It is part of football folklore that Jude Bolton’s boyish good looks saved him from a career in the black, teal and white of Port Adelaide.

In the lead-up to the 1998 national draft, Power coach Mark Williams was keen on snaring the fresh-faced Bolton.

But, despite Bolton’s impressive football CV, Williams overlooked the youngster because of what often has been described as his “pretty boy” image.

What Williams did not realise was that although Bolton had the face of a choir-boy, he had the heart of an ox.

The Power had the number seven selection at the 1998 draft and, instead of naming Bolton, selected West Australian Josh Carr.

The Swans swooped with their number eight choice and, in Bolton, secured the services of a youngster who would become one of the toughest nuts in football.

Bolton played 325 games and kicked 196 goals for the Swans from 1999-2013, with the 2005 and 2012 premierships his career highlights.

His dual premiership appearances put him in truly elite company as he is just one of five South Melbourne/Sydney Swans players to win two premiership medallions.

The others are Vic Belcher (1909 and 1918) and Bolton’s teammates Adam Goodes, Ryan O’Keefe and Lewis Roberts-Thomson.

Bolton, named after the main character in Thomas Hardy’s novel “Jude the Obscure”, was just 19 years of age when he made his AFL debut in the Round 12 match against Carlton at Princes Park, on June 20, 1999.

It was a modest beginning as Bolton had just six disposals (three kicks and three handpasses). But, more importantly, the teenager from Aberfeldie and the Calder Cannons played in a winning side, with the Swans triumphant by 27 points.

Bolton played nine senior games in his debut season and, from there, he became an integral part of a Swans team on the rise.

He won a Rising Star nomination in 2000 and quickly established himself as one of the most prolific ball-winners in the competition.

Bolton finished third in the 2003 club best and fairest and played his 100^th AFL match when he lined up against Hawthorn at the SCG in 2004; the Swans won by a point.

And who could forget Bolton’s efforts in the 2005 Grand Final triumph over the West Coast Eagles?

He might have had his head split open to finish the match wearing a head-guard, but his 14 possessions and hard work around the packs were pivotal in the victory.

The milestones continued and in, 2008, he played his 200^th game for the Swans, against Melbourne at Canberra’s Manuka Oval. The Swans again triumphed, this time by 40 points.

Then, late in 2012, he became one of only three Swans players to play 300 games in the red and white, along with Adam Goodes (372) and Michael O’Loughlin (303).

This milestone was in the preliminary final win over Collingwood at Sydney’s ANZ Stadium.

Of course, his next game, was in the 10-point 2012 Grand Final victory over Hawthorn.

Bolton retired at the end of the 2013 season with 315 games to his credit, behind only the remarkable Goodes (372 games from 1999-2015).

As the sun set on his career, Bolton never slowed down. He set an AFL record in Round 3, 2011, against West Coast for the most tackles in a game by an individual player (19).

It still stands, but he shares the accolade with Tom Liberatore (Western Bulldogs) and Jack Ziebell (North Melbourne) who both equalled that tally earlier this season.

Early in Bolton’s Swans career then assistant coach Ross Lyon remarked that Bolton might have entered AFL football looking “pretty”, but would not bow out that way because of the way he played. That is: see ball, get ball, no matter the consequences.

Lyon was wrong; Bolton retired with his good looks intact and with a reputation as one of finest footballers ever to play in the red and white.