Julius Randle's contract last hurdle for Knicks' front office

Julius Randle becomes extension eligible on Saturday. The veteran forward is fresh off his third All-Star season in the last four years. He is the original building block that helped Knicks head coach Tom Thibodeau develop a contending-level roster.

Randle's status as a 10-year veteran and potential max salary candidate could hinder his long-term chances of staying with New York.

"Unless Randle, 29, is willing to take a substantial discount, it is difficult to find an agreement that makes sense for both sides," Fred Katz of The Athletic wrote. "...The Knicks can’t throw away the gift Brunson gave them. They cannot go above the second apron this upcoming season...It means Randle may have to take far less than $40.5 million in starting salary to entice the Knicks into handing him a new contract this summer...The question that follows Randle around isn’t just about the paper he will either sign or leave blank. It’s also about the jersey he will wear."

Randle has earned the opportunity to sign a hefty contract. He's been an integral part of the Knicks' rebuild. He has thrived as both a primary offensive option and, more recently, a high-level secondary weapon alongside Jalen Brunson.

Nevertheless, the Knicks must protect their cap flexibility to avoid the pesky second apron and retain some roster flexibility in the coming years.

New York wants proof that Randle's injury issues will not linger. He only played in 46 games for Thibodeau's team last season. Fortunately for the veteran, he has a strong history of availability. Still, the Knicks will want to be sure they're allocating their cap space to the right places.

Randle must decide how much money he will leave on the table. New York will likely prioritize cap flexibility and avoiding the second apron. If the two parties can reach an agreement that potentially backloads his deal so he earns less at the start of the contract, then a potential deal is highly likely.

However, if Randle stands firm on his value , the Knicks will have a difficult decision. At that point, there could be one more major trade before the Feb. 6 deadline.