I admit it looks like that on the surface but what if the plan IS to do this ?
Realistically KW started with the costliest player first, he gave Milford a fair chance and Milford absolutely had no doubt or confusion whatsoever about the opportunity. He knew he was being tested and graded. He knew it was all on the line to get a contract somewhere.
He gave him 5 games.
He moved on to Croft and Dearden. Tried them out. They largely failed too. Milford begged(I believe, don't know) for another chance and went okay in ISC and got one more chance. Failed again. So Dearden is out the door and I'd say KW was aware he was long odds on to leave. So he's got Croft left. Okay, KW figures, nothing left to test in these three, let's start testing the next lot.
Croft is now out injured so Gamble stays because he probably listens and values his chance. He's in the test bed stage still. Next test subject Kelly, let's see what's left in the tank. If he fails I don't see KW turning to Dearden or Milford again so if this pairing perish then I think KW has been give permission to keep on testing.
I think the club identified that this year was like Boca Chica, a testing ground. KW was probably more optimistic than the club I think. He probably thought he could turn the club around to at least 8th but I think the bosses knew better yet hoped KW might fluke it.
I will not be surprised if we see a few surprise guest test subjects over the next 13/14 weeks. I hope Isaako gets a shot just so I can be King Toldyaso from the Shire Of Ipswich