He’s a Premiership-winning Captain, an icon of the Roosters and a legendary figure in NSW and Australian Rugby League.
With countless moments at the helm from his Roosters debut to his final match of first grade, we’ve compiled a list of the top five Brad Fittler moments, in chronological order.
Freddy’s First in Red, White and Blue – Round 1, 1996 vs Sydney Tigers
There was an air of excitement around Moore Park when the Club secured the services of 23-year-old Fittler, and the Australian Captain did not disappoint in his first match for the Club.
Coming up against the Sydney Tigers at the Sydney Football Stadium in the first match of the 1996 ARL season, the Roosters overcame a slow start to blow away their opponents and claim a 38-10 victory.
Brad Fittler Scores his First Try for the Roosters
Fittler's touch saw Andrew Walker dabble in a kick for Peter Clarke to score, before the man himself touched down for his first four-pointer in Red, White and Blue in the 77th minute after spinning out of a tackle close to the line.
He wasn't finished there though, slinging a bullet pass across field resulting in Clarke's second for the day, capping off his first match for the Roosters in style.
The Intercept – Preliminary Final, 2000 vs Newcastle Knights
Whenever Brad Fittler and Andrew Johns came together, you knew it was going to be a contest of epic proportions - and the 2000 Preliminary Final was exactly that.
With Fittler now the Club's Captain and looking to guide his side to their first Grand Final in two decades, in their way stood Johns and the Knights at the Sydney Football Stadium.
Match Highlights: Roosters vs Knights Preliminary Final 2000
It wasn't the start the men from Bondi were expecting as the visitors flexed their muscles to a 16-2 lead at the break, with a Craig Fitzgibbon penalty goal providing the only points.
An almighty halftime rev-up from Fittler kicked his side into gear as they headed back onto the turf, with the skipper combining with fullback Luke Phillips to send Anthony Minichiello over.
But it was Fittler who stole the show just minutes later, swooping on a cutout pass from Johns to streak away and score a famous try, springboarding his side to a 26-20 victory and an emphatic Grand Final appearance.
A Courageous Captain’s Knock – Grand Final, 2002 vs New Zealand Warriors
On the greatest stage, the greatest players stand up and etch themselves into folklore, and the 2002 NRL Grand Final is arguably one of Fittler's greatest of all.
Leading his side out to Stadium Australia against the New Zealand Warriors in search of breaking a 27-year drought, Fittler played a major part in the 30-8 victory, with many pundits believing he was worthy of the Clive Chuchill Medal.
2002 Grand Final Highlights: Roosters vs Warriors
Trailing by two points with 25 minutes remaining, Fittler showed composure to boot a 40/20, before sending over halves partner Craig Wing over to get the Roosters back in front.
After being the target of a savage barrage of hits from the Warriors' forward pack, Fittler courageously marched on despite claret cascading down the side of his face, and soon enough his boot produced more points to ice the result.
The battered and bruised Fittler was then immortalised with his arms raised in the air with the result sealed, before lifting the Club's 12th Premiership trophy aloft.
2002 Premiers | 20th Anniversary Part 4: The Grand Final
Age Shall Not Weary Him – ANZAC Day, 2004 vs St George Illawarra Dragons
The general consensus among Rugby League players is that by the time you reach your 30s, you're past your best - but that doesn't apply when you're Brad Fittler.
Just months after his 30th birthday, Freddy showed the NRL that he still had it and then some with his brilliant individual four-pointer on ANZAC Day in 2004.
Age Shall Not Weary Them: Freddy's ANZAC Day Try
Following a low-scoring and closely-fought affair in the third edition of the ANZAC Day Cup fixture against the St George Illawarra Dragons, the Red, White and Blue found themselves trailing 8-2 with 20 minutes left on the clock.
Enter the veteran Fittler.
Leading from the front, Fittler burst through the tiring defensive line, before producing a trademark left step on the fullback to touch down under the posts, with the solid out Sydney Football Stadium crowd in raptures.
Even commentator Ray Warren couldn't hold his composure in the moment, famously calling: "Well age shall not weary them! Freddy Fittler scores on ANZAC Day!".
Hobbled by pain and stress, he could still turn games with his passion and courage and toughness and desire.
Phil Gould Former Roosters Coach
The Final Outing – Grand Final, 2004 vs Canterbury-Bankstown Bulldogs
The 2004 NRL Grand Final not only marked a third-straight decider for the Roosters but the final game of top-level Rugby League for Brad Fittler.
A glittering career came to a close from the man who captained at club, state and international level with distinction, retiring as the most-capped skipper in Roosters history with a Premiership to his name.
And while the end result wasn't what he was hoping for, the stoic Captain provided the Roosters' first points of the match in a way no other could.
Famous Grand Final Tries: Fittler's Banana Kick
Just over ten minutes into this contest between two colossal sides, Fittler took the reins 20 metres from the line, executing a pinpoint kick from the outside of his boot under the posts, which saw winger Chris Walker pounce to open the scoring.
It was a moment that will forever be etched as the final try assist from Fittler, one that epitomised his confidence, finesse and ability.
Bonus Entry: Vintage Fittler – Auckland Nines, 2014 vs Brisbane Broncos
You knew we couldn’t leave this one off the list.
Ten years after hanging up the boots, Fittler made a famous comeback in the Tricolours for the 2014 Auckland Nines alongside a number of fan favourites who returned to the field for the pre-season tournament.
Auckland Nines 2014 Highlights: Roosters vs Broncos
Despite being 42 years young, the Club legend took his opportunity to recapture his glory days with both hands in the side’s second match against the Brisbane Broncos.
As the opposition shifted the ball out wide, Fittler wound back the clock as he took an intercept, streaking away 65 metres to score the most memorable try of the tournament with the Eden Park crowd in full support.