“The most expensively assembled team in history playing against a League Two side that relies on free transfers and loans,” the Wimbledon boss tells Standard Sport.
That assessment does not particularly inspire confidence that a Carabao Cup upset is on the cards at Stamford Bridge, but it is hard to escape the gulf in financial might between the clubs.
This second-round clash comes two days before transfer deadline day, by which point Chelsea might have crossed the £1billion mark in signings since the club’s takeover a year ago. Wimbledon have brought in 10 new faces this summer without spending a penny on transfer fees.
“It’s crazy when you look at the numbers and Chelsea’s spending in the last few windows,” Jackson says. “It’s a world away, like two different sports, but that’s the beauty of cup competitions.”
Wimbledon can reflect on their own world with satisfaction after the opening month of the campaign. They sit fifth in League Two, knocked Championship side Coventry out of the Carabao Cup and are unbeaten across all competitions. It is a fairly remarkable turnaround for a club that won only two of their last 23 league matches at the end of last season, but Jackson was always confident that slump would be halted with an active summer window.
“There was no hangover, because it’s a new team,” he says. “I was really keen to have that freshness, we needed to put last season to bed and look forward. We’re a different outfit now, we’ve recruited well. We needed a few leaders in the group and more experience, and we’ve got that.”
As well as a squad overhaul, changes have been made behind the scenes, too. Bobby Bacic has arrived as the new head physio and tweaks have been made after analysis into training loads.
“We had horrendous injuries at the end of last season, we were threadbare,” Jackson explains. “We had a deep dive into a lot of things. It took a lot of hard work and a lot of soul searching, but we’re really pleased with the transformation we have made.”
Jackson is grateful that he is the one in the Wimbledon dugout leading a new-look side, keeping his job amid last season’s struggles.
“You can have all the injuries in the world, but people still judge you on results,” he admits. “In the circumstances, I’m sure that certain boards would have made different decisions. But the club stuck with me and supported me all the way. That never wavered. That’s lovely as a manager, because you don’t always get that.”
Facing Chelsea will be the “biggest occasion” of Jackson’s managerial career to date, but Wimbledon will not be turning up simply to enjoy the Stamford Bridge stage.
“We’re not interested in the experience or the day out,” he says. “It’s brilliant for the supporters to go to Stamford Bridge, but we want to go there and win. I’ve been hammering that into the players.”
Jackson was in attendance on Friday night as Chelsea beat Luton for their first win of the season and was impressed with what he saw, though he admits predicting the side Mauricio Pochettino will name is an impossible task. His focus, instead, is on ensuring his players are ready to take advantage of any complacency from the hosts.
“We’ll give it a right go,” Jackson insists. “Our style will give us moments against anyone. If they’re not quite at it, we can exploit that. If they turn up at their level, it’s going to be really difficult for us to pull anything off.”
A lot of my pals are Chelsea fans and they’ll be in the crowd.
It will not be long after the full-time whistle before Jackson’s attention turns to Saturday’s trip to Newport, but will there be time for a post-match drink with Pochettino first?
“If the invite is there, I’ll certainly take it up,” Jackson says. “He’s one of the best in the world. For me, it’s a great opportunity to come up against someone like that.”
The Wimbledon boss needs no added motivation, but a win at Stamford Bridge would be particularly sweet for a man who supports Arsenal and played for Tottenham.
“A lot of my pals are Chelsea fans and they’ll be in the crowd,” Jackson says. “For us as a club, and for me personally, it would be unbelievable to win. If we do, I’m sure there’s going to be some messages flying about!”