Sorry DR, these are so hard to answer. How much did connors know and when??!? Agents don't usually hide these things from a players club. They try and work hand in hand to work through it together.
His absolute priority is to put Jake in the best position possible to earn his next mega contract.
So he could have tried to engage the dogs on an early extension discussion. But we've seen with dusty, lever, Kelly etc what waiting can do to a players value. Plus the new CBA was to be done. So that was probably not an option.
From here, connors needs to decide for himself whether he thinks Jake can turn things around. If he thinks he can, I'd be signing the shortest deal possible with his new club, and getting him back on the market when he's in top form.