While our time under Roland has been by a large a catalogue of errors, looking back there are several occasions where if one thing did/ didn't happen we could be in a totally different situation to what we are now.
What if Igor didn't get injured 6/7 games in?
What if Arsenal didn't have the most injury prone midfield ever and we actually kept and signed Coquelin on a free?
What if they didn't manage to mess up the easiest signing ever in Bulot?
What if Gradel did decide to join?
What if they didn't sell Yann for a portion of chips?
There are more of these but I think these are the main ones. I genuinely think that if any of these happened (particularly the Coquelin one) we could have been up in the playoffs in the championship that season and who knows at that point Roland might've opened his wallet a bit more.
This isn't making excuses for them in the slightest and if anything it makes our situation now 100x times worse but obviously hindsight is a wonderful thing but it's hard to look back and say we weren't close. I don't know why I'm thinking of this now but I suppose it's easier to look back at when it wasn't going too badly compared to our future which I don't even think Roland knows now.
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What if Roland wasn't an arrogant, misguided fool? What if Daisy wasn't lazy and incompetent? I don't think there's any way around those.
Biggest what if? If the comfort blanket "support the team not the regime" was seen by all as the obvious nonsense it was/is?
They didn't "mess it up". They weren't willing to pay the going rate for a player of that standard. Just one part of a long-standing policy, rather than a one-off mistake.
What if Gradel did decide to join?
If we were ever actually in for him in the first place. All of our transfers are for undisclosed fees, except the ones that we don't manage to get over the line, which are always ambitious, big money signings. Gradel £1.5m, Delort £3m, some bloke from Rotherham last January for £2m, there's been others as well. Doubt Gradel was any closer to signing for us than I was.
After that, you fix the obvious issue; the squad hadn't been added to sufficiently since promotion due to a lack of funds. Roland was in the perfect position in that he had money and a management team with a proven track record of being able to pick a player, often one who had fallen out of favour or been under-utilised elsewhere, and get more out of them than anyone else had. Incidentally, it's the opposite technique of what we have now; Robinson tries to cram the random 'they look good on a spreadsheet' signings he's given into his formation, whereas Powell knew the style and mentality he wanted from a player and picked the man accordingly, regardless of what he'd done elsewhere. He knew he wanted Leicester laughing stock Yann but had no interest in free-scoring Leon Clarke. Guess who was the better player for us. All Roland had to do was ask Powell which players he felt could fix Charlton's league position in January and we would have stayed up with no trouble whatsoever. Powell's shopping list at the start of our first Championship season was Hammond, Bolasie, Shackell, Quinn and Aluko, all of whom subsequently got promoted with other teams. He wasn't the perfect manager tactically but I don't know if we've ever had a coach who knew the players he needed quite as well as Powell did. It wouldn't even have cost that much as the great thing about bringing in unwanted players is they go for cheap.
It all comes down to arrogance with Roland. Why renew Hamer's contract when you've got Thuram? Why even keep Alnwick around when Thuram is there? Why get in proper cover for Solly's knees when you've got Nego? Why keep Yann when Parzyszeck is cheaper to pay? Something something bloody Reza. Things could have been so different if he'd just listened to the experienced staff he had. If he still wanted to be a bastard he could have let Powell have the transfer window to identify quality players, bring them in and sack him afterwards. That would have satisfied Roland's desire to be the absolute worst and left Charlton with a decent squad. Instead he did the most damage he possibly could in one month. For me, that period with Powell was the happiest I've been as a Charlton fan in a while. I'll take us being crap, in League One and never quite getting anywhere, it sort of goes with the territory, but for once we had everything. We had a management team up to and very much not including the owners who cared about Charlton, decent likeable players and a bit of a bounce. The fact we could have made the Play-Offs with just a small amount of intelligent investment is just heartbreaking when you compare it to where we are now.
These things will always stick out for me more than selling THD too cheaply and missing out on Bulot. The ship was sunk a long time ago
Yann was the big mistake, as he wanted to stay. Morrison did sign a new contract, then got pushed out...
Going back to the original question, another might be
What if a year ago, we had appointed Warnock instead of Rotherham?
The longer this goes on and the more the word goes round we will never attract a manager worth having, just the has been's that float around picking up a wage and the pay off when RD sacks them.
Roland didn't have a pot to piss in so we didn't even know who he was.
We'd be in the championship.
Probably moaning about something not even realizing how lucky we are.
Be grateful.
He could have kept the basis of that squad and with and couple million a year he found have built something. We would have had a damp good go at getting there. And it would have been at hell of at lot cheaper than what has happened.