James Dolan, owner of the Knicks
USATSI

Where do you see yourself in five years is a question that I dread answering whenever someone asks me, so instead of having an existential crisis about my own future, I'll instead look at the five-year outlook of teams around the NBA, and determine which five are set up the worst in their respective five-year plans.

Whether that be for lack of quality players, cap space, front office or ownership, the teams below project to be in a pretty bad spot over the next five years. It's no surprise that most of the teams on this list are in the Eastern Conference, where a handful of squads have failed year-after-year to stack up to teams in the West. 

Some of these franchises are in the midst of a rebuild, which isn't necessarily a bad thing. They're just trying to find themselves in this crazy thing called life, which is something a recently graduated college senior would say. Other teams are teetering between being mediocre and having everything crash and burn, like when you realize you actually hate the career path you've chosen but don't want to admit it. In reality, it's just prolonging the inevitable that you need to hit the reset button and start from scratch. 

First, though, here are some honorable mentions of teams that didn't quite make the top five, but could find themselves there if things don't go right.

Honorable mentions

Rockets: Let me paint you a picture of Houston's next few years: In the short-term -- like next season -- the Rockets don't have many moves they can make to improve this current roster because of the gobs of money being swallowed up by both James Harden and Russell Westbrook's contracts. That means this team will likely be running it back next season, which could go two ways. Either new head coach Stephen Silas gets this team over the hump of not getting to the Finals, or they fizzle out in the second round.

If the latter happens, then Houston is left with some really tough decisions to make. Tanking isn't exactly an option, because Houston owes five first-round picks in the next six years, and three second-round picks, making it incredibly difficult for the Rockets to add top-tier young players in the draft. So, that leaves Houston with the option of hitting the reset button entirely, which would include trading James Harden and Russell Westbrook and starting from scratch. The pieces they'd get in return for both players would replenish some of their draft capital, but if Houston gets to this point, then the future for them is incredibly bleak. 

Bulls: If Chicago didn't clean house over the past few months they would certainly be in the bottom five. But, hiring Billy Donovan to take over for Jim Boylen as head coach, and snagging Arturas Karnisovas and Marc Eversley to take over in the front office signals that this team may be turning the corner. So, it's simply too early to tell what this team can become under an entirely new regime. With a core of Zach LaVine, Lauri Markkanen, Wendell Carter Jr. and Coby White perhaps Donovan can unlock the potential of this squad. The ruling is still out on the Bulls, but they aren't exactly out of the woods just yet.

Spurs: The contracts of DeMar DeRozan and LaMarcus Aldridge make it difficult for San Antonio to enter a full rebuild, which is entirely necessary, but they do have promising young players in Dejounte Murray, Derrick White and Lonnie Walker to work with going forward. Not to mention that San Antonio always has a way to prove everyone wrong when we've counted them out. I wouldn't be surprised if this team was able to turn their future around with a couple offseason moves or savvy draft picks.

With the honorable mentions out of the way, here are the five teams with the grimmest five-year plans in the league.

5. Washington Wizards

In the immediate future for the Wizards, there is a world in which John Wall returns to All-Star form, the Wizards are able to re-sign Davis Bertans, and Bradley Beal builds upon his career year from a season ago. That could result in a couple of playoff berths for Washington in the next couple of years, and some fears about this team's future would be suppressed...for the time being.

However, there is also the very real possibility that Wall is a shell of his former self, or his return stifles Beal, which leads to minimal success for the Wizards. Beal already admitted that he signed a short-term deal in order to make himself available on the trade market IF the Wizards don't start winning games. That is not what you want to hear from one of your franchise cornerstones.

If Beal requests a trade, it would yield an attractive return package for the Wizards. But what if they don't trade him, and instead he decides to opt-out of his $37 million player option in 2022 and sign elsewhere, leaving Washington with nothing in return. That's a terrifying thought for the Wizards, and something that this team will have to think about as it tries to get back on track over the next few years.

The other negative is if Wall can't perform up to expectations and the Wizards can't unload his bloated contract, where he's set to make $47 million in 2022. He'll be 32 by the time his player option comes up, and the last three years of his career where he's been saddled with injuries doesn't exactly make him a prime trade target. Washington better hope the Beal-Wall tandem works, because if it doesn't then this team could be in for another lengthy rebuild.  

Also five years from now, Rui Hachimura will be 26 years old, and while he put together an impressive rookie season (13.5 points, 6.1 rebounds), he hasn't shown the ability to be a franchise piece. He could develop into a solid role player, and down the line, if Beal is traded, he could pair well with whatever they get in return, but right now there's just so much uncertainty around Washington's future.

4. New York Knicks

The Knicks are like when a new iPhone gets released. There might be some new updates and features to make you believe that this is really different, but under all the shine and new color options, it's still the same phone, and jokes on you because you just shelled out $1,000 for something slightly different but mostly the same. For New York, the new updates were bringing in Tom Thibodeau as coach and Leon Rose as president of the team, and while we don't want to write both of them off already, it's kind of hard not to when you consider the Knicks history over the past two decades, especially when James Dolan still owns the franchise.

Right now New York is at a crossroads, and the path they take could determine their future for the next five years. The Knicks are reportedly willing to take on bad contracts in exchange for assets, which would be the smart decision to make. New York is expected to have a wealth of cap space and since this team isn't going to be contending for a playoff spot any time soon, taking on hefty contracts that come attached to valuable assets would stockpile their arsenal even more for future moves or potential draft picks.

The next five years should be spent developing young guys like RJ Barrett and Mitchell Robinson, using their picks to draft quality players and make trades that land them assets, because at the end of it all this franchise could actually be in a good place.

But, the Knicks are the Knicks and they just can't get out of their own way. New York has been attached to names like Westbrook, Chris Paul, Victor Oladipo and even a reunion with Carmelo Anthony, showing that once again, this franchise doesn't want to put the time and effort into actually rebuilding and would rather sell off valuable assets for a big name. Adding any one of those stars would surely put fans in the seats at Madison Square Garden -- whenever that can happen again -- but what they would need to give up to get those players, especially when all of those names have serious injury concerns, isn't worth it right now. 

Taking on aging All-Stars who will take up a significant amount of cap space would just put a bandage over the issue that the Knicks need to rebuild their culture from within and actually develop the young players they have. 

History tells us that the Knicks will make the wrong decision and begin star chasing when they are ill-prepared to do so. Perhaps Rose changes that reputation, but for now, with what we know about this team, it's hard to envision a world in which they actually make a move with some foresight. So for now, the future is kind of foggy for the Knicks, but not a total disaster. 

3. Charlotte Hornets

Despite inspiring performances from Devonte Graham and PJ Washington this season in Charlotte, their track record doesn't suggest this team has any sort of quality five-year plan in mind. Take for instance the fact that instead of trying to trade Kemba Walker to get pieces in return, they just let him walk to Boston for nothing. Imagine what the Hornets could've gotten in return from Boston had they executed a sign-and-trade, or with any other team for that matter. Their future would likely look a lot brighter right now.

As great as Graham was last season, let's not give the Hornets too much credit for his success. He played just 14 minutes his rookie season, and instead of seeing what they had with him after Walker left, they gave Terry Rozier $56 million just to find out that Graham should be their starting point guard. 

Charlotte owns all of its future first-round picks in the next six drafts, but since landing Kemba Walker with their No. 1 pick in the 2011 draft, they've drafted in the lottery seven times in the last eight years and haven't hit on any of them, aside from maybe Washington, but it's still too early to tell if he'll become a valuable player. Then, when they actually did draft a potential star in Shai Gilgeous-Alexander with the 11th pick overall in the 2018 NBA Draft, they traded him to the Clippers for Miles Bridges, who doesn't project to be better than SGA. 

The Hornets will be getting off Nicolas Batum's disastrous contract in 2021, giving them even more cap space to work with in the future, but Charlotte isn't exactly a free agency destination. If the front office couldn't convince stars to play alongside All-Star guard Kemba Walker during his tenure there, what makes them think they could reel in a big fish with a squad of role players who are all under the age of 25.

Unless Graham, Washington or Bridges turns out to be a bonafide star, the Hornets look to be toiling away in the lottery for the next few years. Which, again, wouldn't be an issue if they could evaluate talent well. 

2. Cleveland Cavaliers

The next five years aren't looking too great in Cleveland. First, there's the Andre Drummond conundrum. After trading for the All-Star big man in February, the two sides were going to work out a contract extension. However, recent reports suggest that the two sides aren't close to an agreement, and it's not even a certainty that Drummond opts-in on his $28.8 million player option for next season. 

Then there's Kevin Love. The fact that Love is still on this roster is actually mind-blowing, considering the longer the Cavs wait to trade him the more deflated his stock is going to be. Especially when you factor in that he's still owed $91.5 million over three years and will be 35 years old when his contract expires.

The Cavaliers also have to figure out what to do with Tristan Thompson, who Cleveland failed to trade at the deadline back in February, and is now an unrestricted free agent. The Cavs could work out a sign-and-trade with Thompson, but the return might not be what they had in mind. Cleveland could also get something for versatile defender Larry Nance Jr., but it likely won't move the needle much either.

These are just things Cleveland has to consider in its immediate future. Looking even further ahead at its younger players, there are still many questions that remain.

Their backcourt, made up of Collin Sexton and Darius Garland, doesn't exhibit star quality, and they would be incredibly outmatched on defense against bigger teams. But Sexton's rookie scale extension is right around the corner in 2022, and it wouldn't make sense for them to move on from him so early. The same goes for Garland, too, when he's eligible in 2023. 

That means that the Cavaliers could be locked into big contracts with both players, neither of whom they are certain can fit alongside each other or can be stars in this league. By that time, the Cavs' cap space will be swallowed up by Sexton and Garland's contracts, and if neither can show potential to make a leap in the NBA, they won't be valuable trade assets either.

Cleveland, though, does own all of its future first-round picks, so just by the sheer fact that they'll likely be in the lottery for the next five years, they could be gifted with yet another No. 1 overall pick. However, the Cavs have been in that position before and have failed to build around their stars during the early years of LeBron as well as the first three years of Kyrie Irving's career. In fact, if it weren't for LeBron deciding he wanted to come back to the Cavs to win a title, Cleveland might still be in a championship drought.

  1. Detroit Pistons

Newly hired general manager Troy Weaver has some tough decisions to make in the coming years. In the short-term, the Pistons have an injury-riddled, aging Blake Griffin and one more year of the also injury-riddled Derrick Rose. If those two are healthy, though, that should keep Detroit somewhat competitive next season. However, that's not ideal when this team should be trying to secure one of the top picks in the 2021 NBA Draft and go into full rebuild mode.

The longer the Pistons are middling in mediocrity, the longer their rebuild will take, and seeing as Griffin and Rose are both on the wrong side of 30 with a lengthy list of injuries, neither of them should be in Detroit's long-term plans. 

In terms of assets, they own all of their future first-round picks, but in terms of young talent on this team, it's very minimal. Christian Wood is perhaps the best prospect on the team, but he's set to become an unrestricted free agent this offseason. If he gets too pricey, then Detroit may have to let him walk, otherwise, they'd be overpaying a player on a team that isn't expected to win many games.

The Pistons, like the Knicks, are armed with a wealth of cap space and are in the position to take on bad contracts with assets attached to them in order to rack up draft picks or promising young players. Also, like the Knicks, they can't get persuaded by the enormous amount of cap space they're projected to have and use it on names like Fred VanVleet who they could absolutely afford. Yes, VanVleet would significantly improve Detroit's backcourt, but what else do you put around him to make this team competitive after Blake Griffin's contract comes off the books in two years? Unlike New York, Detroit isn't a city that's attracting any big names, so the most viable way to rebuild this franchise is through the draft and trades that yield young players with upside. 

The issue, though, is that Detroit hasn't been great at evaluating talent. Maybe Weaver, who has a sterling record coming from Oklahoma City, could change that, but as it stands now, the Pistons have the grimmest five-year plan in the league.