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The criminal career of Gilbert Lare, aka “The Del-Mar-Va Bandit,” began with a seemingly minor affair.

Wilmington News Journal, Dec. 27, 1926: Gilbert Lare, a young man of [Federalsburg, Md.], was arrested by Constable Thomas Nichols [and charged with] breaking into [Leon Todd’s] store on South Main Street Wednesday night and removing two slot machines. … The machines were found early the following morning along the river shores, broken up, and nearly $40 in quarters and nickels removed from them.

There is not much in this incident that hints at the daring and brazen escapades that would soon follow. Still, I can’t help but wonder if either Lare or Constable Nichols had a clue during the chase leading up to this arrest that their cops-and-robbers relationship would continue through most of the next decade.

From the same article: When the arrest was made Lare was some distance out of Federalsburg, walking toward Bridgeville. On being hailed by Constable Nichols, who caught up to him in a car, [Lare] at once took to flight and ran through Tanyard Branch, a stream of water crossing the road. After a short pursuit up the bed of the branch, he was overtaken and subdued.

The Earliest of the Houdini Escapes

Constable Nichols locked Lare up in the Federalsburg jail. Lare escaped. He was captured in Seaford, Del. and put in jail there. He escaped again. The following summer, the 20-year-old was back in jail after getting nabbed while trying to sell typewriters he had stolen from Wicomico High School. Lare had a thing for office supplies.

Salisbury Daily Times, Aug. 19, 1927: Gilbert Lare, who escaped from jails at Seaford, Del. and Federalsburg, Md., made an unsuccessful attempt to saw his way from the Wicomico County jail yesterday. Lare had sawed one of the iron bars in the south window at both ends and could have removed it with little effort in a few minutes. After darkness, he could [have crawled] out through the window and gained his freedom. A small saw about one-and-a-half inches in length and a knife with knocked blades used to sever the bar were found in the cell by the sheriff.

Lare reached a deal with prosecutors, admitting only to “receiving stolen goods” but not pleading guilty to the burglary and larceny charges also on his docket. I did not find any story about the final sentence, but he was back at the work of his young life soon enough. He was arrested in Wilmington on July 3, 1928 while trying to unload tools and supplies he had pilfered from a school in Delmar, Md. Delaware authorities turned Ware over to their colleagues in Maryland, but Ware promptly escaped from the jail on the Maryland side of Delmar.

If you are keeping score, that is three jailbreaks in a year and a half for a young man barely out of his teens.

In Salisbury, a Rope Made of Blankets

In December 1928, Lare found himself on the second floor of the jail in Salisbury, Md. after being arrested for stealing typewriters from Wicomico High School.

West Main Street in Federalsburg–a couple of decades before the glory days of Gilbert Lare.

Salisbury Daily Times, Dec. 12, 1928: Hacksaws, blanket ropes, and sawed steel bars figured prominently in a spectacular … jailbreak early this morning when Gilbert Lare, [21], and Dalton Smith, 17, escaped from the southwest cell of the Wicomico County prison. … Lare, whose uncanny faculties for escaping from Eastern Shore jails has made him an apt student of the magical influence of the late Houdini, is believed to have engineered and executed the escape.

The pair got used a saw to cut through the bars on a window, creating an opening just wide enough for a man’s shoulders. Their work was discovered only when city police officers outside the building noticed a trail of blankets tied into a makeshift rope hanging from the second of the jail.

Dalton Smith was captured a few days later. He would be sentenced to a couple of years in reform school. But Lare proved a bigger challenge, even with his old nemesis Constable Nichols on the case.

Wilmington News Journal, Dec. 17, 1928: “Constable Thomas L. Nichols [of Federalsburg], remembering Lare’s penchant for coming to his former home after his escapes, watched for him [with the help of] two state troopers, but not until night did they get on the fugitive’s trail. Hearing that he was in a colored barbershop …  north of [town], the officers hurried there, but as they entered the front door Lare slipped out the rear and sprinted into the woods, and since then has not been seen.”

The Del-Mar-Va Bandit Turns Downright Playful

Here is where the story of Gilbert Lare takes a turn worthy of a Hollywood movie about a charismatic antihero who positively taunts the police officers on his trail.

Wilmington News Journal, Jan. 4, 1929: Roy Drew, a citizen of Federalsburg, received a souvenir postcard [from the Delmarva jail-breaker] Gilbert Lare a day or so ago, postmarked Daytona, Florida and on which Lare had written: “Tell Constable Thomas Nichols that if he had looked closer he would have caught me.”

Though never confirmed, police developed a theory that Lare had skedaddled in the company of another legendary Delmarva criminal, Alfred Brittingham, whose specialty was stealing cars.

Wilmington News Journal, Jan. 5, 1929: “No cars have been reported stolen, no holdups perpetrated and all tips as to Brittingham’s whereabouts have proven baseless. [Brittingham] had been traveling through the peninsula, picking up a new car [whenever] the one he was driving ran out of gas. Abandoned and undamaged cars blazed his trail through Somerset, Wicomico, and Worcester counties.”

That postcard was not the only missive Lare sent while on the lam. Lare also sent a playful Christmas card directly to Constable Nichols. In it, he promised to return to town soon: “Watch out for me,” it said.

A railroad repair crew works near Federalsburg in the mid-1930s.

The Evening Journal, Jan. 17, 1929: The looting of the fertilizer warehouse office of Herman Wright [in Federalsburg] and the theft of a large truck is taken by local officers as mute evidence of the return of Gilbert Lare, the Peninsula’s champion jailbreaker to his home, just as he promised on a Christmas card to a local officer. The man who is credited with saying that he has broken out of every jail on the Peninsula has been as large since his break from the Salisbury jail several weeks ago.

Lare had stolen that truck from a fertilizer company, then driven it to Herman Wright’s office and backed it up to a loading dock where he loaded all of the office furniture in the joint—chairs, adding machines, typewriters, and more.

From the same article: “An office stripped of all furnishings with the exception of a heavy safe and the swinging doors of a warehouse stood as testimonials today of the daring of a man of whom residents along the Eastern Shore speak respectfully for his many accomplishments.

There are two funny extras worth noting about this escapade. First, Lare had already committed this exact same crime. The goods stolen on the first heist were eventually discovered and returned. Here he was stealing the same items again. The office had hired a night watchman, but he wasn’t on duty the night of the second heist.

Also, just before pulling off this repeat heist, Lare had engaged in conversation with some “colored men” gathered along the railroad tracks that ran through Federalsburg. He pointed to lights on in a distant office and told those men: “I see Herman Wright and R.O. Dean have got their lights on—[they] must be scared somebody will break in and steal.” Then he added, “The next time I leave Federalsburg I’ll take half the town with me.'”

Busted by Way of a Vigilant Farmer

The next day, Jan. 18, the headline in the Evening Journal read: “Outlaw Caught in Kent, Co., Md.”

From the article: His capture was affected by the suspicion of H.W. McMahon, [a Kent County farmer] … who recognized the truck of G.T. Bell and Son [when it] stopped at McMahon’s place, near Chestertown. After [Lare] drove away, McMahon called the sheriff of Kent County, Md., and officers were sent in pursuit.”

The stolen goods were still inside when the police pulled that truck over. Gilbert Lare was soon back in jail, this time in Denton.

From the same article: “By a number of people [in Federalsburg] who have known the boy since his childhood it is thought that he cannot help committing the acts, and that possibly an operation on the brain might correct his apparently unconquerable mania for breaking in and stealing.”

Wilmington News Journal, Jan. 22, 1929: “The sentiment is growing that Lare should be given a mental examination at some institution by experts to ascertain if pressure on the brain or some other ailment is the cause of his criminal tendencies. It is pointed out that after breaking into a place he makes no effort to cover up his tracks, and in a short time will appear in that town, on the streets.”

Even Houdini Can’t Escape from the Denton Jail

By this point, you know that Gilbert Lare tried his very best.

Gilbert Lare was unable to escape from the Caroline County Detention Center in Denton, Md.

Wilmington News Journal, Jan. 22, 1929: “Lare was foiled Sunday night in an attempt to escape from the Denton jail. [He] has taken up the floor of his cell and was about to get away by a drainpipe when he was frustrated by the alertness of Sheriff Jackson. The youthful offender was then placed in a specially constructed steel cage [that is usually reserved for murderers.] It is believed [this cell] will hold him.”

Guess who came to visit Gilbert Lare in the Denton jail? His old friend and nemesis from the Federalsburg police force.

Wilmington News Journal, Feb. 8, 1929: [When] visited by Constable Thomas L. Nichols of Federalsburg yesterday, [Lare] said: “I wish they’d hurry up and try me and send me where I’m going. I am making no headway at all in this place!”

In early March, rumors spread like wildfire through Delmarva that Gilbert Lare had escaped again. Caroline County Sheriff Jackson felt obliged to give interviews to reporters so as to assure the public that The Del-Mar-Va Bandit was still inside that cage reserved for murderers, though not for lack of trying.

Wilmington News Journal, March 6, 1929: “In the last few days the Del-Mar-Va bandit removed several long, flat pieces of iron on which run the wheels of the sliding doors of the special steel cage in which he is held, and hid them in his bed, but they were discovered.

A Stay in the Maryland Penitentiary

Wilmington News Journal, April 8, 1929: Gilbert “Dicky” Lare, 22-year-old Federalsburg youth … who has achieved the title of the “Del-Mar-Va” Bandit” in the past four years, was sentenced to two years in the Maryland Penitentiary.”

After Lare served that sentence, things stayed quiet for several years. Lare returned to the Federalsburg area. He took on real jobs as a carpenter. But in the end, he wasn’t quite ready to give up on his life of crime.

Wilmington News Journal, Nov. 6, 1934: Gilbert “Dickie” Lare of Federalsburg who three or four years ago made a reputation in a large area of the Peninsula as a result of his implication in robberies and jailbreaks … is suspected of having been the “brains” of a series of recent robberies. Lare was arrested yesterday after William Edwards, a Norfolk Negro, is alleged to have confessed his part in the robbery of Covey & Williams hardware store.

Later in the same article: [Lare] engineered the robbery and gained entrance to the hardware store by placing a ladder against a high window. Edwards was captured after Constable Nichols and Officer Floyd Phillips chased him through cornfields. Two Negroes [also] alleged to have been involved are still at large.”

The next year brought more of the same.

Wilmington News Journal, Oct. 7, 1935: Gilbert Lare, a Federalsburg youth, is charged with having broken into and robbed the storehouse of Jacob O. Williams, hardware and automobile dealer.

And the year after that, more of the same.

Wilmington News Journal, Dec. 1, 1936: Committed to the local lock-up when arrested for questioning in the recent triple store robbery [in Federalsburg], Gilbert “Dickie” Lare, sometimes called champion jailbreaker of the Eastern Shore… proved true to form in attempting to break his bonds, although his attempt was foiled by police. … Removing some of the jail’s plumbing pipes to use as tools, he managed to break and remove several cement blocks from the building as a means of exit when his work was detected just in time.

As an old newspaperman myself, I have to give props here to the anonymous writer of this article who, in recounting Lare’s long history of escapes, employs Gilbert Lare’s nickname in describing him as “the slippery Dickie.” Lare was soon back behind bars in Denton, the one jail he couldn’t seem to escape from.

The Bandit’s Trail Ends … Or Does it?

Presumably, Lare was sent back to the penitentiary for a while, though I have not come across confirmation of that in old newspapers. The trail of the Del-Mar-Va bandit runs pretty cold after this, though there is a possibility that Lare eventually settled in Salisbury, began working again as a carpenter, and lived a mostly crime-free life. Fifteen years after that last arrest above, this intriguing little item popped up in the Salisbury paper.

Salisbury Daily Times, April 5, 1951: [A Salisbury man was] jailed by City Police yesterday on breach of trust charges. Gilbert Lare, 46, of Camden Ave. and Market St., is being held in lieu of $1,000 bond. He is charged by Harold L. Porter, 1302 Russel Ave., an appliance dealer, with a breach of trust totaling $65.

The age is about right, but I do not know one way or the other if this was the same Gilbert Lare. Nor do I know for sure if an obituary that appeared in the Salisbury Daily Times on Nov. 24, 1976 is about the same Gilbert Lare. The obituary describes a man at 72 years old—that’s roughly in the ballpark of the age “The Del-Mar-Va Bandit” would have been. The brief article describes him as a “retired cabinetmaker,” which fits with his earlier forays into carpentry work. But it puts his birthplace at Hurlock, Md. and makes no mention of Federalsburg.

Nor, of course, does it make mention of the exploits “The Del-Mar-Va Bandit.” This Gilbert Lare–again, it may or may not be the same man–had two daughters and three grandchildren. If he was the Bandit, here’s hoping he grew up into an outstanding (and upstanding) family patriarch.

–written and posted by Jim Duffy on June 30, 2020 for Secrets of the Eastern Shore/Whimbrel Creations, LLC. All rights reserved.

FOOTNOTE #1: To avoid any confusion that might be caused by the way the articles quoted here mention a couple of times how  Gilbert Lare hung out in the “colored” section of Federalsburg while hiding from police officers, “The Del-Mar-Va Bandit” was, in fact, a white man.

FOOTNOTE #2: The two photos of Federalsburg included here are in the collection of the Federalsburg Historical Society. The photo of the Caroline County jail is in the Library of Congress collection.

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