Repeat offenders on the street – the system is broken
By Dorothy Dobbie
Small shop owners feel helpless against thieves. For that matter, so do large ones who can afford to hire security.
Grab-and-run thieves are becoming more daring. They don’t really care if there is a security guard on duty or not, because they know that these employees have no real power, that they could be charged with assault if they physically attempt to stop a thief and the court judges the force to be unreasonable. The bar is set very low.
A security guard has no greater powers than any ordinary citizen under the law. Yes, they can make a citizen’s arrest. So big deal. The thief runs away and to stop him you have to use physical restraint measures. He struggles, things heat up, the security guard ends up being charged while the thief just adds another charge to his long list of offences.
It is a minor inconvenience, because he is already awaiting trial for the same offence several times over. And, oh yes. He prays the day of reckoning will never come because, under the Jordan principle, the trial must be held no later than 18 months for this type of crime.
What happens if that doesn’t occur? The case is thrown out of court. The perpetrator gets off scott free. And even if it does go to trial, he may get a slap on the wrist with as little as six months in jail or a $2,000 fine!
Seasoned criminals also recruit kids to steal goods that they will sell on what used to be called the black market.
Some of these thieves are remarkably young, and nearly all are under 18, protected by the Youth Criminal Justice Act. Kids as young as 10 or 11 are also recruited, because they can’t be charged at all. Young as these thieves-in-training are, they are well equipped to defend themselves, some of them carrying bear spray, machetes, and airguns.
Retail thieves are just a part of the mess. Violent criminals are also protected by expeditious trial dates although the court is granted six more months to get them to trial before dismissal of their case. This is where it gets dangerous. A whopping 20% of violent offenders were out on “bail” at the time of their new charges. Indeed, up to 80% of all violent offender cases have been previously charged with an offence according to the Manitoba Integrated Violent Offender Apprehension Unit which was created in 2023 to deal with violent offenders.
And police know that bail breakers are often ignoring their bail conditions. Last March, they announced that, over a two-month span, their bail compliance unit had tracked down or submitted warrants for 336 offenders breaking bail conditions.
It is not just a Manitoba problem. A former Vancouver mayor said that in a single year, 6,300 incidents were committed by the same 40 individuals.
So how do we deal with this? Hiring more police does not help if the perpetrators are out within 24 hours, and often “bail” is no more than a promise to show up for trial.
Worse is the fact that so many never get to trial because of a lack of judges and clerks to hear the case. Right now, the Federal court has five judge vacancies in Manitoba. The Federal government appoints these judges, but it appears Mr Carney is too busy gallivanting around the world to be bothered with such a paltry detail.
In Manitoba, our provincial court system has 43 judges, up only 2 since 2,000, although our population has grown by over 350,000 in that time. There seems to be no public record of the number of judicial vacancies, but clerical positions are the big issue. There are 14 out of the usual complement of 49 – more than 28% – of clerical positions unfilled.
It is hard to find replacements for those clerks who are retiring, and the job can be stressful while also being on the lower end of the wage scale. The rate in Manitoba is $18.90 per hour; you can’t hire a dog walker for that these days.
Skills requirements are also changing as clerks’ roles shift from manual data entry to digital data management, as the role evolves into more of an administrative assistant position.
As we can see, the problem is complex and it is about to get even worse as the province cuts circuit judges – those are the judges who travel to small and remote communities to hear cases. Chief Judge Ryan Rolston announced that 68 annual circuit court sittings will be cut, effective April 1, 2027.
Sittings across the province will be reduced to 108 per year, down from 176.
Instead, they have rechannelled resources into hiring more police officers, ankle monitors, and correctional facilities, although correctional facilities have not increased since 2016, but neither has the prison population – up very slightly from 2,555 in 2016 to 2,582 in 2026.
And guess what? Over, 70% of these people are in jail on remand because they are deemed too dangerous to be allowed out on bail, waiting for trial.
This system needs some serious thought and a plan to cover all the shortfalls if we want to live in a safe community.
Repeat offenders
By Shauna Dobbie
When I was a kid, I thought that if you stole something and got caught, you went to jail. Simple as that. Wasn’t that the whole point of jail?
I have since learned there is a great deal more involved. First, you have to get caught, then you have to be charged, then – after months of waiting, not in jail – you might get sentenced to a fine or community service or maybe a bit of time in prison.
In Junior High in the 1980s, my Social Studies teacher said that theft under $200 was a relatively minor offence, roughly the sort of crime Americans would call a misdemeanor. Today, the dividing line is $5,000.
Two hundred to five thousand. The cost of everything has gone up, but not by 25 times.
The law does not literally declare every theft below that line minor. Theft under $5,000 can still be prosecuted by indictment and can carry a prison sentence, though the maximum sentence for it is two years. But categories send messages. Calling the theft of $4,999 “theft under $5,000” places it, at least in the public imagination, alongside a teenager pocketing a lipstick.
If I were a shopkeeper, I could understand the system treating a $150 theft as a relatively small matter, though a few of those every week would have me fuming. A $5,000 theft would leave me questioning my life choices. When I worked in retail in Toronto fifteen years ago, $5,000 in gross sales was a pretty good day for the entire mid-sized store.
The threshold tells retailers, police, courts and offenders which losses the system considers most serious. Five thousand dollars is a remarkably large amount to place on the less-serious side of that line. The problem is not that the law treats one $150 theft as a minor offence. The problem is that it can treat the fifteenth $150 theft as though the first fourteen never happened.
Shoplifting is rising sharply across Canada. Police reported 208,941 incidents in 2025, up 11 percent from the year before, the fifth straight annual increase, and up 79 percent since 2015. Those are only the thefts that got reported. I expect some portion of that is people stealing food or other necessities, understandable if not excusable. But there is also a smaller, more persistent group who do this again and again, sometimes stealing goods specifically to resell.
Winnipeg police call these people prolific offenders, which is a remarkably polite way to put it.
In December 2025, Winnipeg police wrapped up a month-long retail theft crackdown with 72 arrests, 25 of them held in custody. Seven of those arrested were on Crime Stoppers’ list of the 10 most wanted retail thieves. Officers laid more than 196 charges and recovered nearly $24,000 in stolen property.
This is not a hungry single mother stealing a loaf of bread, nor the teenager who pockets a lipstick once and gets caught. These are people who have figured out that retail theft can be repeated, more or less indefinitely, because the resistance to it has largely disappeared.
Retail employees are, quite rightly, told not to engage shoplifters. A package of steaks is not worth a cashier getting stabbed. Thieves know this too. They can fill a bag, walk toward the door and be reasonably confident that the 19-year-old at the register has been specifically instructed not to tackle them.
That safety policy makes sense. What does not make sense is removing the resistance at the point of sale and failing to replace it anywhere else – and I do not mean by making everyone show identification on the way into the store (ahem, Manitoba Liquor Marts). I mean rapid police follow-up and consequences that escalate for people who keep doing it.
Suppose police do catch our thief. For a relatively minor, nonviolent offence, the accused will often be released with conditions and a date to appear in court. Release is not automatic, however. Police and courts may consider whether the person is likely to continue offending, breach conditions or fail to appear.
The problem arises when the system sees each theft separately. Our thief may collect new charges and new release conditions while the earlier cases move through court. Unless police connect the reported incidents quickly, many of them will never become part of the case against that offender. Even when charges are laid, separate files may proceed on different schedules and obscure the scale of the pattern.
I don’t think the answer is simply locking everyone up. Research on imprisonment is discouraging if the goal is reducing reoffending. A Canadian meta-analysis covering 336,052 offenders found no evidence that prison sentences reduced recidivism. Longer imprisonment was associated with a slight increase, not a decrease, in reoffending.
Prison does incapacitate someone temporarily. Put a prolific thief away for six months and he cannot steal from the grocery store during those six months. That does not mean the sentence will change what happens in month seven, when he is released; in fact, he’s been released after six months of chat time with other criminals, learning to perfect the craft.
The solution resides with retailers, police and the justice system. Retailers should record every incident in a standardized system; they should upload video, descriptions and the value of the goods within 24 hours. Stores in the area can then know what products, locations and hours produce the greatest losses and protect them with tags, controlled displays, staffed checkouts or targeted security.
Winnipeg is not starting from nothing. WPS accepts online retail-theft reports, reviews them within 48 hours and places approved reports in its records system. Its Property Crime Unit has used those reports and store video to connect thefts committed at different businesses by the same person.
WPS also runs targeted enforcement projects. An East District initiative involving community-support, property-crime and rapid-response officers made 149 arrests and recovered $24,000 in merchandise between late May and August 2026.
What WPS does not publicly promise is immediate investigation of every reported theft or automatic comparison of every report across every retailer. Its strongest results appear when investigators have already identified a pattern or when officers are assigned to a temporary enforcement project.
That approach should become routine. WPS needs permanent retail-theft capacity within its Property Crime Unit, with investigators responsible for connecting reports from different stores. One $150 theft may not justify a major investigation. Fifteen thefts by the same identifiable person should be treated as a pattern, not as fifteen unrelated minor files.
The response should then escalate. A first-time, nonviolent offender might receive diversion, restitution or community service. Continued theft should bring tighter release conditions, orders to stay away from affected stores, closer supervision and, when necessary, custody. Prolific-offender cases should receive coordinated court management so that charges do not accumulate faster than the courts can address them.
Police must also investigate the people and businesses buying the stolen goods. Repeated theft becomes profitable only when merchandise can be converted into cash.
The solution will cost money, and that cost should be divided sensibly. Retailers should pay for effective store controls and usable evidence. Government should pay for investigation, prosecution and courts. Catching criminals is a public responsibility, not a cashier’s second job.
The strongest deterrent is the reasonable expectation of being identified and caught. Make detection, charging and case resolution swift enough that stealing fifteen times no longer feels like getting away with 15 minor offences.