He will lead his side out at Wembley tomorrow heartened by the support of arguably the club’s most famous son – Roger Millward.
The former Great Britain captain, who was player-coach when the Robins won their only Challenge Cup in 1980 and featured with them more than 400 times, congratulated the rookie for plotting a path to the showpiece event.
Chester, the 36-year-old in his first full season in charge, explained: “It was a card after the semi-final – a well done and good luck card.
“It’s great someone of Roger Millward’s stature sent the boys that.
“He was a massive part of this club in the 80s and is still about, always hanging around, and the boys are really proud to get something from Roger.
“What a great fella he is. I had the opportunity to sit with him at the end of last season at the awards night and he is still red and white through and through…”
The iconic black and white image of Millward raising the Cup 35 years ago, having played on against fierce rivals Hull despite breaking his jaw for a third time in just a few months, is something Chester would love to see joined by a colour version of current captain Tyrone McCarthy tomorrow.
“It would certainly be nice,” he said, ahead of the game with holders and Super League leaders Leeds Rhinos.
“There’s been a little bit of doom and gloom since that day.
“Rovers reached a final in ‘86 and got beaten by Cas’ but we want to go and win it.
“We’ve put ourselves in a real good position now and it’s whoever turns up on the day.
“We’ve just got to make sure that that team’s us this week.”
Chester invited three of the ‘80 heroes to speak to the squad before they embarked on this year’s Cup run – Phil Lowe, Mike Smith and John Millington.
He said: “They brought some old newspapers and gave a talk to the boys on what it meant to them as local kids to win the trophy.
“They spoke about the build-up and their feeling going into what is the best competition in this sport.
“And I definitely do feel this is still the best, better than the Grand Final.
“There’s a lot of tradition, a lot of good teams who have won this Challenge Cup.
“My first memories of it were in 1989 watching Wigan beat St Helens 27-0 and Gary Connolly got taught a bit of a lesson there at full-back.
“It’s a competition which we’ve wanted to do well in. We spoke in pre-season about the goals we wanted to set and reaching the semi-final was one of them.
“We’ve surpassed that now and now we want to go win it.
“We’ve been pretty good in one-off games so we’ll go there in confidence on the back of four really good victories and who knows?”
Rovers, who are under the threat of relegation having finished tenth and being sucked into the Qualifiers, are understandably massive underdogs given the class, experience and form of tomorrow’s opponents.
However, Rovers have won all three Qualifiers games so far after their epic semi-final win over Warrington and so enter the showpiece event in positive mood.
Nevertheless, Chester believes if his side prospers it will be an even bigger shock than when Hull FC, with him coming off the bench, dramatically defeated Leeds at Cardiff’s Millennium Stadium in 2005.
“We’ve certainly had a tough run this year,” he added.
“We’ve been away at Bradford and at Wigan, and had really tough quality opposition so there is some similarities to ‘05.
“We had Super League opposition all the way through back then but we’re looking forward to it.
“It’s been a hell of a journey and we don’t really want it to end.
“We want to give a good account of ourselves on Saturday and there’s a lot of belief and spirit in this group of players.
“I know on our day we can upset a lot of teams – as we have done this year.”
The majority of his squad have never played at Wembley so there is always the fear that the East Yorkshire club may freeze on the big stage.
But Chester – who will be hoping star scrum-half Albert Kelly passes his fitness test during their training session at Wembley this afternoon – intends to keep everything as normal as possible before 3.15pm arrives tomorrow.
“We want to try keep the boys as calm and relaxed as we can,” added the former Halifax and Wigan loose forward, who played for Rovers before injury forced his early retirement in 2008.
“I want it to just be this group of players and the rest of the staff on the evening before the final.
“I’m sure it will be an emotional meeting on Friday night but we want to try and keep everything as normal as possible leading up to the game in terms of training and what we do afterwards.
“We’re going to enjoy it. It’s my first time at this new Wembley stadium so I will enjoy it, too.”
Finally, what will be the last thing he tells his charges before they head out for what is, for many, the biggest game of their lives so far?
“Just that: to enjoy it and don’t let the game pass you by,” said Wakefield-born Chester.
“These moments don’t come along too often.
“I was fortunate enough to play in three finals – a Challenge Cup and two Grand Finals – and I’d give anything to go back to those kind of days.
“You are a long time retired and we just have to make the most of what is a fine occasion.
“Going down there is a great reward for the fans and people like (chairman) Neil Hudgell and (vice-chairman) Rob Crossland who have not just invested money, but time as well, into turning this great club around.
“We need to give a good account of ourselves. And I’m sure we will.”