Five Questions That Define New York's Offseason

With a new front-office staff, new head coach, and another lottery pick in this November’s NBA draft, the Knicks still have plenty of questions to answer on how they want to right the ship moving forward.

Last offseason, we were dealing with what was called: “The most important offseason in the history of the New York Knicks.”

Despite another losing season, the Knicks awaited the draft lottery, in hopes of acquiring then-Duke forward Zion Williamson. Then, they had a chance to hit the jackpot in free agency—adding Kevin Durant and Kyrie Irving—to complete one of the best offseason hauls in recent memory. At the time of writing the last offseason, Durant was a month away from his first injury against Houston in the NBA playoffs.

It’s safe to say things didn’t go as planned. Irving and an injured Durant joined forces in Brooklyn, while Williamson ended as an Anthony Davis replacement in New Orleans.

Today, New York’s expectations have lowered, thanks to a weaker draft and free agency class, but also because of the new management and head coach. Instead of attempting to win an instant title contender, the Knicks are merely looking to move out of the cellar of the Eastern Conference while developing their young players along the way.

Still, there are questions regarding how the Knicks will ultimately go about that. Though the stakes aren’t quite as high, the Knicks still have to build their roster, and some key decisions will be made along the way. Here are five key questions surrounding New York’s 2020 offseason.

1. Which players will make up New York’s young core?

Before the Knicks can add talent to the roster, reflecting and evaluating the current young core of players is a must. As one regime departs and another enters the fray, reassessment is needed. The Knicks have several guys on the roster under the age of 23. Let’s take a look at them. I’ve ordered them by age and how many years remaining on their rookie contract.

Note: Kenny Wooten is a restricted free agent this offseason as a G League two-way player. Kevin Knox’s fourth-year option has not been picked up. The assumption is that they will pick that option up, making him an RFA in 2022, rather than a UFA in 2021.

That list is before you consider the Knicks have three picks in the 2020 NBA Draft, including the eighth overall pick. If the Knicks were to use all there of their draft picks, New York’s roster could have as many as 10 guys under the age of 23. Ultimately, something has to give, as new head coach Tom Thibodeau will look to bring in players who fit his criteria.

Right now, Mitchell Robinson and R.J. Barrett seem like the young building blocks for this current regime, but Robinson’s pending free agency status could complicate things if negotiations go poorly. Frank Ntilikina is a restricted free agency next summer, but his versatility on offense and defense could make him a staple in Thibodeau’s first rotation. Let’s assume that whomever the Knicks take with the eighth overall pick is an instant rotation player, since he will be approved by both the front office and Thibodeau.

Everyone else? It remains to be seen. Kevin Knox has struggled through his first two seasons, even though he has a relationship with current assistant head coach Kenny Payne. Dennis Smith Jr. was a favorite of Thibodeau at some point, which could create an interesting battle of who stays between the two. Brazdeikis, Wooten, and the 27th overall pick could see their time split between the parent club and the Westchester Knicks.

The Knicks are entering another period where they’ll have to make a decision on whether to keep their young players, and the likes of Smith, Knox, and maybe even Brazdeikis could find themselves elsewhere as Thibodeau and Rose tweak the roster.

2. Can the Knicks properly leverage their cap space?

Thanks to last offseason’s disaster, the Knicks are once again entering the offseason with a sizable amount of cap space. Spotrac, a website that covers all sports and their financial situations, has New York with $48.2 million in space, while Yahoo Sports’ Keith Smith has New York with $42 million in projected space. Whatever the exact number is, the Knicks are one of four teams with upwards of $30 million in space this offseason.

So far, we’ve seen New York attempt to leverage their cap space in a potential Chris Paul trade, but the Knicks should be more creative in attempting to find both players that can help the team and assets for the future.

Currently, the Knicks are asset positive, with the Los Angeles Clippers’ 2020 first-round pick alongside two Dallas Mavericks first-round picks, 2021 and 2023, coming down the pipeline. Still, for a team that wants to both take a step forward now and have the appropriate assets for the future for a superstar trade, using some of their cap space to acquire more assets would be a fair alternative to investing heavily in this free agency market. Last season, New York panicked and added nine players and no assets. Could this regime capitalize on their cap space?

Could you get Danuel House Jr. from Houston to help their tax woes? Can you get a future first-round pick to take back Terrence Ross’ contract from Orlando, a team with two big-name restricted free agents (Jonathan Isaac and Markelle Fultz) in 2021? If Milwaukee wants to move off of Eric Bledsoe’s contract, the Knicks could be there with cap space to assist. What about Denver looking to re-sign Jerami Grant and shuffling Gary Harris off the roster? The Knicks could help there as well.

There are several options and routes the Knicks can go with their cap space, while also remaining flexible. With a new front-office staff, hopefully the ‘Bockers can be a bit more advantageous in their pursuit of adding assets.

3. How much are the Knicks planning to invest in development?

In a complete front office reboot this season, the New York Knicks completely redesigned the front office, one that made several people believe that this rendition of the Knicks front office will lean towards the development side of things.

Assistant general managers Walt Perrin and Frank Zanin come from two teams, the Utah Jazz and Oklahoma City Thunder, respectively, with strong backgrounds in player development. They’ve largely flipped the scouting department with four new scouts added this offseason and Thibodeau, with a fairly decent development track record, brought in Kenny Payne from the University of Kentucky and Johnnie Bryant from the Utah Jazz—both of whom were praised for their development from current players around the league.

All of this is great, but does this mean New York is taking a deep dive into scouting and team-building for the foreseeable future? They can start with their current roster of young players—Barrett, Robinson, and Ntilikina. All three have their own flaws: Barrett and Ntilikina can take steps forwards as a shooter, Robinson could use improvement on his defensive positioning and defensive rebounding—so working there could help their immediate future.

It remains to be seen if the Knicks redesign trickles down to their G League team. As of now, there’s no telling whether we have a 2020–21 G League season. However, if they do, the Knicks should push to revert back to their old pattern of G League development, unearthing players like Langston Galloway, who went from an undrafted college player, to a G League gem, to legitimate NBA player.

If they do have a season, the Westchester Knicks could have a few players of intrigue. Brazdeikis had a solid season as a rookie and could use another year of seasoning before receiving a shot at the main roster. Kenny Wooten is a great shot-blocker and rim runner but struggles to shoot. If he can take a small step forward as a shooter, Wooten could be a role player option for 2021.

New York has seven draft picks in the next two years and an overture of first-round draft picks over the next five years. If the Knicks are moving forward with an eye towards improving their development practices, a shooting coach and a new scouting department are solid steps forward, but improving the G League would be another strong step.

4. What are the Knicks going to do about their point guard position?

A tale as old as time: the New York Knicks could use help at the point guard position. Elfrid Payton came in a stopgap free-agent addition, while Ntilikina, often shuffled between the bench and shooting guard, found himself starting alongside Barrett before the abrupt end of the season. Both players had positive moments, but neither looks like starting point guards moving forward.

This offseason and the rumors have been focused on figuring out that answer, but will New York do that for the short-term or for the long-term? How about both?

The Chris Paul rumors have persisted throughout the offseason, while talks of Russell Westbrook have peaked as the Rockets saw their general manager, Daryl Morey, opt to leave the franchise. Both players are talented, but also older and expensive. Neither seems to be long-term options to fill the position. Free agency offers Fred VanVleet, who could get expensive, but could be exactly what New York needs.

The draft, as always, offers the long-term option. LaMelo Ball rumors, much like the Paul talk, have been buzzing throughout the offseason and recently picked up as New York is interested in acquiring a top pick. Other names, like France’s Killian Hayes, Iowa State’s Tyrese Haliburton, and Alabama’s Kira Lewis Jr., could be options with New York’s lottery pick, the eighth overall pick.

If New York opts to trade for Paul, the Knicks could select a point guard at the end of the first round, therefore doubling down on the position. North Carolina point guard Cole Anthony would be an interesting option if he fell to no. 27, but the likes of Duke’s Tre Jones, Kansas’ Devon Dotson, and San Diego State’s Malachi Flynn could all entice New York as a backup point guard.

This summer offers a rare chance for New York to solve the point guard position—it just depends on whether the Knicks want to make the long-term investment or will they attempt to go for the (talented) stopgap in Chris Paul.

5. What are the ultimate expectations for the New York Knicks in the 2020–21 season?

Probably the toughest question to answer: what are the expectations of the New York Knicks for the 2020–21 season? What is considered a success for the Knicks next season? Where do the Knicks want to be heading into the 2021 offseason where there is some level of normalcy in the world and a group of players one step closer to free agency.

If New York decides to attempt to make steps forward and fall in the middle—remain in the catacombs of the league for the 2020–21 season, but attempt to compete the following season—then a Paul trade or VanVleet signing make sense to help shore up the point guard position. Adding a floor-spacing big man like Davis Bertans or Jerami Grant would help those endeavors as well.

None of these moves make the Knicks good enough to avoid the lottery, but they help New York take a step forward. The addition of Paul gives New York an elite playmaker who can make life easier for New York’s young players. The likes of VanVleet and Grant offer shooting and defense to help open spaces for the likes of Barrett and Robinson.

If the Knicks decide to “tank” for another season, then New York can opt against adding a big-name player for more modest free agent adds. Players like D.J. Augustin or Jeff Teague to hold down the point guard position, or Alec Burks and Justin Holiday to space the floor on the wing, or even JaMychal Green as a shooting big, to help balance New York’s roster.

The New York Knicks don’t have the same pressures as last season, but the questions still remain on how they want to build this roster. With several players on the roster, the Knicks have young players to work with, draft picks to use and cap space to add talent to it. While the roster is young, Tom Thibodeau and Leon Rose doesn’t seem like the type of figureheads looking to sit out a long-term plan, putting pressure to flip this into a contender right away.

For now, the Knicks have to find players who can help in the long-term, figure out the best way to manage their draft picks, and eventually properly navigate the roster so they can pursue an available superstar when the moment arises. Until that moment, the Knicks are wide open to do just about anything. It remains to be seen whether they want to speed the process up with free agent acquisitions or attempt to develop their kids first.

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