Oscar Sail

Created by Lester Dent
(1905-1959)

When not busy churning out most of the 181 Doc Savage adventures under the Kenneth Robeson pseudonym, prolific pulpster Lester Dent could produce wild and wacky hard-boiled dicks with the best of them, including Lynn Lash, Lee Nace (The Blond Adder), Foster Fade (The Crime Spectacularist)  and Click Rush (The Gadget Man). They were all very tall, fine young fellows with a penchant for gimmickry and gadgets (one of Dent’s passions).  Their cases tended towards the fantastic, similar to those on Doc’s side of the fence.

OSCAR SAIL was something else again, a more low-keyed, but no less engaging, sort of eye, although in Dent’s world, “low-key” is relative.

According to author/pulp historian Ron Goulart, Dent “had a special reverence for Black Mask” and the few stories he wrote for that magazine were more straightforward, down-to-earth detective fare.  The Oscar Sail capers were arguably the best of these, both appearing within a few months of each other in 1936 — even as the Doc Savage phenom was just starting to gather steam.

Sail was described as “…a long, brown man, dressed in black — black polo shirt, black trousers and black tennis shoes… Weather and salt had not left much color in his hair.”  He worked as a Florida private eye, based in Miami and extremely tall (seven feet?), and had a rather quixotic sense of honor. But in lieu of Dent’s usual gadgets, Sail utilized his quick mind and agile body to solve his rather intense cases.  He lived on a black, 45-foot long (34-foot at the waterline) Chesapeake Bay bugeye anchored in Biscayne Bay, that he humbly christened Sail (boating was another of Dent’s passions).

Hmmm… an agile tough guy, living on a boat docked in Florida. Sound familiar?

There are some definite similarities to John D. MacDonald‘s “salvage expert” Travis McGee, and more than a bit of speculation over the years, but nobody has made a solid case yet. But Lester Dent did write for the pulps throughout their heyday, and John D., one of the last writers to write for them, would definitely have been aware of Dent’s work.

But whatever…

Unfortunately, Dent only left us with two stories about Oscar Sail — he really deserved more outings than that. Well, only two, except…

THE OTHER OSCAR SAIL

• Dent apparently had high hopes for a possible series based around the exploits of the Miami-based detective, but the series never materialized. But for a peek at what Dent had initially intended, check out “Luck,” the original version of “Sail” before Black Mask‘s editors got their hands on it. “Luck” eventually surfaced in 2020, in the Les Standiford’s edited Miami Noir: The Classics (and a year later in The Complete Black Mask Cases of Oscar Sail) and it presents a completely different–but no less devious–Sail. Gone is the long, dangerous physique; instead we get a short man with “round jolly brown features of a… man who probably liked his food.”

UNDER OATH

• “(‘Angelfish’ is) plagued by Dent’s characteristic semi-literate understatement, but it’s for sure a tough story, told with hurricane ferocity. His hero is a tall, lanky detective named Sail, who dresses all in black. The chase is after some aerial photos of a promising oil field. Uncomplicated, in a breathless way.”
  — Steve Lewis (August 2020, Mystery*File)

SHORT STORIES

• “Sail” (October 1936, Black Mask; reprinted in The Hard-Boiled Omnibus; aka “V Marks the Spot”)
• “Angelfish” (December 1936, Black Mask; reprinted in The Hard-Boiled Dicks; aka “Tropical Disturbance”)
• “Luck” (2020, Miami Noir: The Classics)

COLLECTIONS

• The Complete Black Mask Cases of Oscar Sail (2021) | Buy this book
  Includes all three stories.

FURTHER INVESTIGATION

• The Pulp Paper Master Fiction Plot
  Lester Dent’s sure-fire recipe for writing a successful pulp story.
• Lester Dent’s Rogues Gallery
  An ever-growing list of his detective characters.

Respectfully submitted by Kevin Burton Smith.