The Cheltenham Gold Cup is the pinnacle of National Hunt racing, but it is perhaps unfair to let two Fridays in March, six years apart, define the career of Paddy Brennan.

Brennan hit the ultimate height in 2010 when Imperial Commander took advantage of the fall of Kauto Star to storm up the Cheltenham hill and beat off the other Ditcheat legend of the era, Denman.

However, the fences got their own back in 2016 when Brennan and the smooth-travelling Cue Card came to grief as a mouthwatering battle with Don Cossack was about to come to a head.

It was also at that obstacle where Cue Card was to fall in his final appearance in the Gold Cup in 2017, but 2016 was the year the nose-banded Colin Tizzard superstar was primed to a peak.

Brennan has ridden over 1,500 winners over jumps and has been in the weighing room for nearly a quarter of a century.

One of the characters among the riding fraternity, he cut his teeth at the cut-throat finishing school of Jim Bolger. And it was a case of out of the frying pan and into the fire when moving to the UK at the turn of the century, joining Paul Nicholls as a conditional.

His time at Ditcheat was followed by a move to Philip Hobbs, where he rode as second jockey to Richard Johnson and was champion conditional in 2004/05.

It was during that season that Brennan recorded his first Grade One success when partnering Kevin Bishop’s Ashley Brook to a 16-length romp over War Of Attrition in Aintree’s Maghull Novices’ Chase.

Before triumphing at Aintree, the duo had finished second in the Arkle at Cheltenham and it was a further 12 months before the Irishman broke his duck at racing’s Olympics when landing the Fred Winter with 40-1 shot Shamayoun.

A move up north to become Howard Johnson’s stable jockey brought further Festival glory in 2007 when Inglis Drever won the second of three World Hurdles in the gold and black silks of Graham and Andrea Wylie.

Brennan’s time trawling the northern circuit was brief, as he was cut adrift by Johnson after one season with the County Durham handler.

But a safety net was provided by Nigel Twiston-Davies and so began a four-year partnership that would take both men to the very top of the sport.

He passed 100 winners in a season during his first campaign as the Twiston-Davies number one – but the Brennan era at Naunton Downs will forever be associated with Imperial Commander.

They first hit the headlines when landing a gamble in the Paddy Power Gold Cup at Cheltenham and in the spring an inspired Brennan produced a majestic ride as Imperial Commander claimed the scalp of Voy Por Ustedes in the Ryanair.

That signalled a Gold Cup mission for the 2009-10 season and the first stopping point on the journey back to Cheltenham was Haydock, where Ruby Walsh picked Brennan’s pocket in the dying strides on Kauto Star to prevail by a nose.

Back at his favourite course at Cheltenham in March and with Kauto Star struggling when falling, Brennan and Imperial Commander stormed up the Cheltenham hill for a second successive Festival win – and this time in the blue riband itself.

Imperial Commander’s Gold Cup was leg one of a memorable treble for the Twiston-Davies team on the final day of the 2010 Festival and Brennan brought up his own Gold Cup day double when his beloved Pigeon Island landed the Grand Annual that drew the action to a close.

Around this time, Brennan was also forging a partnership with Tom George’s bold front-running grey Nacarat. The pair combined twice for big-race success, with their finest hour coming when making all to win the Bowl at Aintree’s Grand National meeting in 2011.

The emergence of Twiston-Davies’ son Sam as one of the weighing room’s hottest prospects saw Brennan jump before he was potentially pushed in April 2011, although the handler was said to be shocked by the decision.

Although he was never far away from Naunton Downs, as he helped Fergal O’Brien set up his fledgling base on the same gallops used by his former employer, Brennan spent four years in the big-race wilderness before being handed the call-up to ride Cue Card by Colin Tizzard.

Despite the earlier mentioned lows in the big one, there were plenty of highs, with the dynamic duo linking up for victory six times from the 15 occasions they were united on course.

Taking over from Daryl Jacob at the start of the 2015-16 season, Brennan and Cue Card got off to the perfect start when winning Weatherby’s Charlie Hall Chase.

Cue Card then went on to claim the second of three Betfair Chase wins at Haydock before the duo made it a hat-trick of victories when an inspired Brennan hauled Cue Card home to down Vautour in the King George – a triumph that was to be the combination’s finest hour and one of the rider’s most notable achievements in the saddle.

A decisive victory in the Aintree Bowl in 2016 offered some consolation to their Gold Cup despair, as the pair continued to pick up Grade One staying chases – including another Betfair Chase in November of that year and an Ascot Chase in February 2017.

The upward curve of the O’Brien stable has seen Brennan make regular appearances in the winner’s enclosure during the latter stages of his career and a further Grade One was added to the CV when he drove home Poetic Rhythm for his great ally in the 2017 Challow Hurdle.

However, that was the last top-table success for five years until the battle-hardened juvenile Knight Salute took the Irishman back into the limelight at Aintree in April 2022.

Initially, Knight Salute had dead-heated with Gordon Elliott’s Pied Piper following a thrilling finish, but was then awarded first place outright in the stewards’ room, despite Brennan’s protestations that there was no case for Davy Russell aboard Pied Piper to answer.

That sportsmanship has been the hallmark of Brennan’s latter years in the saddle, along with a steadfast loyalty to both his colleagues in the weighing room and trainer O’Brien.

Scriptwriter followed in Knight Salute’s footsteps with a Triumph trial success and Dysart Enos ensured Brennan remained a big-race player right until the very end of his decorated career when landing the Grade Two bumper at Aintree in 2023, before making a successful switch to novice hurdling.

O’Brien’s Kamsinas was another late Grade Two victor for Brennan at Haydock last November and the jockey reached 1,500 winners on Teorie at Catterick the following month, having passed the 1,000 milestone just over seven years earlier.

There was to be no fairytale final success at the Cheltenham Festival last month, but Brennan fittingly bowed out at the home of National Hunt racing a month later aboard the O’Brien-trained and aptly-named Manothepeople.