Fourth-placed finishes, the expensive move to a new stadium and season upon season of prudence in the transfer market.
Those things may have all been a source of frustration for fans (and incessant bleating from Piers Morgan), but 20 years after Arsene Wenger took control of Arsenal the club has cemented itself as one of world football's financial powerhouses.
Arsenal find themselves in seventh place in the Football Money League - part of an annual report by financial consultancy giant Deloitte - which tracks the highest revenue-producing clubs across the world.
In the 1996/97 version of the report - the season Wenger was appointed as manager - Arsenal sat way down in 20th place on football's rich list with a revenue of €36m - below the likes of Parma, Ajax, AS Roma, Flamengo and Newcastle United.
Fast forward to this year and the club has produced €468.5m (£350.4m) in revenue - thanks to matchday income, broadcast rights and commercial sales and now sits above European giants like AC Milan and Juventus as well as London rivals Chelsea and Tottenham Hotspur.
Deloitte's Football Money League
But with financial security does not necessarily come on-pitch success.
While the first half of Wenger's reign in north London brought 11 trophies - including three Premier League titles - the second half has been characterised by settling for Champions League qualification, big name players leaving in search of silverware and constant chants of "Wenger out".
Last season fans from protest groups held up placards at the club's match against Norwich demanding: "Time for change. Arsenal is stale, fresh approach needed."
After the game, Wenger said his critics had gone "too far". Referencing the £390m move to the Emirates stadium in 2006 - a big part of Arsenal's current financial success - the Frenchman defended his record in light of the burden that placed on him and the club over the past decade.
How Arsenal's revenue has risen in the past five years
"When we built the stadium the banks demanded that I signed for five years," he said.
"Do you want me to say how many clubs I turned down during that period?
"The banks wanted the technical consistency to guarantee that we have a chance to pay them back."
Arsenal revenue breakdown
While Wenger has frustrated fans, there's no doubting that those top four finishes - something the club has achieved 20 seasons in a row - the successful transition to a new 60,000-seater stadium and maintaining a strong position in the Premier League as its mega television deals have poured in have all gone a long way to securing Arsenal's long-term future as one of the world's richest football clubs.
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