The underlying personality matters first and foremost, but yes. That 'lack of effort' is exactly what overpaying looks like in certain people.
It is not always malicious.
Martial:
Obviously some people smarter than me thought I'm worth it just doing what I was doing. How am I supposed to know what they based it on. Maybe the other guys should work harder? I'm running a little bit more than last season. I'm definitely working harder than when I signed my deal, so I'm doing more than what they thought I was worth. Shrug.
That, one could argue in a sort of chicken vs egg fashion.
I'd argue that it's the underlying personality first that's the problem - they overpay themselves because they're narcissistic* and it's the narcissism that's destructive to the organization. There's a serious possibility that we're being run at least partially to provide
narcissistic supply for Woodward.
But yes, Woodward and Judge being overpaid can in and of itself damage the organization. AKA behind-the-scenes talk between other executives a-la "
Look at those morons out of their depth but paying themselves like they're winning the PL and CL every year." The danger then becomes having a giant 'KICK ME' sign on their backs of their own making; other execs/agents being afraid that not fleecing Woodward/Judge will make them look incompetent/weak amongst their peers, i.e.
You dumbass; even we got them to cough up 100k/week. You have to get your boy to at least 250k/week or you're going to lose out on some business in the future, I think.
If Woodward runs the place as a cash cow first for long enough, sooner or later other executives/agents start seeing it that way as well.
There's a scene in the movie
Kingdom of Heaven that encapsulates Woodward's personality perfectly. In it, the original king of Jerusalem says "I am Jerusalem" as he dispenses the law, meaning: "I am not 'me'. I am the collective will of the people. There is no 'me.'" The villain sees this, and projects his own self onto it and wildly misinterprets it. Later on, the villain becomes king and repeats this line, but he means: "ME, I am Jerusalem."
That is exactly Woodward's attitude towards the club and it was especially prominent in the early days. Quotes like Watch this space. Disneyworld for adults. Schweinsteiger-spine-tingles. The way he sacked Rio. All these were dinner-bells to skilled manipulators who know how to prey on narcissists.
Yes, it is. But on the second sentence, not necessarily. They're still money-men and will be able to adjust to financial realities if necessary. But those core narcissistic needs to 'be the big man' and to delay embracing/to ignore the fact that they don't know anything about football compared to other big clubs' executive structures doesn't just go away.
We are swimming against the current as long as Woodward is around.
*TLDR crash couse: narcissim isn't necessarily Trumpian braggadocio. It's an individually varying mixture of fear (terrified of hearing they're not as good as they think they are), ignorance (don't know that they're not as good as they think they are), and attention-craving (want to be constantly reassured how good they are). From there, you get endless combinations.
I just cannot take it anymore.