Last summer, a disgruntled All-Star forward requested a trade. A small-market team with a franchise-caliber point guard swooped in and unexpectedly acquired him, undeterred by persistent chatter about his interest in heading to Los Angeles as a free agent the following summer.

That worked out brilliantly for the Oklahoma City Thunder, who won Paul George over enough to have him re-sign for at least three more seasons.

Will the Portland Trail Blazers follow suit?

jimmy butler

On Wednesday, The Athletic's Shams Charania reported All-Star swingman Jimmy Butler has requested a trade from the Minnesota Timberwolves. According to ESPN's Adrian Wojnarowski, the Los Angeles Clippers, Brooklyn Nets and New York Knicks are atop Butler's list of preferred trade destinations, although “his list could expand based upon the Timberwolves' and rival teams' willingness to negotiate a trade for him.”

The Trail Blazers are notably absent from that list, which may deter them from getting involved in the bidding. But after a demoralizing first-round playoff sweep at the hands of the New Orleans Pelicans this past spring, a drastic shakeup may be just what the doctor ordered for Portland.

While both Damian Lillard and CJ McCollum are under contract through the 2020-21 season, Portland's long-term outlook appears bleak at the moment. The Blazers are well into luxury-tax territory this season, and they're already more than $10 million above the projected $109 million salary cap for 2019-20 as well. They have just $80.3 million in guaranteed salary on their books for the 2020-21 season, when the cap is projected to be $116 million, but their only four players under contract that year are Lillard, McCollum, Jusuf Nurkic and rookie guard Gary Trent Jr.

Damian Lillard, Blazers

Lillard reportedly met with team owner Paul Allen in January to “gather an understanding of the organization's direction,” according to ESPN.com's Chris Haynes. Though he stopped short of demanding a trade at the time, he requested the meeting “to gain assurances” that Portland was “devoted to expeditiously crafting a title-contending team.”

A first-round sweep likely wasn't what he had in mind.

Unless the Blazers strike gold with a mid-first-round pick (a la Giannis Antetokounmpo or Kawhi Leonard), they have two options moving forward: bank on internal improvement as they seek to avenge last season's dispiriting playoff loss, or embark upon a drastic shakeup. In April, The Ringer's Kevin O'Connor made the case for the latter approach, noting Portland needed to “create better roster balance and add stronger wing defenders who can shoot.”

CJ McCollum

Lo and behold, one such option—Butler—may soon become available.

With a number of other Western Conference contenders locked into an increasingly escalating arms race, the internal-improvement route isn't likely to work for Portland. But general manager Neil Olshey doesn't seem to be in a hurry to break Lillard and McCollum apart, either.

“This narrative that if you don’t win a championship then it’s not worth competing, that’s a false premise,” he told SB Nation's Paul Flannery in April. “There’s got to be an intrinsic joy of watching your team play well and compete. If it’s just about the end result and not about the journey, then what’s the point?”

Those comments hardly suggest that Olshey will consider shipping out McCollum in a prospective deal for Butler. But should he?

jimmy butler

It's fair to wonder whether a Blazers team built around Lillard and McCollum has a clear ceiling that falls short of a championship contender. Neither is a strong defender, which could prove fatal against the plethora of top-tier guards throughout the West. Though the pairing of Lillard and McCollum had a net rating of plus-4.8 during nearly 1,900 regular-season minutes, it got blown off the floor in the playoffs, posting a net rating of minus-12.7.

Thanks to an ill-advised spending splurge in the summer of 2016, the Blazers don't have many outs. They'd likely have to attach valuable assets—whether it's future draft picks or young prospects—to dump the likes of Evan Turner or Meyers Leonard on another team. Given Moe Harkless' steep drop-off last season, it's unlikely they'd be able to fetch much for him, either.

They can't trade newly re-signed center Jusuf Nurkic until mid-December, although a second-year breakout from Zach Collins could eventually render him dispensable. Al-Farouq Aminu is on an expiring contract just shy of $7 million, but he was their third-best player in the playoffs last season.

jimmy butler

If they're reluctant to blow apart the Lillard-McCollum backcourt, the Blazers do have another option. Since salary-cap space is effectively inconsequential for them over the next two seasons, they could instead attempt to flip one of their undesirable contracts for an equally bad one.

The Houston Rockets just went that route while dumping Ryan Anderson on the Phoenix Suns. Rather than coughing up a first-round pick to shed his deal, the Rockets took back the remaining two years and $30.3 million on Brandon Knight's contract, along with 2016 No. 8 overall pick Marquese Chriss.

Earlier this summer, the Oklahoma City Thunder embarked upon a similar approach with Carmelo Anthony, shipping him to the Atlanta Hawks in a three-team deal that netted them out-of-favor point guard Dennis Schroder.

Damian Lillard, CJ McCollum, Blazers

Look closely enough around the NBA, and it shouldn't be hard for the Blazers to find contracts that teams would like to flip. Atlanta Hawks swingman Kent Bazemore, Miami Heat center Hassan Whiteside and T-Wolves forward Andrew Wiggins are three such examples, but many more exist throughout the league. Perhaps a reunion with Nicolas Batum is in order? Maybe Orlando wants to escape from the final three years of Evan Fournier's deal? Would Toronto be willing to ditch lightly used reserve Norman Powell?

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All of those moves may effectively amount to shuffling deck chairs on the Titanic. None of them would make the Blazers more competitive in playoff series against elite Western Conference teams like the Golden State Warriors or Houston Rockets. Swinging for the fences on Butler may be their best hope in that regard.

Since McCollum is under contract for three more seasons, the Blazers should have leverage over the T-Wolves in trade talks. Though a straight-up Butler-for-McCollum swap works salary-wise, Portland should attempt to extract additional assets for incurring the risk of Butler leaving as a free agent next summer. Whether that means dumping one of its bad contracts or getting another useful piece such as Taj Gibson or Tyus Jones along with Butler, possibilities abound.

Jimmy Butler, Timberwolves

The best-case scenario for the Blazers would be acquiring Butler without giving up Lillard or McCollum, but other teams could easily top those offers. To get Butler, they'd all but certainly have to give up McCollum, which is undeniably risky given Butler's ability to walk in 2019.

If Olshey is content with treading water, Portland may decide standing pat is the prudent path. After all, another 45-win season and competition for a playoff spot should still put butts in seats. But if the Blazers collapse in the playoffs once again—or miss the postseason outright—they'll be one year closer to Lillard and McCollum's free agency, reducing the trade value of each.

Selling high on McCollum and swinging for the fences on Butler is a high-risk, high-reward play that could breathe new life into Portland.

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Unless otherwise noted, all stats via NBA.com or Basketball Reference. All salary information via Basketball Insiders.

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