And here's my situation.
1st season:
Got 10 day contract from Magic, another 10 day contract from them, and a whole year contract. (And I got Jackson Ellis cutscene, I can't remember when it happen.)
We got to the playoffs, Win the Finals, I am the Finals MVP.
2nd season:
Sign with the Knicks played 10 games.
And Jackson Ellis cutscene for the 2nd time and told my player "Got a long way to go.".
But there's another cutscene in my home, talking to my agent and my player is complaining what JE said but my agent told me that adidas wanted me to sign to them.
So my agent ask me what brand to choose, I'm a sneakerhead so it's obvious that I will choose Jordan all the way. (Sorry forgot to take a screenshot.)
2 games after that. JE is on my home talking about the dream come true deal.

For what I've notice to those who don't still have the deal is that they sim games.
BTW, I force my player to average 30-40+pts and 6+ assists every game.
Because you need 40+ pts and 6+ assists to impress State Farm.
I'm sure Jordan and other brand is much harder to impress than State Farm.
Thank you! Sorry for my bad english.