Every Main Dexter Villain, Ranked By Awfulness

SPOILER WARNING: The following list contains SPOILERS for the first eight seasons of Dexter and Dexter: New Blood. Do not give into your Dark Passenger and read on unless you are completely caught up.

The Dexter: New Blood season one finale gave us the ending to the killer Showtime series we deserved and a new, bloodcurdling adversary in Kurt Caldwell. Yet, how does Dexter: New Blood cast member Clancy Brown’s deceptively deadly character measure up to the other Dexter villains with a multi-episode arc in terms how truly and deeply evil they are?

The following are my choices for the main antagonists from every season of Dexter who most deserved to get a taste of their own medicine from Michael C. Hall’s titular “hero,” ranked from being pretty bad to the absolute worst. We shall start with the lesser of nine evils, whose beef with Dexter came from a more personal and unusually empathetic source. 

By Jason Wiese

After killing his business partner (also his secret boyfriend), Dexter Morgan sparked a vengeful cat and mouse game with Koshka Brotherhood leader Isaac Sirko (Ray Stevenson) that evolved into an unlikely alliance. By kidnapping Dexter’s girlfriend Hannah McKay (Yvonne Strahovski) to add leverage, Sirko offers the killer a truce in exchange for protection from assassins hired by his associate, George Novikov (Jason Gedrick). However, Sirko does succumb to Novikov’s bullet, but not before earning Dexter’s respect with some sound relationship advice.  

Almost like his relationship with Isaac Sirko in reverse, Dexter finds an unexpected friend in Assistant District Attorney Miguel Prado (Jimmy Smits) after murdering his brother, Oscar. Prado reveals he has homicidal tendencies of his own, convincing Dexter he may be worthy of learning Harry’s Code until he breaks it by killing a corrupt, but otherwise innocent, rival attorney. Realizing he has unleashed an unstoppable, self-serving monster who could also use his power to ruin Dexter’s life, he kills Prado and later asks his adoptive sister, Debra (Jennifer Carpenter), to take his place as “Best Man” when he marries Rita (Julie Benz).

Dexter and Rita’s ill-fated romance was put on hold in Season 2 after she, mistaking his killing spree for a drug habit, enrolls him in rehab where he finds a sponsor in Lila West (Jaime Murray), who becomes a home wrecker after Rita suspects Dexter cheated with her. This actually leads Dexter to pursue a real relationship with Lila, until her infatuation grows and she conspires to keep him for herself by resorting to her dark, manipulative tendencies - most notably pyromania. While causing the explosive death of Sgt. James Doakes (Erik King) at least prevented Dexter from becoming a Bay Harbor Butcher suspect, vengefully trapping Rita’s kids (Christina Robinson and Daniel Goldman) in a fiery blaze is unforgivable.

On the 2021 series revival, Dexter also had to save his own biological son, Harrison (Jack Alcott), from the elusive Kurt Caldwell (Clancy Brown), whom you initially feel bad for after Dexter breaks his decade-long no-killing streak on his repulsive adult son, Matt (Steve M. Roberston). However, the truck stop owner arouses suspicion by claiming his son is alive, which turns out to be a ruse to keep authorities away from his secret cabin where he holds young women captive before sniping them to death. The most disturbing step of his obsessive, fetishized ritual: underneath his cabin lies a well-kept gallery of his many victims’ taxidermied remains.

A killer who never hid his victims and, instead, repurposed them as symbolic warnings of the impending Apocalypse was Travis Marshall (Colin Hanks) - another Dexter villain who initially earns your sympathy as the supposedly reluctant pupil of murderous religious fanatic, Professor James Gellar (Edward James Olmos). However, when Dexter finds Gellar’s corpse in a freezer, the Fight Club-style twist causes Marshall to fully embrace his darker nature and wage personal war on Dexter that goes as far as taking baby Harrison hostage as he continues his increasingly grotesque, inhumane, and biblical-themed tirade. Seeing Dexter send the delusional, morally misguided psycho to his maker might have been even more satisfying if Deb hadn’t caught him in the act.

Speaking of Deb, the scum behind her heartbreaking death is the cold-blooded, unfeeling sadist Oliver Saxon (Darri Ingolfsson) - dubbed “The Brain Surgeon” for the missing scoops of brain found in his victims by Miami Metro, who consult Dr. Evelyn Vogel (Charlotte Rampling) for help. The specialist reveals herself as the proud co-creator of Harry’s Code to Dexter, whom she also asks for help when she suspects the Brain Surgeon is a former patient after receiving the aforementioned missing brain scoops at her doorstep. However, Dexter eventually identifies him as Vogel’s long-lost son (real name Daniel), whose first victim was his own brother, Richard, when he was just a child.

The first person to capture Dexter’s heart after Rita’s murder (which we will get to soon) is Lumen Ann Pierce (Julia Stiles), who catches him killing Boyd Fowler (Shawn Hatosy). She tells Dexter that Boyd was not her first sexual assailant, eventually leading him to confirm his suspicions about charismatic motivational speaker Jordan Chase (future Elementary cast member Johnny Lee Miller), who is connected to her disturbing past. In fact, he is the secret orchestrator of an entire crew of torturous serial sexual predators referred to as the Barrel Girl Gang for how they disposed their victims, making him one of the most frightening depictions of a sexual abuser in fiction.

Dexter’s first “big bad,” dubbed “The Ice Truck Killer,” is also one of his most frightening, let alone the most personal since he is really his biological older brother, Brian Moser (Christian Carmago). The shocking discovery actually makes killing the horrifying murderer an upsetting decision for him. However, considering his modus operandi (delicately draining victims’ blood and preserving the remains in the eponymous refrigerated transport) and the fact that he posed as Deb’s doctor before proposing marriage to her and attempted to convince Dexter to kill her himself, he certainly fit the code.

There is a reason why most fans (myself included) believe Dexter Season 4 is the series’ masterwork and his name is John Lithgow, who earned a well-deserved Emmy for disappearing into his startling performance as Arthur Mitchell. Dexter is at first intrigued by the “Trinity Killer’s” ability to balance his deadly spree with his life as a husband and father (something he is struggling with himself), until it becomes clear that his own family is terrified of him. Dexter is the last man standing in their epic showdown, but is too late to protect Rita from Mitchell and discovers her floating in a bathtub filled with her own blood.

Dexter Morgan had a wide variety of opposers, some who were just matters of circumstance (such as Isaac Sirko's broken heart) or the result of his own mistake (such as helping Miguel Prado unlock his Dark Passenger). Others were driven by dangerous delusions (Travis Marshall), a traumatic past (Kurt Caldwell), or, simply, pure evil (pretty much everyone else). However, at the end of the day, no matter how sinister each one compares to each, the world had no room for any of them.