It’s time for the Knicks to answer three questions: Where will the Knicks be on deadline day, where might the Knicks be in early March and what the Knicks could be the next two seasons.

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The New York Knicks were never expected to make the playoffs this season. This is a team that was predicted by ESPN to finish with the sixth-worst record in the NBA, and that was before the Carmelo Anthony trade. This is a roster largely devoid of talent and caught between two different regimes, with four players on the wrong side of 30 and five players 24 years old or younger.

Back in October, I wrote about how the Knicks are developing as opposed to tanking, and the difference between the two concepts. It has never been about making the playoffs this year for New York; after all, you don’t trade your best win-now player and expect to make the postseason.

On February 8th, New York must answer three questions in regards to selling at the deadline: Where will the Knicks be on deadline day, where might the Knicks be in early March and what the Knicks could be the next two seasons.

Where will the Knicks be on deadline day

The Knicks have lost five of their last eight games and are 4–14 on the road this season. They’re one-fifth of the way through a month where they play 16 of their 20 games on the road. Once January concludes, New York has three games before the trade deadline: one away (Milwaukee Bucks) and two at home (Atlanta Hawks and Bucks). If the Knicks continue to lose on the road, they’ll fall further back in the playoff hunt and it might be too late.

Where might the Knicks be in early March

Once the deadline passes, the Knicks play three straight away games against the Toronto Raptors, Indiana Pacers, and Philadelphia 76ers, a home game against the Washington Wizards, an away game against the Orlando Magic and home games against the Boston Celtics and Golden State Warriors. The Knicks then start March on a four-game road trip against the Los Angeles Clippers, Sacramento Kings, Portland Trail Blazers and Bucks before coming home to face the Raptors.

As of this moment, the Knicks are almost as close to being tied for the 10th-worst record in the NBA (three games) as they are for holding sole possession of the eighth seed in the East (two-and-a-half games). If the Knicks aren’t near .500 by the deadline, there’s likely little chance they’ll be in playoff contention after the Raptors game in March, even with a healthy Hardaway. Road woes and injuries could lead to the Knicks dealing at the deadline, which could then trigger an intense focus on developing young players. A top-five pick may be out of reach but a pick in the six to 10 range could be possible depending on who is traded, who is healthy and who is playing meaningful minutes in March and April.

So the Knicks front office could say in less than a month from now, “Look, whether it was injuries or a lack of prime talent, this isn’t our year. And that’s okay because this is year one of a three-year plan for contention. The 2018 schedule hasn’t been easy before the deadline and it won’t be easy the rest of February or the beginning of March either. Let’s gauge the market on some of our players but we shouldn’t sell solely for the sake of selling.”

What the Knicks could be the next two seasons

It makes sense to trade a potentially expiring contract and possibly a long-term contract at the deadline to free up some cap space for this summer. Yet how much win-now talent should New York be willing to trade since the realistic plan will be playoffs next year?

There are certain ramifications that can come from the trade deadline. For example, the Knicks could capitalize on Courtney Lee’s high trade value but how does that affect the team’s playoff chances next season? If the Knicks feel Lee can help them get to the playoffs next year, is it necessarily worth it to deal him this February? So how far does New York go in terms of selling? And what might certain transactions mean for the future in terms of performance and financial flexibility?

2018

If you think the Knicks are going to gut this team at the deadline this year, think again. New York simply will not sell off every useful player who is over the age of 26 for whatever the team can get in return.

Surely the team will want to contend for a playoff spot in the 2018–19 season, so dealing an abundance of players just to net some low-reward assets wouldn’t benefit the Knicks in the long term. The front office values leadership and character, and stripping the team of almost every veteran sends the wrong message to its young and potentially impressionable players like Kristaps Porzingis and Frank Ntilikina.

One thing New York does have to consider is its future cap space with several moving and unknown parts involved. While Kyle O’Quinn is expected to opt out of his contract, Enes Kanter’s $18,662,513 decision doesn’t appear to be as clear. Does Kanter opt in, take the money now and bet on himself to perform well and stay healthy, or does he opt out in search of long-term security, even if it costs him given the shallow market for expensive big men? Ron Baker has a player option, although it’s hard to imagine he’d decline it. It will likely be a waiting game for New York this summer.

If the Knicks can clear enough money for this summer, what free agents will a) be available and b) want to sign with a team that could spend its sixth straight year with a bottom-10 record? Going after big money free agents in their prime makes little sense when Porzingis will be 23, Ntilikina will be 20 next season and New York has a contractual albatross with Joakim Noah.

Perhaps New York looks towards the restricted free agent market and tries to lure a younger player like Jabari Parker, Julius Randle or Kyle Anderson away from their respective teams. If New York can add one of these types of players and a top-10 pick in this year’s draft to the trio of Porzingis, Ntilikina and Hardaway, the Knicks will have a formidable young core. This is important because they can then make their pitch to max-caliber free agents the following season by saying that they have added talent through the draft and free agency each of the previous two seasons.

2019

In order to attract a max-caliber free agent, the Knicks would need to a) win next season and b) have money at their disposal. One would hope that a fully healthy squad of Porzingis, Hardaway, Ntilikina, the RFA signed, the player chosen with the 2018 first round pick and other contributors makes the playoffs in the East. The money part isn’t as challenging as one may think, but it also depends on the outcome of this year’s trade deadline.

Let’s talk about Lee again. How do the Knicks feel about paying a 33- and 34-year old Lee a combined $25,013,450 over the next two years? The Knicks will need some sort of financial relief with another eventual 33- and 34-year old Noah being owed $37,825,000 over that span of time. Lance Thomas is under contract for the two seasons after this one as well, yet the final year of his deal is non-guaranteed. If the Knicks decide not to guarantee Thomas’ contract, he would only receive $1,000,000 of the $7,583,975 he is eligible to receive.

New York won’t trade both Lee and Thomas at this year’s deadline because of leadership. The Knicks won’t and shouldn’t trade their two co-captains at the same time. What New York could do is trade Lee while his trade value is at its highest for an asset and a contract that expires after the 2018–19 season. Thomas can then be kept next year so that the club isn’t devoid of a leader. After that, if the Knicks wish to open up more cap space in summer 2019, they could:

Non-guarantee Thomas’ option

Dump Noah’s expiring contract (plus a sweetener) on a rebuilding team with excess cap space

Refrain from signing Porzingis to an extension until after they look for upgrades on the market, as the difference between Porzingis’ cap hold and him signing a max contract in 2019 is more than $10 million

Here’s what the Knicks’ salary situation would look like if:

The hypotheticals above actually happened

New York didn’t sign, re-sign or trade for a draft pick or a single player under contract past the 2018-2019 season (simply won’t happen but too challenging to predict with two deadlines and two free agencies to come)

The Knicks picked up their team option on Ntilikina and guaranteed the contracts of Damyean Dotson and Willy Hernangomez

All players not named Porzingis had their cap holds renounced

The players drafted in the second round of the 2019 draft were all draft-and-stash

There is a 100% guarantee that this is not what the roster looks like, verbatim, by summer 2019. This is merely a way to show how the Knicks could open up over $50 million in cap space two summers from now, especially if they strike out in free agency this summer.

Bottom line

The Knicks could acquire future assets to build around their young core, but that could also come at the expense of losing more games than the team would like next year. For some players deserving of max contracts, winning is more important than money. LaMarcus Aldridge, Kevin Durant and Gordon Hayward turned down more money for what they felt was a better chance to win elsewhere because they would already be earning a colossal amount with their new team. If the Knicks want to prove to these types of players that they can win, they need to show progress. It’s hard to do that with a team stripped to its core for unknown assets.

This is why this year’s trade deadline is so challenging. While the trade market should be gauged for some veterans, New York must show consistency on the court. What is the correct balance between selling and gutting the team, and what effect does it have on future winning and financial flexibility? Only Steve Mills and Scott Perry know the answer.