Having risen through the ranks of Manchester United's academy over the years, Simpson was a well-known face to the club's senior pros by the time he broke into the first team.
As a defender, the likes of Wes Brown and Patrice Evra took Simpson under their wing as they helped him make the transition from academy to men's football.
It soon came time for Simpson to upgrade his contract to a professional one in order for him to further his development.
But as a Red Devils youngster, few things were scarier than talking about contract details with Ferguson.
After all, this was a man who branded the late Mino Raiola - Paul Pogba's former agent - a 's***bag' in his 2015 autobiography.
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Simpson, desperate to avoid falling on the wrong side of Ferguson, decided to avoid bringing in agent to the discussions for his new United deal.
Instead, he got one of his teammates, who just happened to be the club captain at the time, to do the deal.
"Gary Neville actually negotiated my contract with Fergie," Simpson told talkSPORT's Inside Devils.
"As a young kid, when you're starting to knock on the door and get around the first team, you're scared that you're going to annoy him.
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"He'd go, 'I want to give you a new contract,' and you'd say to him, 'My agent will see you.' You were scared to say that. Whereas now it's the first thing you say.
"I'm thinking, 'If I say that, he's going to bin me off.' So I spoke to Gaz and Gaz was like, 'I'll go see him for you.'"
The timing of the contract happened right before Simpson was due to join Sunderland, managed by Red Devils icon Roy Keane at the time, in January 2007.
For the deal to go through, Simpson had to change from a scholar to a professional.
"It was me, Gaz and Sir Alex in the room," Simpson said.
"I didn't really know what to do. So I'm just sat there in the middle.
"He (Neville) actually got me more money, to be fair. He actually didn't [ask for a cut].
"The Gaz that you see now is always that Gaz."
Simpson ultimately made eight appearances for United across the five seasons he was on their books, with the majority of his time at Old Trafford spent on loan.
He secured a permanent move to Newcastle in January 2010 before joining Queens Park Rangers in 2013.
But the most memorable spell of Simpson's career came in August 2014 when he joined Leicester City.
He played a key role in helping the Foxes pull off a miracle to avoid relegation in his first season at the club.
Simpson then started 30 league games the following term in Leicester's unthinkable Premier League-winning campaign under Claudio Ranieri.
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The right-back featured in six of the Foxes' nine Champions League fixtures the following season and eventually departed in 2019.
Listen to the full episode of Inside Devils on YouTube.