Raptors president Masai Ujiri – who said he was confident Toronto would re-sign Leonard before Leonard chose the Clippers – seemed to hint someone in Leonard’s camp wasn’t up front during negotiations.

Now comes more evidence we should read between the lines with Ujiri’s latest remarks.

Josh Lewenberg of TSN:

That confidence began to waver after they met with Leonard and his uncle Dennis Robertson in Toronto last Wednesday, sources told TSN. That’s when they first questioned the intentions of Leonard’s camp.

Robertson has a reputation for being hard to deal with and would have been hands on throughout the process. According to sources, Leonard and his camp – namely Uncle Dennis – asked for a lot from the Raptors in that meeting, things players don’t generally ask for in standard contract negotiations. In some cases, they were asking for things that Ujiri – one of the most well-compensated executives in the league – wouldn’t have even had at his disposal. Their requests were “unreasonable”, a source said, which made the Raptors wonder whether Leonard was seriously considering them at all.

Leonard clearly had eyes for Southern California. Toronto was facing an uphill battle.

Wouldn’t the Raptors rather know what’d it take – even if it was outlandish – to keep Leonard?

Maybe Robertson’s requests were unreasonable. But that’s not for him to decide. He probably gave Toronto accurate parameters for what it’d take to keep Leonard. The Raptors just couldn’t do enough, not after the Clippers got Paul George.

This is a relatable situation. When presented a job opportunity you probably don’t want, it’s OK to make exorbitant requests. If the employer wants you that badly and agrees, great. That undesirable job became desirable. If the employer can’t/won’t make it happen, you pass on a job you didn’t want anyway.