When Wyc was on the broadcast last night, he said that a Jrue extension is a priority but it really depends on what he wants - and what DWhite wants.
Holiday is extension eligible on February 22 but can only extend for 2 years. If he waits until the end of the year, he can extend for 4. It really depends on how deep Wyc's pocketbook is - is he willing to have JT and JB on maxes and KP at $30M and Jrue at $30M-$40M and DWhite at whatever he's playing himself into?
I mean sure they could have agreed to pay Nesmith but they could have paid Grant as well and chose not to do it. $11M for a guy that's a team may not be able to play in the playoffs is a lot.
My larger point is that it's hard for contenders (or contender wanna-bes) to draft, develop, and retain young players. If a player shows some potential, there's likely another team that is willing to pay for that potential, meaning it's possible to lose that guy for nothing in RFA (i.e., Immanual Quickley; it also will be interesting to see what GSW does with Moody and Kuminga) or if the guy pops, the team can sign them to a big contract but then they get into MIN territory, where they have $152M-$160M committed to four players - Gobert, Towns, McDaniels, and Edwards (his salary apparently depends on whether he makes All-NBA this year). And losing Conley would really hurt that team IMO.
Obviously not impossible but teams face lots of hard questions when it comes to adding good young players to an existing salary structure.