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Looking toward the future can be tough on NBA fans, especially those following a veteran team with legitimate aspirations of contention. But as losses mount, frustration boils and the play-in tournament beckons, it's time for Rip City to think beyond an increasingly unlikely postseason run for the Trail Blazers.

Neil Olshey and Portland's front office have several important decisions on their plate this offseason, including how to deal with Zach Collins' restricted free agency, whether to offer Anfernee Simons a lucrative contract extension and the status of Carmelo Anthony. Obviously, the Blazers' likelihood of living up to internal and external expectations are fading fast. How they finish out the season will go a long way toward informing Olshey's approach to answering the questions above.

The fate of Norman Powell, though, stands apart from that of other teammates with uncertain futures. Portland played its hand by trading for Powell at the deadline, knowing full well he's certain to opt out of his current contract for a bigger, long-term payday in free agency. The cash-strapped Blazers, remember can't replace Powell's salary slot if he chooses to sign elsewhere.

Portland, basically, must pony up the dough for Powell or risk losing him for nothing – an especially bleak possibility considering the Blazers would've owned match rights on Gary Trent Jr. in restricted free agnecy.

The problem isn't just that Portland, at least by record, has played its worst basketball of the season since Powell arrived. This summer's free agency class is weaker than expected, too, in wake of multiple stars signing mega extensions. 

Powell, it turns out, might be the best wing on the market, and according to Bleacher Reports' Jake Fischer, a long-sleeping giant with hordes of cap space could make him a target. Tom Thibodeau and the New York Knicks are apparently one of the many teams that "covet" Powell in free agency.

Thibodeau also covets Trail Blazers swingman Norman Powell, who has an $11.6 million player option in 2021-22, sources said.

The only carrot Portland can put in front of Powell that New York and other suitors can't is a fifth year on his upcoming contract. Turning 28 years old in a few weeks, Powell would probably prefer a four-year deal anyway, affording him a better chance to earn another pricey, multi-year deal before he hits his mid-thirties.

Maybe more important: Why would a player like Powell willingly tie himself to the Blazers' wayward – and potentially sinking – ship for his prime, irrespective of contract length?

Portland, as detailed by The Athletic's Jason Quick, has gone above and beyond to make Powell comfortable since his arrival. The organization even shuttled his Pomeranian Huskies across the country to his rental home in Lake Oswego, with toy-filled dogbeds awaiting them. 

The Blazers know full well how little time Powell has to acclimate to the team and his surroundings before free agency, and is leaving no stone unturned as a result.

“The first step to getting a ‘yes’ on a contract is getting a ‘yes’ on the market and town, so we want to show the best possible version of ourselves,” Olshey said. “We hope he wants to be here, and if he doesn’t, then it won’t be for lack of information.”

The numbers don't paint nearly as depressing a portrait of Portland's play with Powell in the fold as wins and losses, either. The Blazers' +0.9 net rating since Powell's debut on March 26th, per NBA.com/stats, is more than a full point better than their season-long mark. 

Skepticism about the postseason viability of Portland's three-guard lineup remains warranted until proven otherwise, but those groups aren't the source of its ongoing struggles. Powell, Damian Lillard and C.J. McCollum boast a +16.4 net rating when they share the floor, best among all team trios over the last month, per NBA.com/stats.

It's inevitable that playing alongside Lillard and McCollum will keep Powell from shouldering an outsized offensive role, though. His usage is down three points compared to his career-high 23.5 percent with the Toronto Raptors. Powell has spoken fondly of Toronto's commitment to defense when asked by local reporters about the Blazers' porous performance on that end, too.

Would he have more playmaking responsibilities playing second fiddle to Julius Randle? That largely depends on the Knicks' belief in the developmental track of R.J. Barrett, but New York's emphasis on defense no doubt appeals to Powell considering his background with the Raptors.

The Knicks are a free agency boogeyman again. Most players love Thibodeau despite his grating, old-school style, and the lure of New York City speaks for itself. Madison Square Garden will always be the NBA's basketball mecca – just ask Zion Williamson. 

But the Blazers' straits are dire enough that they need not worry about specific competitors in free agency. Any destination other than Portland – where a coaching change could be the least of its offseason upheaval – might seem a better one for Powell if the differences in contracts he's offered are negligible. 

The Miami Heat and Dallas Mavericks, for instance, should have plenty of cash to throw at Powell. Needless to say, there's not much about his current situation that would make staying put more attractive to Powell than chasing championships with Jimmy Butler and Bam Adebayo or Luka Doncic.

Whether or not the Knicks come calling, Powell will have plenty of options as a free agent. The only thing worse than the Blazers failing to turn their season around? That supremely disappointing development getting compounded by it rendering Powell a half-season rental.

READ MORE: Damian Lillard Takes Blame For Blazers' Struggles