In the golden age of modern television sitcoms, few holiday traditions rival the chaotic, double-crossing, smoke-bomb-filled brilliance of Brooklyn Nine-Nine’s Halloween Heists.

What began in Season 1 as a petty bet between Detective Jake Peralta (Andy Samberg) and Captain Raymond Holt (Andre Braugher) rapidly evolved into the precinct’s annual battlefield of psychological warfare. Over eight seasons, the rules expanded, alliances shattered, lookalikes were hired, and items of arbitrary value—from Holt’s Medal of Valor to an illuminated championship cummerbund—were stolen in increasingly unhinged operations.

Following our countdowns of Andy Samberg’s best comedy work and our retrospective on The Office’s greatest Halloween episodes, the Halloween Heists remain the creative high point of Dan Goor and Michael Schur’s beloved police sitcom.

Here is the definitive ranking of every Brooklyn Nine-Nine Halloween Heist episode, ranked from worst to best based on plot twists, comedic payoffs, and emotional resonance.

Every Brooklyn Nine-Nine Halloween Heist at a Glance

  ★ 1. Season 5, Episode 4: "HalloVeen" — The Proposal Masterpiece
  ★ 2. Season 1, Episode 6: "Halloween" — The Origin & Medal of Valor Bet
  ★ 3. Season 2, Episode 4: "Halloween II" — Holt's Total Squad Takeover
  ★ 4. Season 3, Episode 5: "Halloween III" — Amy Outsmarts the Arrogance
  ★ 5. Season 4, Episode 5: "Halloween IV" — Gina Linetti & Cheddar the Corgi
  ★ 6. Season 8, Episodes 9–10: "The Last Day" — The Emotional Series Finale Heist
  ★ 7. Season 6, Episode 16: "Cinco de Mayo" — Lieutenant Terry's Long Game
  ★ 8. Season 7, Episode 11: "Vallowen" — The Three-Holiday Chaos

8. Season 7, Episode 11: “Vallowen” (Season 7)

  • The Winner: Rosa Diaz
  • The Target: Three Infinitude Gems (gems locked in a cheddar bunny)
  • Why It’s #8: Hampered by real-world scheduling and plot contrivances, the heist was delayed from Halloween to Valentine’s Day, and ultimately to Easter. While Rosa proving her tactical supremacy by jumping off the precinct roof into a dumpster is classic Rosa badassery, the fractured three-holiday timeline robbed the heist of its trademark October momentum.

7. Season 6, Episode 16: “Cinco de Mayo” (Season 6)

  • The Winner: Terry Jeffords
  • The Target: Scully’s Medical Alert Bracelet
  • The Twist: Delayed from Halloween because of a precinct bomb threat, the squad moves the competition to Cinco de Mayo to distract Terry from his stressful Lieutenant’s exam.
  • The Payoff: In reality, Terry had already passed his exam weeks earlier and orchestrated the entire fake panic to keep Jake and Holt off balance. Watching Terry declare himself “The Ultimate Detective/Genius” while eating yogurt is pure joy.

6. Season 8, Episodes 9–10: “The Last Day” (Season 8)

  • The Winner: The Nine-Nine
  • The Target: A Medal of Valor stored in a customized safe
  • The Farewell: Serving as the two-part series finale, this heist brought back beloved guest stars like Gina Linetti (Chelsea Peretti), Adrian Pimento (Jason Mantzoukas), and Mlepnos (Fred Armisen).
  • The Emotional Weight: Rather than being about petty ego, Jake designed the heist as a secret farewell ceremony before retiring to become a stay-at-home dad. Holt confessing to Jake that if he had a son, he would have wanted him to be like him remains one of the most touching moments in modern sitcom history.

5. Season 4, Episode 5: “Halloween IV” (Season 4)

  • The Winner: Gina Linetti
  • The Target: A plaque locked inside a glass case
  • The Chaos: The first year the squad officially divided into teams. Holt and Terry recruit Holt’s beloved Pembroke Welsh Corgi, Cheddar, while Jake and Gina attempt optical illusions.
  • The Masterstroke: Gina fakes knocking out her front teeth in a roller-skating accident, allowing her to secretly orchestrate the entire heist while pretending to be an injured civilian.
Cheddar the corgi running through police station hallway with envelope
Captain Holt's prized corgi Cheddar became the decisive secret weapon in Brooklyn Nine-Nine's annual Halloween heists.

4. Season 3, Episode 5: “Halloween III” (Season 3)

  • The Winner: Amy Santiago
  • The Target: A golden crown
  • The Feminist Revenge: Arrogant after winning the first two heists, Jake and Holt treat Amy like an irrelevant pawn, refusing to let her participate as a full rival.
  • The Satisfaction: Sick of their condescension, Amy recruits the janitorial staff, plays Jake and Holt against each other, and snatches the crown from under their noses. Seeing Holt and Jake forced to bow and chant “All hail the Queen” is perfection.

3. Season 2, Episode 4: “Halloween II” (Season 2)

  • The Winner: Captain Raymond Holt
  • The Target: Holt’s wristwatch
  • The Holt Masterclass: Determined to avenge his Season 1 loss, Holt demonstrates the terrifying depths of his competitive pettiness.
  • The Revelation: Jake thinks he’s executing a flawless plan, only to discover that Holt hired a pickpocket, bribed Jake’s bus driver, and orchestrated an elaborate flash mob. Holt delivering his victory speech while wearing a deadpan smirk established the comedic dynamic that carried the entire series.

2. Season 1, Episode 6: “Halloween” (Season 1)

  • The Winner: Jake Peralta
  • The Target: Holt’s Medal of Valor
  • The Historic Beginning: The episode that proved Brooklyn Nine-Nine was not just another generic cop comedy.
  • The Brilliance: Jake betting Holt that he can steal the medal from his locked office by midnight forces the precinct to work together. From Charles dressing up as Mario Batali to Amy wearing an embarrassing nerd costume, this episode locked in the ensemble chemistry that turned the show into a classic.

1. Season 5, Episode 4: “HalloVeen” (Season 5)

  • The Winner: Jake Peralta & Amy Santiago
  • The Target: The Championship Cummerbund
  • Why It’s #1: The undisputed, emotional masterpiece of the entire franchise.

What begins as an ultra-competitive heist featuring severed hand pranks, decoy cummerbunds, and Cheddar the corgi culminates in the greatest television proposal of the decade. When Amy finally locates the championship cummerbund in the evidence locker, she flips it over expecting to see the standard brag:

Instead, embroidered in gold thread, it reads:

“Amy Santiago, will you marry me?”

As Amy turns around in shock, Jake drops to one knee. Blending genuine, tear-inducing romantic intimacy with the show’s signature goofy comedy, “HalloVeen” stands as one of the finest half-hours of comedy broadcast in the 21st century.

Brooklyn Nine-Nine Halloween Heist Champion History

Season Episode Title Target Item Ultimate Victor Key Heist Strategy
S1 “Halloween” Medal of Valor Jake Peralta Precision window climbing & squad distraction
S2 “Halloween II” Holt’s Wristwatch Captain Holt Hiring pickpockets & precinct-wide conspiracy
S3 “Halloween III” Golden Crown Amy Santiago Outsmarting Jake & Holt’s mutual arrogance
S4 “Halloween IV” Plaque in Glass Case Gina Linetti Staging roller-skating dental accident
S5 “HalloVeen” Championship Belt Jake & Amy Secretly swapping belt for marriage proposal
S6 “Cinco de Mayo” Scully’s Med Alert Terry Jeffords Faking Lieutenant exam panic
S7 “Vallowen” Infinitude Gems Rosa Diaz Dumpster diving & Easter bunny deception
S8 “The Last Day” Farewell Medal The Nine-Nine Collective squad tribute to the precinct

Frequently Asked Questions

Who won the most Brooklyn Nine-Nine Halloween Heists?

Technically, no single character won more than once individually. Jake, Holt, Amy, Gina, Terry, and Rosa each won one standalone heist, with Jake and Amy sharing the Season 5 proposal victory, and the entire squad sharing the Season 8 finale win.

Why is the Season 5 Halloween episode so famous?

Season 5, Episode 4 (“HalloVeen”) concluded with Jake Peralta using the championship cummerbund to propose to Amy Santiago, making it one of the most celebrated and emotional proposal scenes in sitcom history.

Is Cheddar the dog in the Halloween Heists?

Yes! Captain Holt’s beloved Pembroke Welsh Corgi, Cheddar, is a recurring secret weapon in multiple heists, famously appearing in Season 4, Season 5, and Season 7.