Sean Orman was once foiled during a £17,000 raid at an Edinburgh jewellers after being tackled by an ex-police officer known as Robocop.
Orman was fleeing from the heist at Laings in Frederick Street when he was bundled to the ground by Ray Mallon.
The former Middlesbrough mayor, previously a senior officer whose tough stance on crime earned him the nickname, had been window shopping at the time in January 2014.
Mallon said: “I noticed a commotion inside. Suddenly a man came sprinting out the door with two assistants chasing after him.
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“I stepped across the man and we grabbed hold of each other and wrestled for a few seconds. I managed to get him in a headlock and we ended up on the ground.”
Orman later pleaded guilty to stealing two watches worth £17,000.
In February 2015, Orman was jailed for five years for targeting Edinburgh bookmakers in three armed raids which netted a total of more than £1800.
He was caught after the final robbery when a customer noted his getaway car details.
A jail source said Orman’s crimes were usually carried out to pay for heroin.
The source said: “Orman’s a junkie and was seemingly willing to take any risks to score.
“When he got out of prison in February he went straight back to crime, which wasn’t surprising. But this time he was willing to kill people for money.
“He worked as a joiner once, but after the drugs took hold he became increasingly horrible.
“His earlier offending showed a self-destructive streak where he almost wanted to get caught. With this murder it does seem like he no longer cared about anyone, even himself.”
But Orman still had an eye for an expensive watch. When arrested in April 2019 following a high-speed chase, he was wearing a Hublot watch which sells for upwards of £3000.