1584 Thomas Leary

 Thomas Lewis (1855-19??, aka Thomas Leary, Kid Leary). American sneak thief and bank robber.
After a first arrest in 1874, Lewis was arrested again in 1877 by New York detectives for the robbery of the Cambridge National Bank of Cambridge, Massachusetts. However, no evidence was found, and he was released.
A month later, Lewis was arrested for stealing a trunk with $10,000 worth of jewelry from a salesman by arranging for the trunk to be diverted at a railroad depot. Lewis was convicted of this crime and sent to Sing Sing for a term of five years.
In October 1881 he robbed the Baltimore bank.
In 1893 he was arrested for concealing a kit of burglar’s tools–possession of which was a felony. He was sentenced to another five years at Sing Sing.
Perhaps seeking different luck, Lewis went west. He was arrested in Waukesha, Wisconsin in 1903, for his involvement in the robbery of the Eagle Bank. Upon walking out of prison, Lewis migrated to Chicago and he was never heard from again.

- "Dark red hair. Eyes, bluish gray. Complexion, light."  https://criminalsrevised.org/thomas-lewis-6/

 

1581) Gilbert James Fitzgerald

Gilbert J. Fitzgerald (aka James Fitzgerald, The Kid, Red Fitz, 1856-1933). American banco steerer.
 He was born to Irish immigrants who had settled in Milwaukee.
In 1881 he formed a gang with Billy Harris and Johnny Norton, and headed to New Orleans.
The following year the gang headed north to Boston, where they happened upon the most prominent bunco victim in history: Charles Francis Adams–son of John Quincy Adams and grandson of John Adams; and himself a former Ambassador to Great Britain. Fitzgerald was found guilty and sentenced to five years in the Massachusetts State Prison.
In 1915, Fitzgerald was arrested for being one of the operators of an elaborate “wireless wiretap” betting parlor con, first developed by Larry Summerfield and Timothy Oakes. Fitzgerald’s partners in this venture were Charles and Fred Gondorf; and Fitzgerald was sometimes introduced to others as “Harry Gondorf.” If the name sounds familiar, it is because that was the character name of the wireless wiretap operator (Paul Newman) in the movie The Sting: Henry Gondorff.
Fitzgerald was free by 1917. Over the next several years, he took several trips to Havana, which was then a resort for wealthy Americans.

-  “Red hair, dark auburn eyes, sandy complexion, straight nose, beard red (when worn), hair very thick and coarse... He was known among his friends and acquaintances as ‘Reddy,’ a name applied to him perhaps on account of his fiery red hair." https://criminalsrevised.org/113-james-fitzgerald/

 

1579) Charles Hylebert

Charles Hylebert (born John William Heil, aka Cincinnati Red, aka Red Hyle, 1850 - 1904). American hotel thief.
He was born and raised in Cincinnati, where he learned the butcher's trade. He started his career as a thief when he was twenty and soon began one of the most celebrated hotel thieves in the US.
In 1880 he was arrested and sentenced to the Georgia penitentiary for a hotel robbery in Atlanta. In 1885 he was sentenced to four years in the Northern State prison at Michigan City.
Red escaped conviction during the years between 1889 and 1904, though he was arrested and tried many times: in Chicago, Washington, Baltimore, Louisville, and New York.
In November 1904, Heil was found unconscious in a rooming house in Chicago. The stove in his room was leaking gas. The coroner declared that he died from accidental asphyxiation.

  
- "He was called Red Hyle on account of his red hair and florid face." https://books.google.it

 

1078) Al Jennings

Alphonso J. "Al" Jennings (1863 – 1961). Attorney in Oklahoma Territory who at one time robbed trains. He later became a silent film star and made many appearances in films as an actor and technical adviser.
In 1913 he wrote Beating Back, a novel loosely based on his outlaw life. This novel portrayed the law as persecutors of the innocent and Jennings as an honorable lawbreaker who possessed immense skills in horsemanship and marksmanship. To coincide with this novel, The Saturday Evening Post wrote a series of interviews with Jennings that perpetuated the same messages as his novel. He re-created one of his bank robberies in the 1908 film The Bank Robbery.
Jennings moved to Oklahoma City in 1911 and became active in politics. In 1912 he won the Democratic nomination for Oklahoma County attorney, but he lost the general election.
Retiring from law and politics, Jennings moved to California and worked in the motion picture industry making Westerns. A film biography of him was made in 1951, Al Jennings of Oklahoma, with Dan Duryea in the title role.

- "Although some of the gang wanted to surrender, Mrs. Harless said the short bandit with the red hair - that was Al - said he'd rather die first."  https://www.coopertoons.com/caricatures/aljennings_bio.html

- "He had a head of fiery red hair and a dynamic way of speaking."  https://books.google.it/books…

- "Al Jennings’s distinctive red hair made him easily recognizable even when masked, and he was captured in 1897."  http://fayllar.org/clara-bow-in-mantrap-victor-fleming-1926…

928) Bill Doolin

William "Bill" Doolin (1858 – 1896). American bandit outlaw and founder of the Wild Bunch, a gang that specialized in robbing banks, trains, and stagecoaches in Arkansas, Oklahoma, and Kansas during the 1890s.

- "At six feet two inches tall and a mere 150 pounds, outlaw Bill Doolin was a stringbean cowboy with auburn hair, blue eyes and reportedly wore a “ragged brindled” mustache."  https://truewestmagazine.com/kill-bill/

- "The son of a Johnson County, Arkansas, farmer, Doolin was six feet, two inches tall, weighted 150 pounds, had auburn hair, blue eyes, a hooked nose and wore a ragged mustache."  https://www.nps.gov/fo…/learn/historyculture/bill-doolin.htm

- "Here Emmett became the saddle companion of slender, six-foot-two, auburn-haired, drooping-moustached, gander-blue-eyed Bill Doolin."  https://books.google.it/books…

916) George Waightman

George "Red Buck" Waightman (1850 - 1895). American Old West outlaw, and member of the Doolin-Dalton gang. His surname was also spelled Weightman.
Waightman was born in Tennessee, 1850. He is known to have been a cowboy prior to meeting Bill Doolin and Bill Dalton in 1892. He joined their gang shortly thereafter, taking part in numerous bank robberies and train robberies over the next three years. By 1894, however, US Marshals were hot on the gangs trail, and several members had been captured or killed. The gang split up to make things more difficult for the Marshals. Waightman was eventually tracked down, on October 2, by Deputy US Marshal Chris Madsen, and in the ensuing shootout Waightman was killed.

- "Trouble in a well muscled package topped by dark red hair (the origins of his nickname, "Red Buck")..."  http://homebrewedmojo.blogspot.com/…/the-death-of-red-buck-…

- "Red Buck, named for his mop of red hair..."  https://books.google.it/books…

- "His hair was red, which gave him his nickname."  https://www.wikitree.com/wiki/Armstrong-273

915) Big Harpe and Little Harpe

Micajah "Big" Harpe, born Joshua Harper (before 1768 – 1799), and Wiley "Little" Harpe, born William Harper (before 1770 – 1804). Murderers, highwaymen, and river pirates who operated in Tennessee, Kentucky, Illinois, and Mississippi. They are often considered the earliest documented serial killers in the United States, reckoned from the colonial era forward.
Loyal to the British Crown during the American Revolution, the Harpes became outlaws after the war and began robbing and killing settlers in the remote frontier west of the Appalachian Mountains. They are believed to have killed thirty-nine people, and possibly as many as fifty. As the Harpes' crimes gained notoriety, vigilante groups formed to avenge their victims, and they were eventually tracked down and executed around the turn of the century. Their legendary savagery has since entered American folklore, appearing to have been motivated more by blood lust than financial gain.
Though many historical accounts identify them as brothers, it is also possible they were actually first cousins named Joshua and William Harper who emigrated from Scotland in 1759 or 1760.
Their hair colour is disputed. According to the description given by Kentucky Governor James Garrard, they both had black hair, while other sources describe one or the other as red-haired.


Big Harpe:

- "He was described as typically being "diry and shabby," the darkness of the grime offset by a thatch of "fiery red hair."  https://www.findadeathforum.com/showthread.php…

- "He wore no covering on his head, so the natural protection of thick, coarse hair, of a fiery red, uncombed and matted, gave evidence of the rudest exposure."  http://hendersonkyhistory.com/HarpeBros.htm

Little Harpe:

- "His description of Little Harpe was similar, except he had red hair and "bore a look of cunning and treachery."  http://www.thepastwhispers.com/ALHN_Harpes.html

- "Big Micajah, described as bony and muscular, was the brawn to the brains of red-haired Wiley..."  https://www.scotsman.com/…/the-harpe-brothers-scots-who-bec…

- "Wiley, or Little Harpe, was at times described as having black hair, but in fact he seems to have been red-headed."  http://helenroulston.com/whoweretheharpes.html
 
- "Red hair was the particular mark of Little Harpe."  https://books.google.it/books…

- "Little Harpe was small and wiry, with fox-red hair."  https://books.google.it/books…

- "Wiley had flaming red hair, was sllightly smaller in stature and went by Little Harpe."  https://books.google.it/books…

880) John "Red" Leary

ohn "Red" Leary (1837 - 1877). Irish-born member of the American gang of bank robbers formed by George Leonidas Leslie (1842–1878), known as the Leslie Gang.

Husband of Catherine "Kate" Brennan. 

- "He was a typical desperado in appearance, with his shock of red hair and his bristling red mustache..."  https://books.google.it/books…

- "Leary was over six feet tall, with bright red hair and mustache..."  https://books.google.it/books…

- "Red Leary was nicknamed as such not only because of his fiery red hair and beard, but also because of his violent temper."  https://books.google.it/books…

827) Édouard Carouy

Édouard Carouy (1883 - 1913). French anarchist. 
In 1911 hejoined a gang led by Jules Bonnot. Amongst comrades they were known as 'illegalists', which signified more than the simple fact that they carried out illegal acts. Illegal activity has always been part of the anarchist tradition, especially in France.
On 25th March, 1912, the gang stole a De Dion-Bouton car in the Sénart Forest by killing the driver. Later that day they killed two cashiers during an attack on the Société Générale Bank in Chantilly. Leading anarchists in the city were arrested and Edouard Carouy was betrayed by the family hiding him. 
He was sentenced to hard labour for life and committed suicide in prison with poison.

Another red-haired member of the Bonnot gang was René Valet.  

- "Édouard Carouy had meanwhile dyed his hair from red to black..."  https://books.google.it/books…

825) René Valet

René Valet (1890 - 1912). French anarchist.
In 1911 Valet joined a gang led by Jules Bonnot. Amongst comrades they were known as 'illegalists', which signified more than the simple fact that they carried out illegal acts. Illegal activity has always been part of the anarchist tradition, especially in France.
On 24th April, 1912, three policemen surprised Jules Bonnot in the apartment of a man known to buy stolen goods. It is claimed the building was surrounded by 500 armed police officers, soldiers and firemen. Bonnot was able to wound three officers before the house before the police used dynamite to demolish the front of the building. In the battle that followed Bonnot was shot ten times. He was moved to the Hotel-Dieu de Paris before dying the following morning.
Valet remained on the run with Octave Garnier until 15th May, 1912. According to Victor Serge: "Octave Garnier and René Valet, caught up at Nogent-sur-Marne in a villa where they were hiding out with their women, underwent an even longer siege, taking on the civil police, the gendarmerie, and the Zouaves. They fired hundreds of bullets, viewing their attackers as murderers (and themselves as victims) and, when the house was dynamited, blew out their own brains."
Another red-haired member of the Bonnot gang was Édouard Carouy.

- "I remember his fine, square-set ginger head, his powerful chin, his green eyes, his strong hands, his athlete's bearing..."  https://spartacus-educational.com/ANA-Rene_Valet.htm

- "... others joined the first few such as red-haired Rene Valet..." https://spartacus-educational.com/ANA-Stephen_Monier.htm

- "... Victor's red-headed Left Bank soul-brother René Valet, aka Carrot Top..."  https://books.google.it/books…

- "The next day, the redhead, whose name was Valet..."  https://maisondetraductionblog.wordpress.com/…/updated-11-…/

298) Jesse James

Jesse Woodson James (1847 – 1882). American outlaw, bank and train robber and leader of the James–Younger Gang. Raised in the "Little Dixie" area of western Missouri, James and his family maintained strong Southern sympathies. He and his brother Frank James joined pro-Confederate guerrillas known as "bushwhackers" operating in Missouri and Kansas during the American Civil War. As followers of William Quantrill and "Bloody Bill" Anderson, they were accused of participating in atrocities against Union soldiers and civilian abolitionists, including the Centralia Massacre in 1864.

- “The fact that Jesse James suffered from ophthalmic conjunctivitis is in sync with J. Frank Dalton having died a blind man. But the man who Ford killed in 1882 did not suffer from ophthalmic conjunctivitis. Neither did he have red hair like Jesse. The man who Ford killed had black hair.” http://virtualcities.com/ons/tx/y/as/txy60a23.htm

- “The man who was killed and buried in Missouri did not have the eye problem, and according to the doctor, also had black hair. Jesse James had red hair." http://www.durangotexas.com/eyesontexas/…/granbury/james.htm

20) John Herbert Dillinger

John Herbert Dillinger (1903 – 1934). American gangster in the Depression-era United States.

- "Dillinger had taken great precautions to prevent his being recognized. His face had been lifted by a surgical process since his last picture was taken and he had dyed his hair a darker shade than its natural light reddish brown." https://archive.nytimes.com/www.nytimes.com/learning/general/onthisday/big/0722.html

- "Former Indiana farm boy stood five feet nine inches, weighed 168 pounds and had wavy brownish-red hair and a dimpled chin".   https://books.google.it

17) John "Red" Hamilton

John "Red" Hamilton (1899 – 1934). Canadian criminal and bank robber active in the early 20th century, most notably as an associate of John Dillinger.

- "John Hamilton was known as "Red" because of his dark red hair." https://www.awesomestories.com/asset/view/Red-Hamilton-Escaped-Michigan-City-Prison