More Than One Line Crossed in City Cops Arrest

Michael Dowd - NYPD Photo Array
Michael Dowd (2nd from left) – NYPD Photo Array

It seems more than one line may have been crossed last week in the aftermath of a lengthy investigation that took down a front line member of the Winnipeg Police Service.

On September 16, 2016, Deputy Chief Danny Smyth held a press conference announcing the arrest of Constable Trent Milan (42), an eighteen (18) year veteran of the Service.

Smyth indicated the investigation into Milan’s conduct dated back to 2010 when he was assigned to the Street Crime Unit. The allegations pertain to his handling of property, drugs and cash seized in a number of criminal investigations.

Milan, it seems, is Winnipeg’s mini version of infamous NYPD crooked cop Michael Dowd whose criminal exploits were recently explored in a 2014 Netflix documentary called The Seven Five. (Dowd worked in the 75th precinct in New York City.)

The Seven Five
The Seven Five

When the dust settled, Dowd was convicted of racketeering and conspiracy to distribute narcotics.

He was sentenced to 14 years in prison.

If convicted, Milan could suffer a similar fate.

The Fall From Grace

So how does a member of a Police Force, who takes the sacred oath to serve and protect, fall so far from grace.

It can be complicated.

That’s because human beings are complicated.

Flawed, imperfect, weak…

Trent Milan is not the first WPS Officer to tarnish the badge in this fashion and he won’t be the last.

Milan and others before him fell prey to the lure one or more of the seven deadly sins.  Most often greed, addiction (booze or drugs) or sex are the culprits.

There are no excuses.

These are lines that can never be crossed.

So How Did We Get Here?

While I’ll never truly understand how a Police Officer could sacrifice his career, reputation and ability to support his family, my experience on the inside gives me unique insight into how we got here.

That understanding requires a brief history lesson.

On November 21, 2005 the Winnipeg Police Service officially launched Operation Clean Sweep, a task force consisting of uniform police officers mandated to combat street-level violence and the criminals who threatened public safety.

The Task Force was launched in response to the October 10, 2005 killing of seventeen (17) year old Phillip Haiart, an unintended victim of indiscriminate gunfire exchanged by rival street gangs.

African Mafia street gang associate Jeffrey Hernandez Cansanay was convicted of 2nd degree murder in the killing and was sentenced to fifteen (15) years in prison.

Street Crimes Sergeant Wes Rommel Displays Manitoba Warrior Gang Clothing (PHOTO JGJ)

Operation Clean Sweep was a highly successful initiative reporting an average of over one hundred (100) arrests per month during the early phase of the unit’s operation.  The affected neighbourhoods enjoyed the reprieve from the arson, shootings and the precipitous violence they were experiencing.

The Police Service received significant criticism when they pulled the plug on the highly popular crime fighting initiative.

Enter the Street Crimes Unit.

The Street Crimes Unit was launched to fill the void left by the dissolution of Operation Clean Sweep.

The Street Crimes Unit mandate was indistinguishable from Operation Clean Sweep – quell the violence, suppress the street gang activity and enhance public safety.

The Unit became a force within the Police Service and launched many successful proactive anti street gang operations including Project Falling Star and Project Recall – investigations that resulted in the arrest of dozens of gang members and significant seizures of drugs, cash, guns, ammunition, ballistic vests and other weapons.

Officers who worked in the Street Crimes Unit became highly skilled in the art of informant cultivation, intelligence gathering and covert operations.

Informant cultivation and handling is high jeopardy work that can be both dangerous and complex.


Conversely – gang members, informants, sex trade workers and dedicated criminals put a great deal of energy into corrupting Law Enforcement Officers.

Informant cultivation and handling is a necessary evil that exponentially increases the effectiveness of Law Enforcement.

Corrupting Law Enforcement is a necessary evil that exponentially increases the effectiveness of Organized Crime.

It’s “greasy” work no matter what entity is involved in it.

The First Line

We can’t talk about lines being crossed without being frank in the admission the first line is crossed when a police officer allows him or herself to be compromised.

There is no excuse.

The betrayal of the public trust is egregious and police officers must be held accountable.

Police officers working the right side of the thin blue line often agree the punishment for wayward officers must be more severe than what an average citizen might receive. Serving officers feel a tremendous sense of betrayal when these cases arise, after all, they’re the ones subjected to the public outrage, anger and hostility.

The public just doesn’t get that nobody feels more angry, betrayed, sad, let down, and deceived when an officer is charged with something like this than their fellow officers,” one officer wrote on social media.

There are few professions, aside from Law Enforcement, where the masses are quicker to judge the majority based on the actions of the few.

(Statistics show the number of officers charged with crimes represent a micro percentage of the men and women who serve in Law Enforcement.)

The Second Line

If you consider the defence lawyer perspective, the presumption of innocence and the right to a fair trial may have been the second line that was crossed.

That line was crossed at the police presser by WPS Deputy Chief Danny Smyth who was candid in his remarks to the press;

Deputy Chief Danny Smyth (Photo JGJ)
Deputy Chief Danny Smyth (Photo JGJ)

“Uh initially, I like to believe in our people, and I reacted with disbelief initially. I can tell you during the course of this investigation my emotions have run from disbelief to anger to disappointment to resolve and now here today, to actually some relief that we have brought this member essentially to justice now.”

A defence attorney would tell you, as upsetting and morally reprehensible as this case may be, it’s extremely important for people to remember Constable Milan only stands accused and has the right to be presumed innocent until proven guilty.

It’s the same right enjoyed by every Canadian citizen living within our borders.

Milan also has the right to a fair trial as guaranteed by the Canadian Charter of Rights and Freedoms.

A skilled criminal defence attorney might suggest that right may be infringed when a high-ranking, well-regarded police official essentially convicts the accused person in the court of public opinion by sharing his feelings and belief the officer’s arrest is tantamount to some form of “justice.”

Deputy Smyth continued…

“We recognize that the actions of this one member were inexcusable but they don’t reflect or represent the vast majority of our members who do excellent work with the community and who are engaged with the community on a daily basis.”

The guilt of the officer is certainly implied in the Deputy’s comments.

While the media may appreciate the Deputy Chief’s candor – a criminal defence lawyer might ask – “Is this kind of disclosure appropriate?”

“Is it appropriate if the disclosure removes the officers presumption of innocence or contaminates the jury pool?”

I’ve known Deputy Chief Smyth for almost thirty years and can attest to the fact he’s an intelligent, hardworking, passionate member of the Police Service.

I also understand the need to reassure the public but I wonder what impact his comments to the media might have on a serious ongoing criminal case that has yet to be adjudicated by the Courts.

Time will tell.

The Third Line

The Winnipeg Free Press crossed the third line in a profoundly irresponsible way.

The WFP website is normally my first stop when I look for #breakingnews stories involving crime and punishment.

As I perused the story, penned by respected journalist Kevin Rollason, I was shocked to see a photograph of Constable Milan’s residence in Oakbank, Manitoba.

It was stunning.

Winnipeg Crime Scene (Photo JGJ)
Some Lines Shouldn’t be Crossed (Photo JGJ)

I wondered what argument could have possibly been made to justify inserting the photograph into the story.

Does the photograph add substance or enhance the story some how?

Does the public have a right to know, or in this case, see a photograph of the accused officer’s family home?

Does the public have a right to know where the officer and his family live?

Surely the Editor would have known the publication of the photograph could pose significant safety risks to Milan, his wife, siblings, parents, in-laws or anyone else who may be present at his home.

It’s not a big stretch to assume Constable Milan may have the odd enemy or two after working in a unit known to target violent gang members and street thugs.

Assuming the allegations against him have merit, it’s even more likely the publication of the photograph has raised the danger he and his family now face.

I’d be interested to hear the justification.

The Final Word

I’ll leave the last word to Winnipeg Police Association President Maurice Sabourin who put the officer’s arrest into context;

“The thing I would like to get across to the citizens of Winnipeg is that you shouldn’t lose any confidence in the Winnipeg Police Service because our members are committed to protecting and serving the citizens of Winnipeg and this is an isolated incident.”

The Press Release


WPS Media Release
WPS Media Release


I do not personally know Constable Trent Milan and do not recall ever having met him.

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  1. James G Jewell


    Thank you for adding your perspective.

    Appreciate your opinion.

  2. Manuela Lima

    I only found out about Mr. Milan’s untimely passing less than two weeks ago. As I knew him when he was a child — and my son’s very good friend — I felt deeply saddened by this news and went “on line” for the sole purpose of reading his obituary. Needless to say, his obituary was the only article which spoke of Trent Milan as a most beloved son and husband, and as the friend and neighbour those who knew him could not forget.
    The rest was a myriad of trashy comments and cruel judgments about a man who, during a news conference, was directly attacked by the WPS. What happened to the usual commentary along the lines of “We cannot, and will not, comment on what has occurred until a full investigation is completed.” Where did the proverbial “Blue Wall” go? And how many other police officers have been investigated for what Mr. Milan was accused of — or worse? That Smyth had the nerve to speak about Trent Milan as he did is unacceptable. His self-righteous verbosity clearly tainted the jury pool. And that he felt relief at what had occurred left me quite confused. Was he relieved because Trent Milan had died and, as such, had taken to the grave what he knew about other violators in the WPS? Or was he relieved because a “dirty cop” in the WPS had done the right thing by dying? Either way, Smyth’s comments were inexcusable and prejudicial. In so much as he tore Milan to bits, he should have been publicly berated by his own superiors.

    Now to another inexcusable event: the newspaper publication of a photo of the Milan residence. What an irresponsible editorial decision! In view of the violations Milan had been accused of committing, showing the public where he lived and what his residence looked like is as serious as if the paper had deliberately armed an angry gang of derelicts with automatic weapons and given them strict instructions to aim and shoot at the house or at anyone in or around the Milan residence. How disgusting! What purpose did publishing that photo serve? Everyone talks about freedom, yet have no idea what it really means. Freedom comes at a very steep price: responsibility. Freedom of the press cannot be protected if or when lives are at risk in view of the information published by that same press. Somehow, many people still live under the impression that freedom of speech and freedom of the press are a given and, as such, are not associated with responsible behaviour or the responsible use of the written word. Wrong!

    I hope time and the love of family and friends manages to diminish the pain of losing a loved one, regardless the circumstances.

    Sent by Manuela Lima, Victoria, BC, November 6, 2016

  3. James G Jewell


    I know the culture in the Police world and don’t believe for minute a bunch of people knew about this and were keeping it under wraps. Conversely, my understanding is the situation was exposed by the “boys in blue” to use your term. That undermines the conclusion you make in your comment.

    I can also tell you I know currently serving Police Officers who knew Milan quite well and were shocked by the news of his arrest.

    Officers do work in pairs most of the time but, as this case proves, some people are very skilled when it comes to living a double life.

    Thanks for commenting.

  4. I find the whole This situation with this officer to be quite astonishing to say the least. If the police took all these years to finally catch one of their own what does that say. I also find it weird that he did this all by himself with no other officers involved. I’m sure someone on the force knows more than what we are been told. We keep hearing how the boys in blue are a close knit group, But we’ll never know as dead men can’t speak. Don’t officers work in pairs most of the time !

  5. Wayne Macaulay

    Milan took the easy way out, possibly to spare his family the details of his alleged crimes.

    Does Milan’s family qualify for benefits depending on suicide or just bad luck crashing into a tri-axle gravel truck?
    I hope they do as they are innocent bystanders in this tragic case.

    I take exception to comparing his alleged charges versus his 18 years of service to the citizens of Winnipeg. That’s the tough job he undertook as his career choice. He appears to have failed miserably.

    To expect sympathy or gratitude for Milan because he happens to be a Cop just doesn’t cut it. The allegations are numerous and disturbing.

    My sympathy goes to his family.

  6. I disagree with the way the WPS handled the announcement of charges brought against Mr. Milan. The implied guilt with matter of fact statements is troubling on more than one level. While I agree that police officers must be held to a higher standard, I believe everyone is owed a fair, unbiased legal proceeding, of which Mr. Milan was deprived.

    I’m also extremely disappointed with how the media published the location of Mr. Milans home. It was unnecessary and reckless and added nothing to the story.

    So now it appears Mr. Milan has taken his own life. Yes, I’m making an assumption.

    This is sad. If Mr. Milan was in fact guilty of the charges laid against him, he surely screwed up and made some significant errors in judgement. However, I suspect Mr. Milans service to the City of Winnipeg and its citizens over his 18 year career far surpass the actions he’s accused of.

    My condolences to his family, and friends.


  7. Thanks James. I was afraid that might be the case.

  8. James G Jewell


    The WPA would evaluate the case and come to a decision regarding providing support and/or funding for the Officer’s legal fees.

    It’s my understanding that if overwhelming evidence suggested the Officer’s guilt, that funding would not likely be provided.

    Of course, without the funding, the financial obligations placed on the officer would be crushing.

  9. I’m with you on the innocent until proven guilty, and I’d go a step further. Does the Police Association have any role in something like this? Would any supports have been provided?

  10. I think it was actually television news, but one of the news agencies actually clearly posted the numbers displayed on what is believed to be his house.. They also interviewed his neighbour..

    Oak bank is not that large and with the photos of the house and the number of the house. I think i could find it in an hour..

    I don’t know how his house and number adds substance to this story.

  11. James G Jewell


    If you saw the article in the Free Press you would know the photo caption divulged the fact the residence was in Oakbank.

    No other lines crossed.

  12. How many residents in Winnipeg and the surrounding area would know where this house is just by looking at a picture? There wasn’t a house number or a street name in the photo. It is this article that has outed the Oakbank location of Milan’s family and possible guests. Is this a fourth line crossed or a release of confidential information to justify and ensure WPS protection for the family? Risky, careless and brazen…retirement has served us all.

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