By admin 
A San Luis Obispo County man who has faced over 50 criminal charges and nearly half as many mental health competency cases in recent years was arrested several times within months of being released from jail.
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After being freed in May, Gabriel David Canaday, 48, is currently back in custody at San Luis Obispo County Jail facing multiple first-degree burglary charges as well as charges for allegedly entering an operational area at a local airport unauthorized, skipping the bill at two Paso Robles hotel and restaurant businesses, drug possession, DUI, trespassing, loitering on private property and giving false identification to a law enforcement officer, according to court and jail records.
He faces the 10 charges — including two felonies — across seven cases filed since June, court records show. In every case but one, filed Monday, his defense counsel declared doubt as to his mental competency to stand trial.
His bail was set at $56,000, according to the Sheriff’s Office Who’s In Custody database.
Before his current charges, he had been serving an 120-day sentence in jail for trespassing, driving with a suspended license, second-degree burglary — entering someone’s detached garage — and a DUI, court records show.
He was remanded to custody on April 29 but was released on probation before he completed his sentence, court records show. His most recent arrests are also in violation of his probation.
Canaday has a long criminal record dating back to 2019, when he was involved in a feud with the founder of Tobin James Cellars, Tobin James Shumrick, who shot at Canaday’s golf cart with a shotgun in early 2020 when Canaday was allegedly harassing employees in the parking lot of the winery.
Canaday lived across the street from the Paso Robles winemaker at the time. Shumrick claimed he shot at Canaday’s vehicle in self-defense after months of alleged harassment and trespassing from Canaday onto the Tobin James Cellars property.
By then, Canaday already faced numerous charges for violating court protective or stay away orders, including at least one temporary restraining order filed by Shumrick in October 2019, court records show. Shumrick’s felony charges were eventually reduced and he accepted a plea deal for misdemeanor vandalism.
In total, Canaday has been booked into the jail 25 times since 2010 including his current incarceration, Sheriff’s Office spokesperson Tony Cipolla told The Tribune.
For 16 of those arrests, he stayed in jail for just a day or two before making bail or being released after a citation, but the other nine stays have been for longer periods of time.
He has faced over 50 criminal charges, most of them misdemeanors, court records show. At least 20 were violations of court protective or stay away orders that were eventually dismissed.
Mental health competency cases were opened on 21 of the 23 criminal cases he has faced in court since 2019, indicating that doubt was declared as to his ability to stand trial due to his mental health, court records show.
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Why was repeat offender arrested again?
In his most recent string of arrests, Canaday was first arrested after he allegedly left the Paso Robles Inn without paying for his meal or room on June 15, according to the complaint.
The Paso Robles Inn directed The Tribune to its owner, Martin Resorts, for comment, but the corporation did not respond.
About a month later, on July 17, Canaday was arrested at the Paso Robles airport on suspicion of entering an operational area without authorization, according to the complaint. He was also charged with possession of methamphetamine.
The U.S. Transportation Security Administration issued an alert on Canaday to local airfields, including the Oxnard Airport, after the alleged incident that said he had ”repeatedly shown up at airports and attempted access to airfields through vehicle gates, keypads or by visiting (Fixed-Base Operators)” — which are private airport areas — and that he had “used the name John Jacob and, in the past, has inquired about flights going to Europe,” Ventura County’s deputy director of airports Casey Pullman, told The Tribune.
A few days later on July 20, Canaday allegedly gave false information to a police officer, attempting to identify himself as someone else so as to evade arrest, according to the complaint.
On July 25, he was again arrested for trespassing and prowling or loitering on private property, according to the complaint.
The next day, he allegedly tried to leave the Blast and Brew bar and restaurant in Paso Robles without paying his bill, a manager at the restaurant told The Tribune.
He was released soon after each other these arrests, but on Aug. 9, he was arrested while allegedly trying to break into a home and trailer on Mill Street in San Luis Obispo, according to court records.
Canaday has remained in jail custody since.
Now that doubt has been declared as to his mental competency, he will undergo a psychiatric evaluation to determine his ability to understand the court proceedings and charges against him.
If deemed incompetent to stand trial, he could either remain in jail until his competency is restored or he could potentially qualify for mental health diversion court, which could route him out of the jail and into a community-based treatment program.
Canaday’s next court appearance for all his cases is scheduled for Sept. 10 for the receipt of doctor’s reports.
This story was originally published August 19, 2026 at 10:00 AM with the headline “Man who feuded with SLO County winemaker is back in jail on long list of new charges.”
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