Kyle Lowry signed for 3 years for 100m at the age of 31 this off season. He averaged 22/7. Now I'm just going to roll with the premise that IT will be playing at a similar level of Kyle Lowry when he turns 31 which to me seems highly likely.
If I'm IT's agent and I want to maximize my clients money over a longer period of time I would urge him to sign a 2+1 max contract. Opt out of the third year as long as you play how you are expected to and then sign a Lowry type deal at age 31 for 3 or 4 years.
This move could potentially make IT another 25 million more dollars over a 5 year period when compared to straight up signing a 5 year max contract next off-season. It could also give him a much higher chance of being paid dramatically more in the 6th year (if he managed to turn that Kyle Lowry type contract into a 4 year instead of a 3 year) Ultimately the move could generate him 35-45 million more over 6 years if he did get that 4th year (unlikely but possible).
After IT's proposed 2 year contract is up he will have more then 10 years experience making him eligible for 35% of the cap, and the cap is expected to be around 110 million in 3 seasons..... both of these things play a pretty big role in IT making 20% more money over 5 years.
But it's not too outlandish to think about doing this considering it's exactly what Gordon Hayward just did, as he will be opting out in 3 years and signing a new much larger max deal that will have made him roughly 25 million more over the next 5 year.
The only way the plan would backfire is if he got very seriously injured in his contract year, but that is why you do a 2+1, opt into that +1 to get back to healthy and on the court to show people you can still play. But, is that too great of a risk to take?
Also, I could be completely wrong since I am not a cap expert. Someone set me straight and tell me the obvious reasons why IT would much rather just sign a 5 year max next off season.