Death Brackets: Toughest Dicks vs. Baddest Thriller Heroes: First Round, Part 1

Death BracketsIf you’re not up to speed on the concept and the competitors, here’s where we set the rules and the brackets. Eight of the world’s best detectives versus eight spies, assassins and anti-heroes in a fight-to-the-death contest of wits and toughness. In brief, each hero is dropped into a random setting — not their home turf — at least five miles away from the other. Each has an explosive charge with a keypad strapped to their ankle. The explosive has a timer, counting down for three days, along with the engraved numbers that will disarm the other man’s device.

They also have a photo of the opposition. Who’s better at hiding? Who’s better at hunting? Finishing off the competition?

Here’s our first matchup, inlcuding the most famous master detective of all versus an iconic super-spy.

1) Battleground: Detroit


Sherlock Holmes

– if you don’t know this champ, you’ve been under a rock. Cornerman: Arthur Conan Doyle


 – Spy introduced in 1965’s, The Berlin Memorandum. Cornerman: Adam Hall aka Elleston Trevor

Pros World-class brainy genius. Master of disguises.  Can go without eating for days. Versatile with weaponry plus Japanese system of baritsu used to defeat Moriarty at Reichebach (“The Adventure of the Open House”)  Expert in shotokan karate and chin na, the manipulation of joints. Unafraid of death. Accustomed to living in tough conditions, unlike 007, parachuted into Poland and impersonated a concentration camp guard for three years to gather intelligence.
Cons Arrogant. Bit of a drug addict. Used to having money for tobacco, cocaine, and occasional morphine. Doesn’t like guns, though used them in WWII. “…tense, edgy and bitten-eared … he is a professional neurotic, half in love with death.”
Vegas Line Better action-hero moves than commonly thought, can wean off hard stuff. Under-rated, really. And he’s necessarily excellent at unarmed combat.


Outcome: Holmes gets a nine millimeter from the streets, disguises himself as a homeless person and gets a network of street people to serve as his eyes and ears, like the Baker Street Irregulars — and he catches Quiller off-guard. A single shot to the middle of Quiller’s chest and it’s over.

Current Score:
Master detectives, 1 / Spies, assassins, anti-heroes, 0.


2) Battleground: Fishing Village in Quinlon, India


Mike Hammer

– Archetypical hard-boiled detective from 1947, brutal, self-described misanthrope. Cornerman: Mickey Spillane


 – Joined Secret Intelligence Service prior to WWII. Saw action in Germany, Switzerland and Sweden. Cornerman: John Le Carré

Pros No softer side. A soldier who survived the Battle of Guadalcanal. Quick with his fists and an expert with his .45, which he nicknamed Betty and carries in a shoulder holster. No moral qualms whatsoever.  Described by commanders as having “the cunning of Satan and the conscience of a virgin.” A veteran’s veteran. Knows everything about tradecraft and the spy business. Unlike Bond, uses brains instead of his fists or gadgets.
Cons Not the most subtle or elegant of brains. His toughness is partly fueled by uncontrollable rage. Not just quiet and middle-aged, described as short and fat. Not especially fit.
Vegas Line If this is a boxing match, or a shooting competition, he wins. If it’s a chess match, he’s gone. Unless he completely outwits his opponent, he may be in trouble.


Outcome: Both men are fish out of water here. They don’t know the local language. As white men, they stick out. Smiley is less fit physically, but more fit mentally for the challenge. He adapts, dresses like a local, acts like a local, talks to the locals who speak English—and catches Hammer asleep under a bridge. Once more, teamwork beats going it alone.

Current Score:
Master detectives, 1 / Spies, assassins, anti-heroes, 1.


3) Battleground: A Deserted Island Off The Coast Of Guam


Jack Reacher

– 6’5 ex-Army investigator with ties to no one. Goes simply by “Reacher.” Cornerman: Lee Child

Jack Ryan

 – former Marine who became a stockbroker and made millions before joining the CIA. Cornerman: Tom Clancy

Pros Experienced at figuring out where people might hide. Improvisation is also a strength. Expert sniper. Fast and practical when it comes to unarmed combat. Thoughtful and strategic, always thinking four or five moves ahead. Proves his worth in a scrap. Speaks multiple languages. Harrison Ford played him in two movies.
Cons Stands out in a crowd, making it harder to hide. Slow runner. Severe back injury from a helicopter crash left him with a permanent disability, a back brace and a close call with addiction.
Vegas Line If  contest drags on all three days, will need to eat and drink to keep  big body going. A desk jockey at heart, and even the best desk jockey in the world is still a desk jockey.


Outcome: No weapons here, unless you make them yourself. Ryan figures it’s smarter to sleep during the day and hunt at night. Reacher decides to hunt day and night, figuring he can stay up at least 24 hours. And he can. He easily wins the Battle of the Jacks by head-butting a surprised and sleepy Ryan and breaking his already-weakened back with a crushing bear hug.

Current Score:
Master detectives, 2 / Spies, assassins, anti-heroes, 1.


4) Battleground: Juneau, Alaska


Phillip Marlowe

– Prototypical hard-working, hard-drinking private dick. Cornmerman: Raymond Chandler


 – Serial killer who hunts other serial killers. Doesn’t consider himself human. Cornerman: Jeff Lindsay

Pros A highly experienced killer who knows all about trapping other dangerous killers. Quite careful and methodical. Always prepares well in advance and sets up the time and place that  he’ll strike.  At 6-foot and 190 pounds, good at getting people to talk. Not the Neanderthal machine of rage and vengeance that Hammer is—a more thoughtful tough guy, with a thing for poetry. Known to carry a nine-millimeter Luger or a .38.
Cons Has a fully functional moral code. Animals don’t like Dexter—dogs bark at him.
Vegas Line This isn’t a methodical contest. The other man knows he’s being hunted. Chess player, so apt to think several moves in advance when strategizing.


Outcome: Marlowe gets smart and adopts a dog, to warn him before Dexter gets close. Dexter gets smarter and waits in the parking lot of the Juneau-Douglas Humane Society. Marlowe is dumped into the cold, Pacific Ocean one piece at a time.

Current Score:
Master detectives, 2 / Spies, assassins, anti-heroes, 2.

Next post: the last four matches of the First Round

Detroit image via Adam Jones.

Guy Bergstrom is a speechwriter and former reporter who also writes for the NYT’s as their expert on public relations and publicity. His first novel, TEN DAYS, was a 2011 finalist for best mystery-thriller at PNWA. You can pick literary knife fights with him @epicblackcar on Twitter.


  1. Clare 2e

    So, no one who guessed from the intro saw all four matches exactly like Guy did. Most people picked Mike Hammer to beat Smiley.
    Still, the winners are: Sherlock, Smiley, Reacher and Dexter!

    And of our original handicappers, Gram came the closest to getting this set of matches right, except he’d picked Marlowe over Dexter. Congrats, Gram! 3 out of 4 ain’t bad.

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