“It was probably for the best that I didn’t get on,” jokes Leeds United’s head coach. “What a striker Jimmy was – he had a hammer for a foot.”
Tomorrow, Monk will be in the opposite dugout to Hasselbaink at Queens Park Rangers in a game that marks the 37-year-old’s bow as United chief. It promises to be an intriguing insight into where the Yorkshire club are at following another busy summer at Elland Road, with seven new signings having arrived along with a new chief executive.
It is Monk, however, who most eyes will be on in the ‘High Noon’ showdown. He is the seventh head coach to work under Massimo Cellino in a little over two years and much is expected of someone who not so long ago was considered to be one of the Premier League’s brightest talents.
For his part, Monk is embracing the challenge after six months out of the game following last season’s dismissal by Swansea City.
“I refined a lot of things after leaving Swansea and decided how I would do things differently,” said the former defender when speaking to The Yorkshire Post. “I have been putting those thoughts into practice since coming to Leeds.
“I do feel that what we are giving these players and how I am as a manager are an improvement on my time at Swansea. It feels to be a better way of working.”
Under Monk, Swansea achieved their highest Premier League position of ninth.
Coming on the back of how he had transformed a team in a relegation scrap when he took over in February, 2014, into a comfortable mid-table finish three months later, it marked out Monk as a bright talent.
His sacking four months into last season, therefore, seemed harsh. Monk, though, was always keen to return to a job he had first considered more than a decade ago.
“Management was something I first knowingly wanted when I was 26 and had the serious injury,” said Monk, who missed almost the entire 2006-7 campaign with a cruciate ligament injury.
“I had always been an organiser, being captain and things like that. But it was only during the injury that I thought about what would happen after my career.
“Had I finished that day, I wouldn’t have had anything to fall back on. It panicked me a bit. Thankfully, I came back from the injury but, at the time, it was a worry.
“It was at that point I thought, ‘Football is what I know best and what I love, I have to start getting myself educated in the coaching side’.
“I did my badges while still playing and as I did those badges, I grew closer to the managers I played under. I got more of an insight into things.
“I would watch how a manager spoke to the lads, even if just a simple ‘hello’. What did he do in meetings? How they presented ideas. Plus, what they did at half-time and full-time.
“I was lucky enough that I had managers who were very open to me. They allowed me to have an input into what they did, allowing me to ask after training why we did certain things.
“Brendan Rodgers was probably the best in that respect. But Roberto (Martinez), Paolo Sousa, Michael Laudrup were all good to me.
“I also tried to remember what the managers had been like when I was younger. (Glenn) Hoddle, (Gordon) Strachan, Graeme Souness were at Southampton along with Dave Jones.”
Tomorrow will see Monk finally go head-to-head with former Leeds striker Hasselbaink. It is a tussle he is relishing.
“I have watched his career since moving into management,” he said. “You have to take your hat off to him. He seems a real thinker about the game and very astute.
“Jimmy did a great job at Burton and he is now at QPR, looking to do good things. He arrived midway through last season and has had that period to manoeuvre a few things.
“I am sure he will want to put his stamp on things, as we all do, QPR are a big club who have been in the Premier League recently.
“The pressure will be on Jimmy to get them promoted. But you don’t moan about it, you just fight to fulfil your ambitions.”