Over the course of the next couple of weeks, the midfielder’s less-than-conventional career path could lead him to become only the fourth Scot to play for a Serie A club.
Henderson is currently undergoing a crash course in the wildly unpredictable world of Italian football. It is a country where the game has long been chequered by financial mismanagement and match-fixing scandals.
Controversy is seldom absent from the front pages of the daily sports papers in a land where football is king and, over the past few days, it is Serie B which has been making the headlines.
Bari, the club Henderson joined from Celtic in January, found themselves facing a tribunal last Friday over irregularities in their payments to players. The outcome was a two-point deduction which had significant consequences for Bari’s promotion hopes.
The decision, which is subject to an appeal this week, means Bari slipped from sixth to seventh place in the final Serie B table. They also lose home advantage in the single-match quarter-final of the promotion play-offs, which had to be put back a week because of the charges against them, having already sold 8000 tickets for the originally scheduled fixture.
Bari must now travel to play Citadella this Sunday in the quarter-final, hoping to reach the two-legged semi-finals on 6 and 10 June, with the dates for the play-off final matches now set for 13 and 16 June.
The chaotic end to a dramatic Serie B campaign has not only forced Henderson and his team-mates to revise their holiday dates, it has placed on hold a possible bid for the 22-year-old from Parma.
One of the stellar names in Italian football back in the 1990s, when they won three major European trophies, Parma have just completed a remarkable recovery from their most recent financial calamity.
Having previously emerged from administration caused in 2004 by the collapse of their owners, dairy firm Parmalat, they were declared insolvent again in 2015 and found themselves having to regroup in the fourth tier of Italian football.
They have now clinched three consecutive promotions, their second-place finish in Serie B this season helped by a 1-0 win over Henderson’s Bari in the penultimate fixture of the regular season.
Henderson impressed the Parma coaching staff that day and is said to be high on their shopping list ahead of their return to Serie A next season. Bankrolled by Chinese businessman Jiang Lizhang, who bought a 60 per cent stake in the club last year, Parma are eager to reclaim former glories.
Among the other players linked with summer moves to the Ennio Tardini Stadium is Mario Balotelli, pictured,the gifted but volatile striker who is out of contract at Nice. The prospect of lining up alongside Balotelli is another intriguing and unlikely twist in Henderson’s football tale.
Since making his debut for Celtic as a 17-year-old under Neil Lennon, he never allowed himself to simply be content at making up the numbers as a squad player with the Scottish champions, which can be the easy option for so many.
Henderson does have memories to cherish from his time at Celtic, including scoring his first goal for the club on the night they clinched the league title in 2014 with a 5-1 win over Partick Thistle at Firhill.
But, when it became clear regular first-team football would not be coming his way, first under Ronny Deila and then Brendan Rodgers, Henderson wasn’t prepared to let the grass grow under his feet.
He first underlined his outward-looking approach to life when he moved to Norway for a loan spell with Rosenborg in 2015, thriving at the Trondheim club and helping them win their domestic title that year.
The following season, he committed himself to a season-long loan at Hibernian where he quickly became a favourite of the Easter Road faithful and ensured himself of a lifelong place in the club’s folklore as an influential member of the 2016 Scottish Cup winning side.
Henderson looked well equipped at that stage to make progress on his return to Celtic but he made only six starting appearances for Rodgers’ “Invincibles” in 2016-17, then dropped further down the midfield pecking order at the club following the arrival last summer of Olivier Ntcham.
His only appearance for Celtic in the season just ended came as a 67th minute substitute in a 1-0 win over Dundee last October. The writing was on the wall for Henderson’s career at his boyhood club and he wasn’t about to bury his head in the sand and ignore the message Rodgers was sending.
His January move to Bari, for a fee in the region of only £100,000, came out of left field but Henderson has made a hugely positive impression at a club still emerging from their own financial difficulties as they pursue a return to Serie A for the first time since 2011.
He has scored twice in 18 appearances for the side coached by Fabio Grosso, the former Inter Milan and Juventus defender who scored the decisive penalty for Italy in their 2006 World Cup final shootout triumph against France.
Bari will certainly look to retain the services of Henderson, under contract with them until 2020, if they successfully negotiate the promotion play-offs over the next couple of weeks. One way or another, he is poised to join the illustrious trio of Denis Law, Joe Jordan and Graeme Souness on the short list of Scots to play in Serie A.