The time, the place and the victim were all wrong.

But there was no mistake: Someone had targeted 37-year-old tech exec Matthew Staikos for death.

And cops suspect the motive was personal.

Staikos was found fatally wounded by emergency personnel responding to reports of gunshots at Bay St. and Yorkville Ave. around 11:30 p.m. on May 28, 2018.

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The family of Matthew Staikos has offered a $250,000 reward for any information leading to the capture of the gunman who murdered him.Photo by Jack Boland illustration /Toronto Sun

Cops say at least three gunshots were fired after the triggerman jumped out of a Mercedes and started firing. One bullet hit Staikos in the back, another in the head.

“This was an obviously targeted event,” Toronto Police cold case boss Det. Sgt. Steve Smith told the Toronto Sun. “Someone in the community knows why he was murdered and we’re asking them to come forward.”

Smith noted that unsolved murders are usually solved by new technology and the changing nature of people’s relationships.

He could add a get-out-of-jail-free card.

IDSINGA AN AMAZING LEADER: Toronto Police Det. Sgt. Steve Smith, head of the cold case unit, has solved three of the GTAs most heartbreaking murders.
Toronto Police Det. Sgt. Steve Smith, head of the cold case unit.Photo by BRAD HUNTER /TORONTO SUN

“There was something in his personal life that precipitated his death,” Smith said. “We don’t intend on stopping until we find out why Matthew Staikos was murdered and bring the killers to justice.”

At the time, cops collected video surveillance from the area. They’re looking for a gunman described as Black and 5-foot-10 with a medium build.

The murderer fled in a silver or grey four-door Mercedes.

Smith said detectives don’t believe Staikos knew his killer. Instead, they believe the gunman was a hired hand with someone else in the background pulling the strings — and the figurative trigger.

Successful real estate broker Simon Giannini, 54, was gunned down while dining at Michael's On Simcoe Restaurant on Saturday, Sept. 16, 2017. (Facebook photo)
Successful real estate broker Simon Giannini, 54, was gunned down while dining at Michael’s On Simcoe Restaurant on Saturday, Sept. 16, 2017. (Facebook photo)

And there is a twist: Nine months before Staikos was murdered, another local businessman died in an equally brazen hit at a downtown steakhouse. The M.O. had the same stench, down to the description of the killer.

On Saturday, Sept. 16, 2017, around 8:50 p.m., cops responded to a shooting at posh Michael’s Steakhouse at Adelaide St. W. and Simcoe St. Real estate agent Simon Giannini, 54, died shortly after he was brought to hospital.

Cops have noted the similarities but have typically pooh-pooed any connection between the two slayings.

As for Staikos, in the annals of victimology, he would certainly fall into the least likely category.

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Matthew Staikos was shot dead in Yorkville in May 2018. FACEBOOK

Handsome, charming, smart and well-liked by friends and colleagues in the tech industry, Staikos graduated from the University of Toronto in mechanical and computer engineering.

At the time of his death, he was CEO of the internet messaging site Vleepo. Previously, he founded mobile application developer Torch Mobile, later acquired by Waterloo-based Research in Motion.

“None of this makes any sense at all,” a friend told the Sun in 2018.

One former colleague and friend from the tech industry was equally befuddled.

“People can’t understand it … he was good-looking, nice, girls loved him … everybody loved him,” the former co-worker said. “Everyone’s flabbergasted.”

The friend added: “No gambling, no drugs, he was soft-spoken, just a really nice guy … maybe it was a case of mistaken identity. Nothing else makes any sense.”

Matthew Staikos was homicide number 38 in 2018.

If you have any information regarding this case, contact the TPS Homicide unit at 416-808-7400, or [email protected]. You can also contact Crime Stoppers anonymously at 416−222−TIPS (8477); or via the internet at 222tips.com.

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@HunterTOSun