Cheltenham rising star Josh Lai training with Port Adelaide for SSP list spot

It was purely by chance that Port Adelaide recruiters spotted Josh Lai on Anzac Day. After that game, they’d covertly watch him six more times. PAUL AMY has the inside story of Port’s SSP bolter.

They found Josh Lai at a suburban ground on Anzac Day.

Port Adelaide AFL recruiters Geoff Parker and Brett Anderson went to the Southern league Division 1 game between Cheltenham and Bentleigh this year not to scout, but to take in a day of local football.

Anderson is a Cheltenham life member and his family has strong ties to the club.

As he and Parker watched the match, their eyes were often drawn to the Chelt player in the No. 41 jumper on the wing, the strongly-built Lai.

His twin brother, Sean, a left-footer, was wearing No. 42.

As Anderson tells the story, by halftime he and Parker knew they had come across an exciting young player.

Josh Lai was spotted playing local footy for Cheltenham.

Josh Lai launches Cheltenham forward during the Southern footy league Grand Final. Picture: Andrew Batsch

No footage of the match exists – there was apparently a mix-up of dates with the company that films Southern fixtures – but Lai finished it as the clear best-afield with about 30 possessions. It was only his second game of senior football.

The recruiters decided to track his progress. When they turned up six months later to watch Lai play in the grand final, they had fellow Port Adelaide recruiter Robbie Gray with them.

Lai played up to their hopes, winning the medal for best-on-ground.

The day after the rookie draft, Port Adelaide phoned the 19-year-old, asking two things: would he undergo a medical and was he interested in training with the club as a potential SSP rookie.

Lai was in his birthplace, Singapore, when the call came and was taken aback. But he answered yes to both questions.

After getting the all-clear for the medical, he set off for Adelaide, filling a spare room at the home of Power player Miles Bergman.

Lai’s appearance on permission-to-train lists has set off the prospect of a local footballer who has played only a dozen senior games being elevated to an AFL list.

“Amazing … very surprising,’’ one top VFL club official remarked when the Herald Sun reported Port’s interest in Lai.

Cheltenham president Adam King agrees it turned a few heads, but only because the path from local football to the AFL is so rarely stepped.

A player’s journey typically takes in the elite Under 18 competition or a state league, such as the VFL.

“It’s not the normal pathway, a 19-year-old kid coming out of suburban footy,’’ King says.

“The safest option for an AFL club seems to be picking them from the Coates League or waiting for them in the VFL system if they want someone a bit mature.

“But if people saw what he did in 12 games with us … they would have seen his capabilities and that there’s a lot of upside to him. I think it’s the pathway side of it that throws people out.’’

King had known of Port Adelaide’s interest in Lai for months, but stayed quiet.

He did not want the young player finding out and being distracted.

“All we wanted was for him was to go out there and enjoy it and be a free spirit,’’ King says.

Port Adelaide watched Lai “live’’ six times during the season. It was also keen to keep things quiet as it weighed up the first-year Rosella.

Josh Lai kicks goal for Cheltenham

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The Lai brothers were raised in Beijing and came with their family to Australia in 2012.

Initially they played soccer, but friends drew them into football at East Sandringham and then Hampton Rovers juniors.

Attending Mentone Grammar, they were coached by Paul Kennedy in years 10 and 11. St Kilda, through its multicultural program, and the Sandringham Dragons showed fleeting interest in the brothers.

At Kennedy’s urging, they went to Cheltenham in 2023 to play senior football under the coaching of former Richmond defender Des Ryan (Kennedy and Ryan were teammates at VFL club Frankston and have remained close).

Sean was the first of the twins to come through, parading a penetrating left-foot off a back flank, earning a call-up to the Oakleigh Chargers in the Coates Talent League and attracting the attention of Richmond VFL, where he trained but was not listed.

Josh and Sean Lai after this year's Southern league grand final.

Josh played only a handful of games last year because of stress fractures in his foot.

But Cheltenham understood him to be a promising player.

He showed as much in a practice match this year, but he was picked in the Under 19s in Round 1. He made his senior debut in Round 3 and finished the season with 12 games, seven mentions in the best, a premiership medal and Chelt’s rising star award (Sean had won it 12 months earlier).

Anderson and Parker saw in him “traits’’ they thought could be transferred from level to level, starting with his willingness to compete.

They also noted his speed and power, and ability to take a strong mark and gather ground balls.

There was also a “change of gears’’ and a quiet confidence apparent when he saw a gap and took it.

King makes another observation: “He’s as tough as nails. Goes back with the flight, takes a hit when he has to.’’

Through its bright young recruiter Oliver Grant, Richmond became aware of Lai and arranged for both brothers to train with its VFL squad with a view to being listed for 2025.

Port Adelaide knew of the Tigers’ interest in Josh and spoke to Grant about him. He had appeared on no other recruiting radars.

Josh Lair accepts his medal after the Southern football league grand final. Picture: Andrew Batsch

Port is happy to give the suburban smoky a go.

It also has North Melbourne VFL captain Jack Watkins training for an SSP slot. Watkins has risen in the state league despite being lopped from Werribee’s list at the end of 2020.

“No two stories are the same,’’ Anderson, a former editor of Inside Football, says.

“There’s no right or wrong way (to make an AFL list). It’s opportunity, it’s talent, competitiveness and work ethic. Both Josh and Jack have fantastic yet different stories and the same opportunity.’’

Since coming out of Covid, Cheltenham has had Austin Johnson (Richmond), Sam Hayes (Northern Bullants), Declan McComb and Ollie Moran (Frankston) progress to the VFL.

McComb and Moran were part of a Mentone Grammar group that joined the Rosellas, as was Finn Ryan.

King says it has been exciting time for his club, winning the 2023-24 premierships and attracting talented youngsters to blend in with seasoned locals and former AFL and VFL players, including Jack Lonie, Dylan Weickhardt, Sam Dunell and Jacob Edwards.

“From our end, we’ve given boys the opportunity to play senior footy at a young age and have some really good senior footballers around them who are prepared to teach and help develop them,’’ King says.

“We want these kids to push on to a high level. That’s why we’re so rapt that Josh has got this great opportunity. I think stories like this give hope to a lot of other players who don’t come through the standard system.’’

Originally published as Cheltenham rising star Josh Lai training with Port Adelaide for SSP list spot