Not only did the Echuca product etch his name into AFL folklore, but the gun midfielder became the first Goulburn Valley League export to claim the prestigious award.
Wines, 26, polled a record-equalling 36 votes — three ahead of Western Bulldogs captain Marcus Bontempelli.
Remarkably, it was the first time four players had polled more than 30 votes, with Mooroopna and Echuca product Clayton Oliver (31) and Carlton's Sam Walsh (30) finishing inside the top-five.
In a thrilling finish to the vote count, Wines edged out Bontempelli in the final round.
Two votes in the round 23 win over the Bulldogs ensured Wines the league's highest individual honour.
In doing so he became the first Port Adelaide footballer to take home “Charlie”.
“I'm a little bit rattled, to be honest, still,” Wines said on stage.
“There are so many great players that I still look up to at my age, who have had tremendous seasons, a lot of them are obviously playing on Saturday in the biggest game of the year.
“I'm extremely envious of them and I'd love to be in their position.
“But as you said it wasn't to be this year and I know we'll rebound and go again next year.”
Wines polled in a record 16 games and stormed home with votes in 11 of the last 12 rounds.
He managed to pinch the lead from Bontempelli in round 22.
The win bookends a career-best year for Wines, who averaged 32 touches and was a driving influence in the Port engine room as it made this year's preliminary final.
Wines thanked Port Adelaide, his teammates and the town of Echuca, which he was “sure is up and about” after the win.
Speaking at a press conference following the vote count, Wines said Echuca co-coach Andrew Walker was one of his idols growing up and he hoped to inspire the next generation of Murray Bombers.
“When I was a kid, I watched Andrew Walker and these guys and aspired to be like them,” he said.
“I know Mum and Dad, when they're in town, go into the grocery shop and they've always got parents coming up to them saying how much their kids love watching me and passing on footy cards for me to sign.
“If I can inspire those young kids from my town, who perhaps don't get as much opportunity as the kids in the city, I think I'm doing my job well.”
Meanwhile, it was a memorable night for Wines’ former Echuca Football Club junior teammate.
Clayton Oliver ended up on the podium with 31 votes after a dominant season.
The Melbourne jet, who is preparing for this weekend's grand final, held the lead at round 12 before Bontempelli went on a hot streak.
Elsewhere, Seymour product David Mundy capped his sublime campaign.
The Fremantle veteran polled 20 votes in his 18th year in the competition.
At 36, Mundy became the oldest player in history to poll more than 20 votes.
It was also the classy operator's highest tally in his career.
A total of six exports from the Goulburn Murray region polled a vote in this year's Brownlow Medal.
Finley's Tom Hawkins managed six votes, while Euroa's Jamie Elliott (three) and Mooroopna's Jy Simpkin (one) rounded out the remaining talents who polled.
Goulburn Murray region exports
Ollie Wines (Echuca) — 36
Clayton Oliver (Echuca/Mooroopna) — 31
David Mundy (Seymour) — 20
Tom Hawkins (Finley) — 6
Jamie Elliott (Euroa) — 3
Jy Simpkin (Mooroopna) — 1
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