Look I don't blame Ole for his frustration. It's not his fault that Woodward finds it very hard to bring more then 3 players per summer, which in turn, forces us to keep or even give contract extensions to players who don't deserve it. In such cases the manager is forced to tone down and be careful what he would say and do because he can't just get rid of the players and expect them that they would be replaced.
Having said RVP was right, Ole is too nice and managers shouldn't smile after a defeat. That's something even Rio agrees with him as well. I wonder if Ole knows about Rio as well considering both players (RVP and Rio) were WC and first teamers, not some bench warmers.
Woodward is more than capable of signing more than three players. He did it for Mourinho, he did it for LvG and he would have done it for Moyes too, if Baines had agreed to come here and if dithering Dave hadn't been thinking so hard about how Kroos and Herrera would fit in his plans while at the same time being so sure that he wanted Fellaini. It's one thing for fans on a forum to discuss Woodward's failings but please tell me there aren't many people out there who took that tweet at face value and believed that the CEO of a major corporation actually came out and admitted in public his uselessness. What that tweet meant was "don't expect to be given much in the following transfer window(s)."
And the problem didn't occur now. After offering both LvG and Mourinho a war chest each just to see it go down the drain, Woodward has assumed a more cautious approach regarding the squad and the manager's demands. That's, presumably, why he fell out with Mourinho. The latter believed that a 2nd place finish and 81 points were enough to guarantee him additional funding but, at the same time, Woodward had the improvement the "other best manager in the world" had achieved during his second season just a few miles away from OT to compare it with. What made things even worse was that Mourinho targeted two players he knew and trusted well in Perisic and Willian. At that point, Woodward didn't trust Mourinho enough to overpay (as he and Judge usually do) for players that would help the Portuguese tactically but didn't seem to be of much use for any other manager. He also didn't trust him enough anymore to pay a record fee for Maguire. The idiocy in the whole thing was that he had renewed Jose's contract before he changed his mind.
The thing with Solskajer is that he accepted the job on these conditions. The plan he sold Woodward was one of promoting academy players and buying young & hungry (mostly) British players who understand the culture of the country and the club. And he would create a team capable of challenging for the big prizes in the near future while maintaining some standards on the way toward that goal. That's why Solskjaer always tows the line, he always talks about the future and he always points out the goods and the bads of a side full of youthfulness. That's also why the only time he chose to have a dig at someone was when he berated the internet fans for demanding transfers. O tempora o mores... one of the best defences his most ardent supporters use these days is the lack of transfers. He won't get them. Or he'll get one midfielder if either Matic is sold or if a player we can all agree might prove useful becomes available. 8/21 PL wins don't give you the "right", in Woodward's mind, to ask for more of "your" players. Woodward's made a mess but he's not an idiot to go down with a failing manager. It's Solskjaer's masterplan, after all. The Norwegian has to provide proof of improvement, Ed's just here to "protect the assets". Right or wrong, i don't know. What i do know though is that most of the people who want Woody's head on a plate for letting down Solskjaer had no qualms getting behind our CEO when LvG and Mourinho were in the same position. That's how Woodward survives.
And Woodward showed his "good faith" by sanctioning the record fee for Maguire he had denied Mourinho previously and by splashing 50 more million for one of the most promising RBs in the country. We also got James as a value for money transfer. But when Solskjaer listed Rice and Longstaff for 50-60 million each, Woodward became cagey. This is Perisic/Willian territory. Just as Mourinho wanted players who could carry the ball through the lines, Solskjaer wants players who can apply more active pressing by covering lots of ground. But unlike the highly acclaimed Maguire and the need for a new RB (we had none), Woodward was not ready to (over)pay for players only Solskjaer sees important for this type of money.
End of the line, Woodward is just being Woodward. But i get the feeling that Solskjaer drove himself into a corner by going fully idealistic with his targets and by believing that the academy could provide more solutions than it already has and that he could take more out of a squad that had previously let down renown managers with CL titles and finals under their belt. He overestimated his players and he overestimated himself and his coaches. That's the main reason we have reached new lows in terms of results and performances, not our CEO. The latter just doesn't make it easier for the manager.