A Superior Court judge has criticized Toronto police for an “ill-conceived” decision not to arrest a purported gang leader who allegedly went on four days later to shoot two teenagers in broad daylight.

Investigators had decided April 15, 2004, to intercept Tyshan Riley’s phone calls rather than arrest him, even though he had been implicated in several shootings by confidential informants and a friend and was seen to be breaching bail conditions from an unrelated charge.

Riley, said to be the leader of the Galloway Boys, was eventually arrested on April 19, 2004, about 90 minutes after allegedly shooting the teenagers at a townhouse complex in the Malvern area of Scarborough. The young men, who were not gang members, were each hit multiple times, but survived.

One of the intercepted communications “apparently captured Riley describing the shooting … as it happened,” Superior Court Justice Michael Dambrot wrote in a ruling last October.

Earlier police wiretaps of phones belonging to members of Riley’s hated rivals, the Malvern Crew, had been buzzing with talk of his incursions into the neighbourhood. The wires picked up one unidentified man telling Malvern leader David Francis March 31, 2004, that Riley had brandished his pistol “in my face” at the Malvern Mall.

So in mid-April, Toronto police took the rare, but legal step of intercepting Riley’s phone calls without first obtaining a judge’s permission. While investigators wanted to prevent Riley from shooting someone, they felt they could build a better case against him if they tapped his lines and kept him under surveillance. Unfortunately, it didn’t work out that way.

In fact, the judge at the trial where Riley stands accused of murder has described that police decision as “ill-conceived.”

Arresting Riley, “a man with a serious record for violence … would have succeeded in preventing him from shooting anyone else,” Dambrot concluded last summer in a ruling that up until now has been covered by a publication ban.

Before the trial, Dambrot ruled the Riley wiretaps inadmissible because police had not shown they intercepted the phone calls “to pre­vent serious harm to persons”.

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