Back in the mid-noughties, Simpson cemented legendary status by orchestrating Carlisle's quickfire rise from the Conference to League One.
And in 2022, 16 years after leaving for Preston, he became a hometown hero all over again, saving the Cumbrians from relegation to the National League before winning an against-all-odds play-off final against big-spending Stockport the following season.
Then, the wheels came off. Carlisle won just seven games in League One last term and were relegated in April having spent three solid months at the foot of the table.
A new ownership group initially backed Simpson, but a slow start saw him sacked just four games into the current season.
"It's been a very tough 2024, and losing my job did hurt," says the former Manchester City winger, who also played for Oxford and Derby before embarking on a 22-year career in coaching and management that includes winning the Under-20 World Cup with England in 2017.
"But I'm not scarred by it, which can happen sometimes.
I remember when I finished at Stockport in 2011. That was such a horrible experience for me I actually questioned whether I ever wanted to get back into football at all.
"I don't feel that wa with Carlisle. I look back and I'm massively proud. That first 15 games when we stayed up was an incredible experience, as big an achievement as anything I've done in my whole career.
"To see the whole of the city and the local area coming back together nothing tops that.
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