Mandatory Credit: Brad Penner-USA TODAY Sports

The Knicks and bench guard Immanuel Quickley failed to agree on an extension ahead of Monday’s 6:00 p.m. deadline, and next summer just got interesting. In fact, so interesting that Knicks president Leon Rose may need to go off-script and gamble a bit.

For context, Quickley will be a restricted free agent in July. This means that whatever contract he agrees to with another team, the Knicks can keep him by simply matching the offer. In the meantime, Quickley will earn $4.1 million in the final year of his rookie contract.

All signs point to him being paid. The former Kentucky Wildcat averaged a career-high 14.9 points off the bench and shot nearly 38% from three last season. Quickley also showed noticeable improvement on defense.

Furthermore, on Monday evening, his 2020 draft classmate Jaden McDaniels, of the Timberwolves, signed a five-year extension worth $136 million. He’s a forward and not a guard, but still a very similar player to Immanuel Quickley. Cue Quickley and his agent Raymond Brothers aiming for a similar number.

Now, normally, we would go into the pros and cons of the Knicks re-signing or not re-signing Quickley as a restricted free agent. Instead, we’ll sum them up here and now. Immanuel Quickley has been a great sixth man for the Knicks, but probably wants to lead a team. New York just has to decide if he’s worth paying a starter’s salary to come off the bench and/or make spot starts.

However, there’s something else that Rose and his front office should be considering. It isn’t the years or salary in any potential offer for Quickley. Rather, the focus should be on how spread out the money is on his next contract. The Knicks did this very dance a decade ago with a popular player and ultimately decided not to match the offer.

That player? None other than overnight scoring sensation Jeremy Lin. He still played well after his short Linsanity explosion before missing the last month of the season and playoffs with a bum knee. Then came a three-year offer sheet from the Houston Rockets, and everyone figured the point guard-needy Knicks would automatically re-sign him.

Except, they didn’t. Lin went to Houston for two years before spending the next five with five different teams. New York, meanwhile, brought back Raymond Felton.

This was because Houston, then under veteran GM Daryl Morey, got creative with their offer. Lin’s contract with the Rockets was worth $25 million over three years. However, to scare the Knicks away, Houston made it so that the final year of the deal paid Lin close to $15 million.

This move is called a “poison pill” and its sole purpose is to make a restricted free agent’s original team assume more risk. In this case, the Rockets backloaded the contract to make the cap-strapped Knicks sweat. If they matched the offer, they would have to, in essence, swallow the pill and assume that $15 million cap hit. It worked, and Lin signed with Houston.

No disrespect to Lin, but Immanuel Quickley is far more talented. Lin was talented, but overall a system player who was it his best in a pick-and-roll heavy offense. Quickley, meanwhile, is a strong defender and budding playmaker who can also score in multiple ways. He’s ready to take that next step and lead a team as their starting point guard.

Now, for all we know, Quickley could just love being a Knick. Who knows? Maybe he’s more than happy to stay on as the sixth man.

But even so, Rose has proved shrewd in his roster construction, including spending a first-round pick on Immanuel Quickley. He has to know an offer sheet with a “poison pill” is a very real possibility. Furthermore, having Donte DiVincenzo on the team makes Quickley semi-expendable.

It’s a long time between now and July, and maybe the Knicks even trade Quickley midseason. Especially now that the Joel Embiid rumors have decided to resurface.

Regardless, the deadline is passed and Quickley will now bet on himself. Everyone should be watching, especially the Knicks.

Josh Benjamin has been a staff writer at ESNY since 2018. He has had opinions about everything, especially the Yankees and Knicks. He co-hosts the “Bleacher Creatures” podcast and is always looking for new pieces of sports history to uncover, usually with a Yankee Tavern chicken parm sub in hand.