Jack Sinclair could buy anything under the sun for his mum, Kerrie, this Mother’s Day, but there’s no gift that could compare to him running out in his 150^th game for St Kilda this weekend. That, “and a win”, Kerrie says.

Sunday’s game will be a true family affair at Adelaide Oval. Kerrie, Sinclair’s sister, Georgia, and her husband, alongside many other family members will be making the trip over the border for the latest milestone, before soaking up the occasion with a celebratory dinner at the ground, which Sinclair will be in attendance for post-game.

In many ways though, this weekend’s interstate expedition isn’t too far off from the usual.

Kerrie travels across the country to see her son in action and has missed less than a handful of games outside of 2020, can list photos of him off the top of her head (and recall exactly what games they’re from), plus knows the Saints’ past and present players inside and out.

She’s Jack Sinclair’s biggest fan, and she couldn’t be prouder of him.

The celebrations come with a poignant undertone for Kerrie in particular given her family’s connection to the red, white and black. Her father, Bill Gleeson, played 15 games for St Kilda between 1955-1956; his time at the club the impetus behind Sinclair’s childhood desire to follow in his grandfather’s footsteps.  

“It’s a dream come true for me. I had no idea he was going to land at St Kilda, but boy, I wish my dad were alive now to see him now,” she told saints.com.au in the lead-up to her son’s milestone game.

“It’s incredible even to think where he’s come from being a rookie. I was thinking about it the other day how Jarryn Geary was a rookie, Stephen Milne was a rookie… it’s an amazing achievement to be drafted first as a rookie and then go on to play for so long.”

Between Sinclair’s latest milestone – his 100^th game in 2021 wherein he was presented his guernsey by football legend Tony Lockett – and today have been 50 games of matchless class.

A reinvention into a precise and composed half-back that year unlocked No. 35’s best, seeing him piece together a prolific campaign to become one of the Saints’ best players whose importance to his side’s ball movement and transition were paramount.

The move to-date has yielded a maiden Trevor Barker Award and All-Australian selection (both in 2022), plus a runner-up finish at Best & Fairest and the Robert Harvey Best Clubman Award the season prior.

This year appears to be cut exactly from the same cloth. He’s equal-ninth in the coaches’ votes after eight rounds, is in line for another top-end finish at this year’s Trevor Barker Award and could have another stitching added to his maiden All-Australian blazer if he keeps going the way he is currently.

This weekend’s milestone is the latest etching into a boyhood dream that he and his family hold so dear.

Although Sinclair stresses that while he always wanted to play for St Kilda, was actually a Carlton fan growing up (and as it turns out, brief Port Adelaide supporter after their 2004 Grand Final triumph), Kerrie reassures her son has “always been a Saint at heart”. And not just from a colours sense.

“He’s always been a kid that’s always done the right thing, he’s got a lot of empathy and he’s very caring, so I think that’s held him in good stead,” Kerrie said.

“I do this remember this great photo of Jack and Paddy McCartin after Paddy had a concussion. They were coming off the ground together and he put his arm around him… it’s just the look of concern on his face and I thought ‘that’s just typical Jack’.”

“Jack’s so diligent in everything he does. Even as a small boy he always wanted to please everybody… but he’s very modest.

Away from the field, Sinclair is quite easily one of the most relaxed customers going around. He’s keen on his gaming, doesn’t mind a bit of Dua Lipa and more often than not is kicking back with housemate Dan McKenzie and dog Virgil.   

But the laidback exterior gives zero indication as to just how hard he’s had to work to get to where he is now.

It was only three seasons ago that Sinclair, a mainstay of the side, was omitted from the team and had to claw his way back in as a pinch-hitting, pacey utility.

Before that, he had fought tooth and nail to make it to the league in the first place as an over-ager via the rookie draft. That’s not to mention the challenges in form, opportunity and consolidating a place in the side after eventually getting picked up.

“AFL footy’s good at bringing you down a peg pretty quickly. It’s definitely had its challenges but I’m so grateful to be able to play this many games,” Sinclair told saints.com.au.

“It’s definitely had its ups and downs, but the last few years have definitely been easier on a personal level to play some better footy and be playing every week.

“I think I’ve exceeded expectations coming in as a rookie when I was 19, but I certainly had the belief I could become a far better player.

“Maybe for people on the outside might see (the past few years) as a surprise, but certainly for myself and those who have seen me play closely, I don’t think they’re too surprised.”

Now, the years of persistence have paid off. Unsurprisingly, his mum is one of those who always knew he was capable of reaching the heights he has.

“Mum’s a very supportive person, she’s barely missed a game, is always travelling to games and is always encouraging me,” Sinclair said.

“She’s always loved the footy club and has very fond memories. I know how proud she is to see me wear the same jumper as my pop.

“It’s clearly something I really love and it’s probably off the back of how much enjoyment I’ve got from having my family there with me.”

Nonchalant as he may be, the sentiment of reaching such the 150-game mark and fulfilling his boyhood reverie is still there for Sinclair.

A signed photo of childhood-hero-turned-coach Robert Harvey which he’s had since he was a youngster is nestled away in his bedroom, accompanied by his Best & Fairest medal and another picture of Sinclair and his family from the same night.

Staggeringly, this weekend’s milestone is not even half the amount of Harvey’s 383 games. However many games are left though, there’s a fair chance to be more accolades to follow in time for the modern-day No. 35.

“There’s a great photo of Jack and Robert Harvey in the rooms after a game against Richmond… I can’t remember how many games he’d played at that point, but I remember he said afterwards ‘only 300 and something games to go!’,” Kerrie said.

“He loves Robert Harvey. As a kid, he had this photo of Robert that his uncle got signed of him… he’s got that at home next to his Best & Fairest. It’s just amazing.

“There was a lot of pressure taking that number on. He didn’t say that himself, but taking on a legacy like that, everyone thinks ‘no-one will be able to replicate Robert Harvey’.

“But he’s doing a pretty good job. He’s serving that number well.”