On a dark Sunday evening in November 2020, the day after Ireland had lost to England at Twickenham in the Autumn Nations Cup, Leinster hosted Cardiff at an empty RDS in the Pro14. Rugby was keeping the show on the road but there wasn’t much to illuminate the gloom. Not until the 15th minute anyway.
Leading 7-0, Leinster moved the ball from a line-out on the right across the pitch to fullback Jimmy O'Brien, hugging the left touchline on his own 10 metre line. In what seemed the blink of any eye he raced over half-way, expertly chipped Blues fullback Matthew Morgan and turned a 40-60 chase for the bouncing ball with the covering Jason Tovey into a try when plucking the ball from the latter's grasp to run on and score.
That opportunist try, in just his 16th Leinster start, showcased his awareness of space, speed, footballing ability and trusty left boot. It was four days shy of his 24th birthday. He’d only made his debut two years previously to the day, but after that night it was no surprise when O’Brien made European debut the following month in Montpellier.
O’Brien capped a fine performance with the counter-attack which led to Montpellier crosskicking in their own 22 before he latched onto Robbie Henshaw’s tap down to score in the last minute.
James Lowe's injury helped to open the door for O'Brien to start on the left wing against Montpellier this season, when scoring one try, and that memorable four-timer in Bath a week later. Then, with Jordan Larmour sidelined for the two games against Connacht, O'Brien started both legs of the last-16 tie on the right wing. But in Saturday's quarter-final O'Brien is clearly there on merit.
O'Brien's career trajectory mirrors that of Hugo Keenan, who is only five months older. Alongside Keenan, O'Brien took a detour with the Ireland Sevens in 2017 and 2018. It's a measure of his versatility than in his 38 starts so far for Leinster, 20 have been at fullback, ten at outside centre, five on the left wing and three on the right. There have been brief cameos at nine and '10' too.
Indeed, starting out, he’d initially been a scrumhalf in Newbridge College before moving to outhalf.
"I was coaching the second years when he was up playing with the Juniors," recalls Dave Brew, a coach through O'Brien's school years. "He was playing a bit of scrumhalf with them and then I had as a Junior Cup player the following year.
"The first thing I'd say about him is the difference Jimmy and another lad, Jake Howlett, who was also interprovincial standard, made. Jimmy was a real standard-setter. Training didn't become more strict, just that he set the bar. Players thought: 'Oh My God, this is what we need to be doing'. Not that he led from the front intentionally, but his individual skill set was exceptional at that level. He was one of those guys who always looked like he had more time on the ball and yet he played the game at a tremendous pace.
“Whenever he was executing a play, both the standard and the pace it was done at was a little bit ahead of his years.”
Minis
His mum and dad, Caroline and John, hailed from non-rugby territory in Clonmel, although as his dad was a long jumper and sprinter. Then, on moving to Kildare, their uncle Toby Sheridan persuaded his parents to let his older brother Patrick and O'Brien, who is the middle child of five, to try mini rugby at Naas RFC.
Like Tadhg Beirne, O'Brien is from Eadestown, as is Connacht's Diarmuid Kilgallen and Rowan Osborne, and their footballing skills were undoubtedly honed by playing GAA in their formative years.
Geordan Murphy having been something of a trailblazer at Newbridge College and Naas RFC, like O'Brien and Osborne, James Tracy, Jamie Osborne (no relation) and Adam Byrne all played in Naas as well.
By contrast his older brother was an aggressive flanker who played on the Newbridge senior cup team and the Naas Under-20s. Defensive instinct runs in the family then, as sriking as the four tries against Bath was O’Brien’s tackling.
“He’s an excellent defender as well,” says Brew. “He really rushed and harried from ‘10’ and at that level you get junior and senior schools teams who have a big number eight who try to run over the ‘10’ and that certainly wasn’t a problem for us that year.
Quick too, especially over the first five metres. “But if he did make a break he generally had the pace to finish it off.”
With O'Brien at outhalf, Newbridge reached their second Leinster Schools Junior Cup final in 56 years, losing 10-5 to a St Michael's side captained by James Ryan.
O'Brien took a break from Schools Cup rugby in his transition year before helping Newbridge to a senior cup semi-final, where they lost to a Blackrock team containing Joey Carbery, Hugo Keenan, Nick Timoney, Conor Oliver and Jeremy Loughman.
The following year O’Brien was more often used at ‘12’, “to free him up and let him express himself a little bit more.”
O'Brien guided Newbridge to the Leinster league title when beating Roscrea in the final before drawing with them in the cup semi-final and losing the replay by a point, as Roscrea went on to lift the trophy.
“He was the true leader of that team. He really bought into the ethic that it was a squad effort. He had a very mature attitude. Through school he was quite strong academically. A very confident young man. He’s definitely a guy that progress is key to him. You see that with the career he’s had.”
A graduate of financial mathematics in UCD, O'Brien was mostly used as a replacement by the Ireland Under-20s in the 2016 Six Nations and World Cup.
It is a matter of opinion as to what degree his segue with the Ireland Sevens further honed his ball playing skills or delayed his pathway into the Leinster squad.
In any event, as a versatile footballer O'Brien seems almost the prototype of the roaming modern-day back being honed by Stuart Lancaster. Employed in a multitude of ways, be it playmaking, kicking or finishing, he rarely makes a mistake.
Consistency
Back in February, Lancaster said of O’Brien: “Consistently good would be the phrase I would use. He is consistently good. He is not just consistent.
“In terms of multi-positional, he is the classic multi-positional outside back. I do run him at ‘10’. I would be happy to play him at 12 or 13. He has played on the wing and obviously he is excellent at 15 as well.
“So, he has got the ability to be a very good all-round footballer. He has obviously got his left boot, he’s fast - he has got proper top end speed and he’s good speed endurance as well. He’s a bit like Hugo.
“You put that package together, bravery, intelligence, confidence now that has grown over the course of the last three or four years that I coached him.
"He used to be quite quiet and it's quite a hard place to come into, Leinster, if you're a young player trying to make a mark. Gradually, a bit like Ciarán Frawley, Hugo, these backs have started to come through and prove themselves initially from the bench, then into the PRO14, then onto the bench in Europe, he plays well in Europe and now he is very much a trusted member of the senior squad."
As to what is O’Brien’s best position, even Lancaster doesn’t seem entirely sure.
"Eh, '15'. But I'd say the same about Hugo (Keenan) as well to be honest. The advantage with Jimmy is that when you play Jimmy and Hugo together you can almost interchange them anyway. I think Hugo is often very good in the air and with his kick-chase, Jimmy's left foot on an exit works well, but equally if Garry Ringrose wasn't available and we needed to play someone at '13' I'd be very happy with Jimmy at '13' as well.
“I think generally towards the outside of the backs would be my preference really but he’s multi-positional. Because he’s a good ball player as well you could slot him in at ‘10’. He has that level of organisation off the ball and that ability to play out the line.
“It’s a good problem to have, but I never really see it as a problem because that sort of multi-positional way we play anyway. You look at the way we attack. There’s often different people taking the job at first receiver, different people out the back of shapes, it’s less traditional than you would probably see.”
Called into the Irish squad during the Six Nations, he is clearly on Andy Farrell’s radar and while the outside backs has become an even more competitive area with the emergence of Mack Hansen, a place in the 40-plus squad for the five-game tour to New Zealand is conceivable.
As Brew simply puts it, on behalf of a club and a school and a county:
“It would be great to see him in green at some stage.”