Steve Bruce feared his decision to turn down Newcastle as they fought to sign Wayne Rooney would haunt him forever.
The 58-year-old will send his hometown club into Premier League battle with Arsenal on Sunday almost 15 years after he rejected the opportunity to replace Sir Bobby Robson at the helm, with then chairman Freddy Shepherd rivalling Manchester United for Rooney's signature.
It was a decision Bruce, then in charge at Birmingham, lived to regret until he finally got the opportunity to say yes for a second time.
He said: "I regretted it when I didn't take it before, especially with what happened with Birmingham because within a year, they had sold it to Chinese owners and everything that was in front of me that I thought I was building was gone.
"So I regretted it because there was a great opportunity as well at the time. At the time, to be fair to Freddy, he was trying to buy Wayne Rooney.
"Would I have Wayne Rooney as my first signing? 'Are you for real Freddy?'. I regretted it and thought I would regret it for evermore."
Bruce never played for Newcastle having been overlooked as a youngster and then snapped up by Manchester United after proving his quality at Gillingham and Norwich.
Even when the call came to replace Rafael Benitez last month, he was not entirely convinced it was genuine.
He said: "I don't know if any of you know my lawyer, but he's quite reserved. Typical lawyer, he's got no real sense of humour about him!
"When he picked up the phone, I did say to him, 'Matthew, are you taking the p*** out of me?'. He said, 'No, I've got to ask you if you'd be interested'.
"I was in Portugal trying to prepare another team. I said, 'Is it for real?', he said, 'Yeah, they want to talk to you and meet you as quickly as they possibly can'.
"It happened like that, within 24 hours. It was quite remarkable."
Bruce's first game will be tinged with sadness, with his parents Joe and Sheenagh, who died within three months of each other last year, conspicuous by their absence among the family members who will attend.
He said: "He never wanted me to go into management, my dad, he thought it was too stressful. He was probably right! My mam was a different animal, she went from when I was kid, until...
"She'd be there."