They were always good friends in any case since becoming teammates. McGregor joined Hibs the year after Gray and they enjoyed some extraordinary moments together, including the 2016 Scottish Cup final victory over Rangers. Indeed, McGregor, a Leither, was one of the first to jump on Gray’s back as he celebrated his late winner in the corner with fans.
They have also experienced the not so good moments. According to Gray, they became “gym buddies” for four months in 2019 after sustaining serious injuries – knee ligaments in Gray’s case, a hard-to-diagnose groin problem in McGregor’s – within a week of one another. It meant they missed the unravelling of Paul Heckingbottom’s short time in charge.
Another low point was last season’s Scottish Cup final defeat to St Johnstone, which they watched unfold in its grisly entirety from the bench. It’s where they spent a lot of that campaign, nearly always side by side. They sat next to one another on too many occasions for their liking as they toured round Scottish football grounds contemplating their own footballing mortality.
“The two older heads so we have probably got more in common,” explained McGregor, when asked about this seating arrangement, on subs’ benches from Pittodrie to Palmerston Park. “Two mid-30-year-olds."
There are no hard feelings between the pair and the recently departed Jack Ross, the manager responsible for this lack of match action. Gray, 33, took the somewhat extreme decision to retire at the end of last season after featuring just five times in his final campaign and having been invited by Ross to become first-team coach.
McGregor, meanwhile, made 15 appearances and at 35-years-old is still available for selection, including for this afternoon’s Premier Sports final against Celtic.
The difference is it’s Gray who’s making the decision about whether to play his pal or not. It’s reasonable to assume that McGregor won’t feature in the starting line-up, although in these current times, when a pandemic is again rife, there’s no guarantee who might run out of the tunnel at just before 3pm today.
McGregor dropped out of the squad all together for the midweek win over Dundee having started the 1-1 draw with St Mirren a few days earlier, with Hibs having been hit by suspensions to Paul Hanlon and Paul McGinn.
It’s a tough one for Gray, who will be aware McGregor missed out on St Mirren’s League Cup final win over Hearts in 2013 while rehabilitating from an ACL injury. Like Gray, McGregor was in the Hibs side beaten by a last-minute goal from Ross County’s Alex Schalk nine weeks before redemption was gained in epic fashion back at the same stadium against Rangers.
Gray knows he must put friendship aside. It is one of his first big decisions as caretaker manager and one of his last for the time being, with Shaun Maloney set to take charge next week.
Handing out cup final starting berths is a very serious business. It’s difficult enough before run-of-the-mill games.
“It is something new to me, something that I have never really done before and it is a challenge,” admitted Gray earlier this week at the Hibs training centre.
“As captain I have had conversations with players so that is not new. I know you are dealing with things in a different way now and being viewed in a different way, but I do think it helps that I have played in the same team and, obviously, worked with them in a coaching capacity over the last six months as well.”
McGregor hasn’t quite got used to using the term “gaffer” when conversing with Gray in training. “It's been such a quick turnaround, it's still Davie-boy,” he said. “I don't know if that's disrespectful, I might need to start calling him gaffer to have a better chance of getting involved in the final. I might start that today!”
Of course, Gray goes by another name when it comes to the fans in the stands.
"He'll just go up a couple of notches in everyone's estimation (if Hibs win),” suggested McGregor. “He's already Sir David, I don't know if there's anything above that…
“It's great for Davie, he's come in and it's been a seamless transition. I need to take my hat off to him. He just started coaching this year. He's come in and done all the team talks and he's got the respect straight off the bat, so it's great having Davie to lead us out.“I've been friends with David for a long while but I've been really impressed by how he has stepped up to the mark. His time will come but he will probably say himself that he's still learning although he's done really well so far.“The year we spent on the bench we got to know each other quite well,” he added. “We had a lot of long conservations. Davie was here the year before me and I played right centre-half and he played right-back for many a year so we've got that bond.
“I am just delighted for him. He's worked ever so hard in his playing career and he's transitioned into coaching. He took that big step, still being relatively young, and has taken it with both hands. Hopefully he succeeds.”