amusement.
- Irrational Hatred: Jeremy seems to be very good at inspiring this in people. Rich certainly has good reason to dislike Jeremy, but the raw hatred he displays is...excessive, to say the least.
- Killed Off for Real: By Simon, no less.
- The Friend Nobody Likes: Really, Simon's the only one who actually likes him.
- The Mole
- Too Clever by Half: What causes his downfall; he was tricked into posting a confidential memo to prove that he could crack it, and Karpol began blackmailing him.
Dave Brassoff ("Stonewall")
- Bunny-Ears Lawyer: Specially mentioned because Jeremy assures Dave that he's actually the right kind of crazy to fit in with Team Templar—all Dave needs to do is grow a spine. Which he does. Epically.
- Dissonant Serenity: In a Zen state while working on the computer. Mouse pad suddenly on fire. Dump coffee on it without sparing it a glance. Continue programming.
- Forgets to Eat: And sleep.
- New Meat: A textbook case until the end of With a Bullet.
- Replacement Scrappy: In-universe, for Rich Story.
- Workaholic: While otherwise capable of working on a normal schedule, Dave will go into overdrive when he's given a specific task, pulling all kinds of lunatic hours to get the job done. His current record is thirty-five hours straight without going home.
Jeremy Archer ("Shadow")
- Abel: To Bran's Cain.
- The Atoner: According to Word of God, he holds himself responsible for the wedge between Bran and Ethan, and has spent years trying to get Bran to reconcile with Ethan. It's so important to him that he considers death an acceptable price to pay for the chance of that reconciliation.
- Because I'm Good at It: Why he enjoys being a thief so very, very much.Jeremy: I thought you of all people might understand that nothing is more fun than doing that at which you excel.
- Becoming the Mask/That Man Is Dead: Jeremy Archer is, according to Word of God, just a façade. Jeremy abandoned his original self and took on the identity that Ethan gave him as his "main" and "real" identity from that point on, modelling himself after his foster father so as to leave who he was behind. See "Generation Xerox".M. Chandler: And, let us be frank, Jeremy Archer is a construct. A successful one, yes, and one that is second nature by now, a real human being in his own right, but still, essentially, a carefully-crafted façade built around the heart and bones of a neglected and needy little boy.
- Bi the Way: With a preference toward men. Word of God says he falls around a Kinsey 4.
- Classy Cat-Burglar: Interestingly, with the Spy Catsuit and Dating Catwoman, he's a Rare Male Example of a trope with a Distaff Counterpart.
- Code Name: Notable in that he didn't choose it; it was assigned to him years ago by Art Theft.
- Con Men Hate Guns: Over the course of the entire series, Jeremy handles a gun on only two occasions: once when Simon is giving him lessons in the firing range, and once when he uses Simon's gun to kill Farraday. It causes him to have a Heroic BSoD, even though he only shot Farraday when it became clear that Simon would be killed if he didn't.
- Death Seeker: He shows shades of this. It's confirmed by Word of God.
- Desperately Craves Affection: Due to his backstory; it's the main reason he puts up with so much abuse from Simon.
- Foster Kid: Ethan's foster son. Unlike most examples of this trope, Ethan is a good* and loving parental figure.
- Generation Xerox: A strange, deliberate example. When Simon meets Ethan, it becomes apparent that Jeremy has modeled himself after his foster father—not only in terms of his career, but also style, mannerisms, speech patterns and Drink Order. There's a good reason for this; see "Becoming the Mask".
- Gentleman Thief
- Happily Adopted: At age fifteen by Ethan. Well, not officially adopted, but that's just a technicality.
- Karma Houdini: Part of being the best thief in the world means never getting caught, after all.
- Love Martyr: See "Domestic Abuser" under Simon's heading. There's also the situation with Bran. Jeremy's willingness to put up with incredible amounts of shit is mainly the result of being so starved for affection and love as a child.
- Loveable Rogue: Sure, he's a criminal, but he's a smooth operator and has no interest in physically harming anyone.
- "Mission: Impossible" Cable Drop: He's very fond of these. Using suction cups.
- No Sense of Personal Space: Employs this with Simon. All the time.
- Not a Morning Person: As Simon finds out in Double Down.
- Perpetual Smiler/Stepford Smiler: In High Fidelity, Simon notes that Jeremy's customary smile is basically the same as Jeremy having no expression at all.
- Phantom Thief: He didn't earn the name "Shadow" for nothin'.
- Rentboy: How Jeremy got by before Ethan took him in.
- The Sixth Ranger
- Spy Catsuit: Slick and skintight. Simon approves. Nate blushes.
- Stealth Expert
- Cain: To Jeremy's Abel.
- Cluster F-Bomb: He can be very verbose.
- Evil Counterpart: To Jeremy. They're both criminals, but Jeremy's a Gentleman Thief and Bran's an unrepentant murderer.
- Funetik Aksent: Played with; the way he pronounces words (Jaysis!) is mentioned in the prose, but it's heavily downplayed in his actual dialogue.
- Freudian Excuse: He blames all of his worldly problems on Jeremy, because Jeremy "stole" what was rightfully Bran's. Which isn't true, and Jeremy lampshades just how ridiculous a thing that is to say regardless.Jeremy: Not to belabor the obvious, but I am a thief. In fact, I'm the best thief in the world. And you're not.
- Hair-Trigger Temper: He can and probably will take offense to anything and everything, but especially Jeremy's existence.
- In-Series Nickname: Jeremy calls him "Irish" because...well, because he is.
- Irrational Hatred: Jeremy used to find it hurtful; at this point, it's still hurtful, but also extremely exasperating.
- Karma Houdini: A very ungentlemanly thief, murders innocent people, attacks Simon's team with intent to kill, tries to shoot Jeremy in the back, and made choices in life which greatly saddened and disappointed his father. Yet at the end of the series, he's about twenty-five million dollars richer, presumed dead by everyone save for a few select people, and will never have to work another day for the rest of his life if he so chooses.
- Nervous Wreck: Jeremy notes (and Bran later demonstrates) that Bran tends to dissolve into a panicked state of fight-or-flight when things don't go according to plan.
- The Unfavorite: Subverted. Bran is wholly convinced that he is this, but Ethan and Jeremy make it clear that it's very much not the case.
"Colonel" Cole Farraday
- Hair-Trigger Temper
- I Have Your Wife: Manages to get the drop on Jeremy of all people with a Taser, and eventually calls Simon to ask if Simon's "missing something". Of course, Jeremy being who he is, Farraday didn't have much hope of holding onto him once Jeremy woke up.
- Insane Equals Violent
- Killed Off for Real
- Mood-Swinger: Swings between "calm" and "frothing-at-the-mouth psychotic" at the slightest provocation, and it's genuinely frightening.
- Obfuscating Insanity: It was suspected that he used this to be discharged from the army, but if he wasn't crazy before going to prison, he certainly was when he got out.
- Speech Impediment: Along with physical tics, he stutters very badly. It gets worse when he loses his temper.
- Thou Shalt Not Kill: Not because he doesn't want to, but for practical reasons; the instant you murder someone, it's game over as far as the legal system is concerned. He abandons this philosophy by the end of With a Bullet, but Jeremy kills Farraday before Farraday has the chance to murder Simon.
- Deadpan Snarker
- Drives Like Crazy: According to her character profile.
- Iron Lady: Hell yes.
- Passive-Aggressive Kombat: Engages in this with Simon.
- The Woman Wearing The Iron Lady Mask: Started out this way in her career.
- Becoming the Mask: It stopped being a mask long before Simon meets her.
- A Pupil of Mine, Until He Turned to Evil: Bran, naturally. But Ethan still loves him, because Bran is his son.
- Cool Old Guy
- Deadpan Snarker: Oh, is he ever.
- Criminal Counterpart: To Upstairs. Both Ethan and Upstairs are very trusting and protective of their charges (Jeremy and Simon, respectively), will bend rules to help them, have a lot of resources at their disposal, and both act as father figures.
- Good Father: To both of his foster/adopted sons, though Bran is somewhat less appreciative of it than Jeremy.
- Karma Houdini: As far as we know, Ethan was never caught.
- Retired Gentleman Thief: He's technically not even wanted for anything anymore; the statute of limitations for all of his crimes has run out. Of course, this doesn't mean that he doesn't do illegal things at all anymore. He's just retired from his main profession.
Upstairs (Warren Carstairs)
- Benevolent Boss
- A Father to His Men: Most obviously with Simon.
- In-Series Nickname: Simon (and everyone else) calls him Upstairs.
- Law-Abiding Counterpart: To Ethan. Both Upstairs and Ethan are very trusting and protective of their charges (Simon and Jeremy, respectively), will bend rules to help them, have a lot of resources at their disposal, and both act as father figures.
- Reasonable Authority Figure: Very, very much so.
- Answering Service: She answers the phone and takes messages for Jeremy, in addition to being the person he calls if he needs to leave somewhere fast. She's usually not involved in the actual jobs so much, though.
- Classy Cat-Burglar: She used to be one.
- Handicapped Badass: She's in a wheelchair, but that doesn't stop her from helping keep the mooks away during her rescue.
- Missing Answering Service: The catalyst for the second-introduced major plot of High Fidelity.
- The Voice: She's just a voice over the phone until High Fidelity.