Stynes was quite famous in both Australia and Ireland as a result of his involvement in the Melbourne Football Club's international recruitment program (now known as the "Irish experiment").

Following his football career, Stynes focused on youth work, using his profile to launch The Reach Foundation, which he co-founded in 1994.

As a result of his work with young people in Victoria, he was named Victorian of the Year twice, in 2001 and 2003, and with the expanded profile of Reach nationally, awarded the Medal of the Order of Australia in 2007.

[10] Tall and slim, Stynes was selected, along with James Fahey, and brought to Victoria to undergo a crash course in Australian rules.

Later in 1987, Stynes was part of the senior side which won their last six matches of the home-and-away season to finish in 5th place and qualify for Melbourne's first finals series since 1964.

Stynes ran through the mark as the final siren sounded; it was an error which resulted in a 15-metre penalty and brought the Hawk forward within range.

Buckenara scored the goal, giving his team a two-point win and ending Melbourne's fairytale charge to the premiership (n.b.

He cemented his position in Melbourne's senior team in 1988 and drew praise for his consistent play and for his innate skills and ability.

He was installed as a hot favourite to win the Brownlow Medal after averaging an astounding 30.6 disposals and 11 marks per game over the final 8 rounds.

[citation needed] An exceptional run of consecutive games which had begun in Round 18 of 1987[13] almost ended with a severe rib injury in 1993 that Stynes sustained from a collision with teammate David Neitz in a match against the North Melbourne Football Club.

Despite being ruled out by medical officers for six weeks, he convinced his coach Neil Balme to pass him in the club fitness test and wore a chest guard in order to play the following Friday night.

[17] Stynes finished the season with his consecutive games record unblemished and achieved All-Australian selection for the second time.

[13] In 1994, he suffered a medial ligament tear but continued to play through it, going on to string together three fine seasons between 1995 and 1997 in which he won consecutive club champion awards.

[13] In 1994, Stynes co-founded (with film director Paul Currie)[20] The Reach Foundation and became a prominent youth worker in Victoria.

Shortly following his election, he declared his staunch stance against any proposed relocation of the club to the Gold Coast or elsewhere.

[26] In March 2011, Stynes met Prince William, Duke of Cambridge in Kerang, teaching him basic Australian rules football skills.

[30] In February 2012, Stynes stepped down from the presidency of Melbourne, citing a desire to devote his energies towards his family and wellbeing.

[32] In 2000, Stynes received an Australian Sports Medal[33] and was named in Melbourne Football Club's Team of the Century.

In 2001, he received the Centenary Medal "for establishing and leading a Reach organisation for youth development" and was named Victorian of the Year.

[39] Stynes intended to make clear that he was not stepping down from his role as President of the Melbourne Football Club but instead just taking a break to seek treatment.

[41] He continued to work during his treatment and participated in the filming of a television documentary about his life and his battle with cancer, Every Heart Beats True: The Jim Stynes Story, produced by friends Jules Lund and Reach co-founder Paul Currie which aired on 19 September 2010 on the Nine Network.

[50] Former teammate and captain Garry Lyon gave an emotional tribute to Stynes on The Footy Show, saying: "Jimmy refused to let the game define who he was.

[59] The Jim Stynes Foundation is a nonprofit founded in 2015 to "continue developing programs and initiatives that embody resilience, prioritizes mental health and shapes our future".

[61] The award is given at the ceremony for the Brownlow Medal, and it has been awarded to Daniel Jackson (2012), Zac Smith (2013), Beau Waters (2014), Dennis Armfield (2015), Jimmy Bartel (2016), Jack Hombsch (2017), Neville Jetta (2018), Stephen Coniglio (2019), Bachar Houli (2020), Travis Boak (2021), Joel Selwood (2022), and Sam Docherty (2023).