The Portland Paradox: Trade CJ McCollum or risk losing Damian Lillard

Portland Trail Blazers guards Damian Lillard and CJ McCollum are the NBA's longest-running backcourt pairing. When McCollum joined Lillard in the starting lineup to begin the 2015-16 season, two teams now anticipating their potential breakup — the Philadelphia 76ers and New York Knicks — started guards Isaiah Canaan, Hollis Thompson, Jose Calderon and Sasha Vujacic. Portland has stuck to its guns for that long.

No more tinkering around the edges. It's high time the Blazers trade Lillard or McCollum.

The duo survived seven-time All-Star big man LaMarcus Aldridge's exit and welcomed center Jusuf Nurkic at the 2017 trade deadline. More than 20 different forwards have since started with Lillard, McCollum and Nurkic, as longtime general manager Neil Olshey ultimately scrolled through a rolodex of limited returns.

That rotating cast has ranged from Wenyen Gabriel to Carmelo Anthony and included a number of quality role players, including the current pairing of Norman Powell and Robert Covington. We have seen enough to determine that it's not just an inability to identify a rising star at the league's most important position that has lowered Portland's ceiling below championship level. They have maximized their two small(ish) guards.

Blazers in top-to-bottom disarray

Following a monthlong investigation into Olshey's alleged role in fostering a hostile workplace, the Blazers fired the executive to end their nine-year partnership, replacing him in the interim with assistant Joe Cronin. This developed months after Olshey faced criticism for his hiring of first-time coach Chauncey Billups, who in 2000 settled a civil lawsuit with a woman who accused him and two other men of sexually assaulting her.

A second straight first-round playoff exit and unrest in Portland over the hiring of Billups led Lillard to strongly consider requesting a trade from the only NBA team he has known, but the superstar and his new coach found common ground in their championship aspirations, according to Yahoo Sports' Chris Haynes.

Just 24 games into their partnership, Billups is openly questioning his roster. Playing without Lillard, the Blazers followed Thursday's 114-83 loss to the 12th-place San Antonio Spurs with a 145-117 loss to the Boston Celtics on Saturday. Afterward, Billups unleashed on his team for a third time in as many weeks.

"I've never seen a team that needs its bench to inspire our starters," said Billups, whose team ranks dead last in the league in defensive rating. "That s*** is crazy to me. It's supposed to be the other way around."

Lillard reportedly is also weary of Portland's 11-13 start to the season, per The Athletic's Shams Charania and Sam Amick. Except, this time Lillard is reportedly considering a trade that would send McCollum packing.

Report: Damian Lillard 'would like to play with' Ben Simmons

The Athletic cited multiple sources in reporting that Lillard "would like to play with" Sixers star Ben Simmons — a deal that would ship McCollum to Philadelphia in return. According to Charania and Amick, 76ers executive Daryl Morey requested McCollum, three first-round picks and three first-round pick swaps in exchange for Simmons, while Olshey countered with McCollum, a first-round pick and either Nassir Little or Anfernee Simons. Meeting somewhere in the middle seems like a logical step forward for both teams.

Unless Morey is willing to wait for Lillard to ask off the Blazers. What other perceived upgrades are out there in exchange for McCollum, who is owed $100 million over the next three seasons? The All-Star trade market is awfully dry. Christian Wood may not be long for the Houston Rockets. Myles Turner or Domantas Sabonis might be had from the Indiana Pacers. Any of those moves likely requires moving Nurkic, too, and that still feels like shuffling less than a full deck. Lillard and Simmons are no guarantee to succeed, either.

Beyond trading McCollum and Nurkic in multi-team deals that returned Simmons and Wood — a pair of still-improving rising stars who would address some of Portland's potential spacing and defensive concerns — it's hard to imagine too many scenarios that could lift the Blazers' ceiling to Lillard's desired level. Olshey failed to develop his picks since landing Lillard and McCollum in back-to-back drafts, and one of the three first-rounders he traded for Covington and Larry Nance Jr. is still outstanding, complicating negotiations.

Blowing up the Blazers

In other words, the Blazers must also seriously consider the alternative: A full rebuild. Trade them all.

Lillard would fetch a massive haul, despite his own struggles with an abdominal strain that has hampered him since the Tokyo Olympics and cost him the past three games. He is one of the 75 greatest players ever and a top-10 active performer when healthy. Morey's Sixers are desperate for a star of Lillard's caliber, and the Knicks would almost certainly enter a bidding war to bring Dame Time to Madison Square Garden.

Parting with McCollum, Nurkic and other veterans would further restock Portland's dearth of young talent and draft assets, while also giving them a shot at the two most coveted players in 2022 — Seattle native Paolo Banchero and Gonzaga freshman Chet Holmgren. Suddenly, that is not such a bad restart, especially if Simmons is among the players coming back to the Blazers. It is at least worth having the conversation.

Only, who do the Blazers want leading that conversation? Blazers president of business operations Chris McGowan said in September that "the team's not for sale" by team owner Jody Allen, who inherited the franchise from her brother, Paul, in October 2018, but McGowan resigned in the midst of the investigation into Olshey to accept a similar role with the Detroit Red Wings, Detroit Tigers and Little Caesars Pizza.

Cronin was given the interim general manager title. Bulls GM Marc Eversley and Knicks GM Scott Perry are both candidates for the full-time position, according to Haynes. Who exactly will be responsible for hiring Olshey's replacement is a legitimate question, as is whether or not that is the person you want making the most important decision the franchise has faced since it began its run of eight straight playoff appearances.

Lillard has to be wondering both, which means Portland is in a race to decide how to build around its superstar or risk losing him amid top-down uncertainty. It is high time to trade McCollum, or blow up the entire roster before Lillard becomes eligible this summer for a two-year, $107 supermax extension that would keep him under contract through 2027, so the Blazers better start answering the hard questions now.

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Ben Rohrbach is a staff writer for Yahoo Sports. Have a tip? Email him at rohrbach_ben@yahoo.com or follow him on Twitter! Follow @brohrbach