He left United halfway through the Champions League adventure that was to mark the end of Peter Ridsdale's tenure and the start of the downward spiral.
Perhaps Pearson could see the writing on the wall, although he maintains that his reasons for moving were solely to do with the potential he saw at Hull City.
Either way, it is tempting to surmise that some of the excesses of the latter days of the Ridsdale era might have been avoided if the commercially-astute Pearson had been still around.
He told the Yorkshire Evening Post:
"It's difficult because I was on the outside when a lot of those decisions were made and so I don't really know what the rationale was for taking them and it's not for me to comment on what's gone on at other football clubs.
"But I think it's fair to say that what's happened over the last year or so at Leeds hasn't really come as a major surprise.
"I think the writing's been on the wall for a bit of time now and things have finally caught up with the club.
"When I left Leeds, we'd just turned over £80m and made a £10m operating profit.
"But football's changed and I think Leeds got left behind a bit when that change occurred.
"That was three years ago and since then there's been a massive decline. There are lots of factors involved in that, but I have to say I was unsure as to why the large-scale purchase of players continued for so long.
"From the outside you were looking at a club with four or five world-class players and yet they still went out and paid £9m for Robbie Fowler. Leeds are still paying for those signings now - literally in some cases - and that's a situation that John McKenzie is having to get to grips with."
In many ways McKenzie's situation now is very similar to the one Pearson found himself in when he took control of Hull in March 2001.
The 38-year-old bought the club for just £360k but was immediately forced to clear debts of more than £1.5m.
Two years later and, while they may still be in the third division, they are debt-free and even turning over an operating profit.
It may be a while until McKenzie can make the same boast at Elland Road and Pearson sympathises. "Being a football chairman can be the best job in the world, but it can also be the most challenging.
"Unfortunately a lot of it is about experience and learning from your mistakes. I did six years at Leeds before I came to Hull but there's no doubt that mistakes were made in my first year here. We were carrying too many players and it took a while for things to settle down to a realistic level.
"But being a football chairman has changed massively - even in the short time I've been involved. Years ago the chairman just stayed in the background and signed the cheques. Now the position is so high-profile and the chairman is under as much scrutiny as the players and manager - if not more.
"There's always going to be pressure from the fans, but I can sense a slight change there over the last couple of years, especially at clubs like Hull who have been through the bad times.
"It used to be that the only pressure that came from supporters was to sign players. Now it seems to have gone slightly the other way and they want a chairman that doesn't get done over in the market place.
"Fans know about the financial realities in football now and I'm going into every deal thinking about the ramifications and risks of how that deal will stand up in two or three years time.
"I was able to pick Hull up for a small amount of money because they were in administration and in all sorts of trouble," he said.
"We invested an awful lot of money in the first year and made a big loss, but this year we'll break even and next year's figures look like being very healthy indeed. We trade profitably from month to month now and I dare bet there's not too many clubs anywhere in the country that can say that.
"The wage bill is down to less than 40 per cent of our annual turnover and we've got no debt. I own the stadium management company so we've got one of the best new stadiums in the country and we own it outright. We control our own destiny and we can plan with the confidence a lot of other clubs don't have.
"That's taken a while though and some difficult decisions have had to be made along the way. But the position we've got ourselves into now show that those decisions were the right ones.
"We're certainly optimistic about the new season, we're not going to go shouting about it because that's a criticism that's been levelled at us in the past - probably with some justification.
"I think in the past we've been guilty of having expectations that have maybe got beyond us.
"But part of that comes from the knowledge of what we could be sitting on here at Hull.
"The football club is an integral part of the city - there's such a strong bond there - and that inevitably creates its own excitement and expectation.
"There's no doubt in my mind that this city could sustain a successful football club."