Here's how I see it.
Maldini is aiming higher than what he thinks Elliott or the new owners will aim for. Maldini wants to challenge for and win the CL.
We always assumed that the new owners will renew Maldini no matter what, they'd be stupid not to. That's always been true.
What Maldini has done with this interview is to raise the stakes. He's basically saying "I'm the one who needs to be convinced to stay". He wants to know from Elliott or RedBird that they share the same ambitions. If they say the right things and guarantee him the funds to get the 3 players he wants and that they all share the same ambition to win, then we can carry on. If they sound less ambitious and talk about competing with the rest of the Serie A retards for the title every year, then he might walk away with his pride and a job well done, and his hint that Leao might want to leave too is another bit of pressure that the players want to raise the bar as well.
It's partly a bluff, i'm sure. He's using the insane amount of political will he's gained over the last three seasons to pressure the owners into raising the bar. He's doing it publicly and risking the consequences because that's the only way he can force the issue out in the light. They have to answer him now. They have to say yes, of course we agree with Maldini that Milan needs to challenge for the CL... If they renew him that means that they agree, and we can carry on with daPlan+. The other alternative is that Elliott or RedBird never cared about challenging, and the title was a pleasant but unplanned surprise, and all that mattered was CL qualification and the stadium. If that's the case, then Maldini walks. We'll know soon enough.
Maldini had this one opportunity before the closing to put immense pressure on RedBird (or Elliott) to declare their ambitions and to raise the bar. Had he stayed silent and signed the contract, then he's part of the team no matter what direction they take, and he has to toe the line. He's taking a big risk because if they have no intention of raising the bar then they'll make that clear to him and he won't be a part of Milan going forward and everything goes to shit.
I think what he's doing is risky but it's a calculated risk. He knows how important he is, for the players and for the fans. He has them all on his side. All he cares about is the sporting success of Milan and long term, sustained glory (as well as maximizing his contract and power, of course).
I didn't expect him to do this, I was hoping that this sort of thing was already ironed out and the management was clear about future strategy and direction. They might be, and Maldini is just playing his cards to make it all public before the new owners get a chance of changing the narrative, or maybe he's just frustrated that it's taking so long that his deals are getting delayed and agents are pressuring him to make a move or lose the deal.