But as we approach the end of the season, the landscape has changed dramatically for the former Tottenham midfielder, and with the transfer window looming, he could face a big decision.
Having witnessed his stock plummet throughout 2016/17, the 23-year-old finds himself in a liminal space at Anfield.
Little more than a spare part, this will be a hugely important summer as Stewart shapes his future.
The Promise of 2016/17
Few players bookend their season’s preparations quite like Stewart did last summer, with the midfielder producing an exceptional performance in Liverpool‘s 4-0 win over Barcelona at Wembley.
In front of almost 90,000 supporters, Stewart replaced Philippe Coutinho at half-time to line up opposite the likes of Javier Mascherano, Sergio Busquets, Lionel Messi and Luis Suarez.
And despite coming up against a host of world football’s finest creative talents, there were little more memorable moments than Stewart robbing Busquets near the halfway line and threading the ball through for Divock Origi to make it 3-0.
The Liga giants were limp, lethargic and decidedly off their game, but it was a statement display from Stewart.
He also featured in the 5-0 win away to Burton Albion in the League Cup, before playing the full 90 minutes in the 2-1 victory at home to former side Spurs in the tournament’s fourth round.
What has transpired for the Enfield native, however, is far from that hopeful scenario.
A Wasted Season
That these are his only appearances of 2017 compound his increasingly peripheral role under Klopp, further magnified by his continued absence in the Premier League.
Remarkably, since September 16, when he played one minute in the 2-1 win away to Chelsea, Stewart has only featured in Klopp’s 18-man squad in the league on four occasions; each as an unused substitute.
Stewart has become surplus to requirements, instead turning out for the Reds’ U23s, of which he has started 15 of 32 competitive games this season, benefiting from the increased age bracket.
The only player over the age of 21 to play fewer senior minutes than Stewart (372) this season is Danny Ings (49), who has missed the last six months with injury.
There is little argument to suggest Stewart should be starting for Liverpool week in, week out, and his performance against Barcelona represents something of a bemusing anomaly.
But it is difficult to ignore the likelihood that, somewhere down the line, Stewart was sold a lie.
Speaking after the win over Spurs in the League Cup, for example, Klopp described Stewart as “the best challenger in the squad,” seemingly lying through his teeth when he proclaimed that “he is very important.”
Turning 24 in September, Stewart cannot be content with serving as a role model for Liverpool‘s more talented academy stars, turning out against the Reading U23s at Wycombe’s Adams Park.
What Next for Stewart?
They were said to value the midfielder at up to £12 million, placing a considerable valuation over the head of a player who, at that time, had played just 18 minutes of league football in five months—a tally he is yet to add to.
With six games left to play in 2016/17, and with Can returning to form and Grujic returning to fitness, there seems to be no way back into contention for Stewart.
This is particularly clear given Lucas has been preferred as cover for Henderson in the No. 6 role, and Stewart hasn’t even appeared on the substitutes’ bench since February’s 3-1 loss to Leicester City.
Having effectively wasted a season serving as a seventh-choice midfielder, he should be considering his options—despite the heartache of leaving his boyhood club.
Liverpool will be playing in Europe next season, and this will increase the need for depth in Klopp’s ranks, but it will also increase the need for quality, too.
For both parties, sealing a move away would be the best option, and for the club, they can hope to secure a similar deal to that of Brad Smith, who joined Bournemouth for £6 million last summer.
Incredibly, this would mean lowering their valuation, but for the sake of salvaging Stewart’s career, it is a necessary sacrifice.