On the back of eight defeats in their last nine games, the West Yorkshire club have slipped from third to eighth and now sit just four points above bottom-placed London Broncos.
Relegation is not being mentioned but, if this freefall continues, it is inevitable it will soon rear its ugly head on the agenda.
Still, with seven games remaining, Chester remains defiant that they will emerge unscathed and salvage something from what he concedes has probably been his most difficult campaign since taking over in 2016.
If you had asked him his thoughts last Friday, mind, after yet another derby defeat against Castleford Tigers, the answer may have been different.
Chester was as deflated as anyone in the aftermath of the 36-16 home loss.
Indeed, it was perhaps a wise option to send assistant Lee Gilmour into the post-match press conference; he may have said something he regretted.
However, one of the many beauties of sport, of course, is that generally you quickly get chance to have a go at it all again.
That is why Chester and his under-pressure Wakefield Trinity side will address tonight’s contest with renewed vigour, zest and, hopefully, a sharper edge; they frittered chances away against a Castleford Tigers side largely under the cosh until running away with things in the final quarter of the contest.
The 40-year-old said: “There’s pressure every week; I’m not going to say it’s a must-win game at Wigan.
“It’s important we improve in certain areas and I’m confident we can do a job on them on Thursday night.
“We deal with it (pressure) quite easily.
“We don’t look at the games coming up. We just deal with each week at a time.
“It’s more about the performance this week. If we can tidy a few areas up and make the most of the good ball we’re getting we’re a very hard team to beat ourselves.
“Defensively I thought that first 40 minutes we were really, really good against Cas. I thought we played well for 60 minutes but those two spells – 10 minutes at the start and end of the second half – cost us.
“I thought the difference between the two sides was they executed their plays.”
Wigan will give such profligacy short shrift, too; Adrian Lam’s side may have lost 32-10 in their own derby at leaders St Helens on Friday but that was on the back of a five-match winning run and they have certainly found their feet under the former Queensland State of Origin scrum-half.
“It was always going to take a bit of time with Lammy coming in,” said Chester, who played alongside the Papua New Guinea international at Wigan in 2001.
“There’s new structures and he wants to play a little different to how Waney (Shaun Wane) wanted them playing; they are a little more expansive now.
“They are playing well and are hard to beat on home turf.
“Saints certainly showed the way to beat them but we just have to match their physicality; they are a big side, and an aggressive team and we have to make sure we get out the blocks at them.”
Chester says he is likely to switch full-back Ryan Hampshire to wing in an enforced change.
Winger Mason Caton-Brown has dropped out after suffering some concussion symptoms following “a whack in the face” against Castleford.
Max Jowitt will come in at No1 for his first game since breaking a thumb with Hampshire – who started his career as a stand-off at Wigan – moving to the wing.
Jowitt has scored six tries in nine games for Trinity this term but has not played since the 25-18 Magic Weekend loss against Catalans Dragons on May 25.
Prop Craig Kopczak is out with a corked leg suffered against Castleford as Trinity continue to be hit by injuries although Danny Kirmond was training yesterday and should be fit in time for their next game at Saints on August 2.