Brian McClennan, Matthew Elliott, Andrew McFadden and Stephen Kearney all arrived with high hopes and big plans which never quite eventuated, for differing reasons along the same theme.
Nathan Brown had almost two decades of high level coaching experience behind him but couldn't find the answer, leaving the team in a worse position than he found it, while the interim role has been a chastening experience for club legend Stacey Jones, with Friday's 48-4 pasting in Townsville continuing a sequence of heavy defeats.
In that context, you have to admire Webster's conviction to take on the role, given he has never been an NRL head coach before, which feels a bit like learning to swim in Cook Strait.
"[No] rookie coach is going to be handed a dream job," Webster tells the Herald on Sunday, in his first interview since being announced as the new coach in July. "Any rookie coach is going to be handed a challenge."
But it's something that Webster is enthusiastic about, rather than daunted by. And where other might see problems, puzzles and purgatory, he sees potential and promise.
"If you hadn't spent time at the Warriors and you don't know what the bones of the place are, and the strong foundations that are actually in place – though they don't probably come out on the field all the time at the moment - then I can understand maybe you might be worried," says Webster.
"But if you've been there, loved it and invested in it like I have it's something that you're really excited about."
Webster spent two years as an assistant coach at the Warriors under McFadden in 2015 and 2016, a life experience that left a deep impression.
Subsequent assistant roles at the Tigers and Panthers followed, but Webster retained a soft spot for the Auckland club.
So when the job became available, he jumped.
"I always followed the Warriors," said Webster. "I was pretty passionate about the place - I enjoyed my time there so much. It was always in the back of the mind but obviously being an assistant coach, you're always really focused on what's happening right now."
The 40-year-old has been coaching since his early 20s, including six years in England.
He impressed during his Warriors stint, understands the league landscape here and has been a crucial part of the Penrith machine over the last two seasons.
He is seen as a man on the rise, but moving from an assistant role is always a big leap to make, as history shows there aren't too many second chances in the NRL.
"I felt like if I waited another two years I'd be two years more ready, in 10 years I would be 10 years more ready," says Webster. "So when's the perfect time? The perfect time is when you feel passionate about something, when you know that you can actually have an impact."
Webster sensed that with the Warriors – something he says he may not have felt with another club - though it wasn't a decision he took lightly.
"I asked a lot of advice," says Webster. "My family, friends and people who were in the game. I laid all the cards on the table."
The Warriors finished 12th last year, with an 8-16 record (only four previous seasons had been worse). They currently sit 14th, with two rounds to go, after just six victories in 2022.
They have the worst defensive record in the NRL, conceding an average of 28 points a game, and have won just two games since May.
It looks like a big transformation job but Webster doesn't see it that way.
He feels the club has "really strong bones" and the experiences of the last three seasons marooned in Australia has built resilience that will manifest in the future.
Relocating home next year will provide a massive boost, along with the opportunity to revive the development teams and pathways system.
But ultimately, it will all come down to the playing group.
Webster is happy with the roster – "the current retention has been really good" – and the new arrivals, headed by Marata Niukore, Mitch Barnett, Te Maire Martin and Charnze Nicoll-Klokstad.
"The experience and resilience that the club has recruited can add an extra layer," says Webster. "You always think it's further away than it actually is but our big thing is to make sure these new recruits gel with what's already in place.
"The retention has been excellent, but we can get them even better. And we can really reveal some stars, some young kids. We've got to take that challenge too, to unearth them."
Webster also ruled out the possibility of luring some Penrith players to Auckland, with a few big names off contract.
"No - I won't be going down that path," says Webster.
But the Warriors faithful will hope he brings other ingredients from the Panthers, specifically the modus operandi of Ivan Cleary.
Webster also worked with Cleary at the Tigers and doesn't hide his admiration for the former Warriors mentor who has transformed Penrith, largely off the back of homegrown talent.
"Ivan really shows his belief in his players and his staff," says Webster. "He gives people a job and he trusts them. You don't really have earn that trust; you get it straight away until proven otherwise. That style creates a lot of belief and confidence in everyone.
"Players want to work hard for him and for each other. And they actually feel like they belong to the place and they can actually have a real impact."
When the Warriors offer materialised, Webster didn't hesitate about having a conversation with his boss.
"I was open and honest with him," said Webster. "I was really lucky to get that opportunity to talk to him and seek advice. His exact words were [he'd be] disappointed to lose me but if I went, I'd go with his blessing."
Cleary will continue to be a mentor next year – despite being a competitor – while Webster will also lean on his coaching staff and McFadden, who is returning in a general manager role.
"It was really important that I just didn't put a group of yes men around me," says Webster.
Webster will arrive in Auckland in mid-October, planning to live in an apartment for a few months before finding somewhere more permanent.
He emphasises that once pre-season gets underway, there needs to be a fresh start, without forgetting recent lessons.
"It's really important for us to have any sense of improvement that we're going to know where we've come from," explains Webster. "But we've also got to understand that it's a new squad. So digging up old memories, good or bad ones, might not resonate with that."
Decisions around captaincy and other roles will be made in due course but Webster is full of admiration for the job that incumbent Tohu Harris has done and indicated it would be "his to lose".
While Webster has yet to put on his Warriors tracksuit, he already has ideas about the brand of football he wants to see.
"The biggest thing is, I hope the fans go home and they've seen a really resilient group," says Webster.
"A team that can attack from anywhere but they can stand up under pressure; it's not an attack that's got heaps of errors and it's not reliable.
"And if the shit hits the fan, we can defend our own try line, we can turn them away and we can show that resilience for our supporters. So they walk away really proud that they've got an exciting, skilful team, but a team that's willing to stand and fight for each other."