McGregor, while perhaps not the prettiest player to grace the AFL scene, has proven one of the most long lasting with his hard, team-first, strong-marking style of play.
The rugged forward is undoubtedly one of the most popular players at West Lakes and when he runs out onto AAMI Stadium on Saturday, McGregor will become just the 11th Crow to reach the 150-game milestone.
"It's an achievement I never really thought I would make, it kind of creeps up on you,” he said.
“I only started thinking about it this season and to finally get there- it feels fantastic.”
McGregor was drafted by Adelaide in 1998 and, in his 10 years at the club has only completed a full season at AFL level once, in 2005.
The 26-year-old has overcome injury and form concerns to become one of the most dependable forwards in the Crows’ history.
McGregor averages a goal a game and last week climbed into 13th position on Adelaide’s all-time leading goal-kickers list.
Teammate Michael Doughty, who joined the Crows one year after McGregor, said the 150-game milestone was a credit to ‘Kenny’s’ perseverance.
“Kenny’s a good team man and all the boys love to get around him, so for his 150th game I’m sure we’ll make a special effort, as we do every week,” he said.
“We always want to win milestone games and we want Kenny to really remember the day.
“He’s always been one of those blokes that gives everything at training and in the pre-season.
“He works hard, especially for a big bloke, so to see him get to the 150 over 10 years is a really great, committed effort. He definitely deserves it.”
McGregor, who finished fourth in the club’s goal kicking despite playing just nine games last year, contemplated leaving his beloved Crows in the off-season.
But coach Neil Craig was adamant McGregor, a cadet journalist with the Advertiser, was a required player at West Lakes and McGregor is thrilled with his decision to stay.
"I never got my head around leaving the club and it's something I never really wanted to do,” McGregor said.
“I love this club and I love playing here, so to play 150 games for the Adelaide Football Club … I'm just so happy to be able to do it.”