However, according to The Ringer's Kevin O'Connor, there have been "whispers in league circles" that Portland should explore breaking up its core. Per O'Connor, though, there has been no indication that the Trail Blazers would entertain that notion.
Portland's run of sustained success has coincided with the arrivals of Lillard and McCollum. From 2003-12, the Trail Blazers made the playoffs just three times and were one-and-done each time. Lillard was drafted sixth overall in 2012 and wound up winning the Rookie of the Year award.
Then, the Trail Blazers took McCollum 10th overall in 2013—and they haven't missed out on the postseason since.
Lillard has been named to three All-Star teams during that time, and McCollum has proven to be a capable sidekick. Portland has gone 239-171 over the past five seasons, topping out at 54 wins during McCollum's rookie campaign.
There is no question that the Trail Blazers have been one of the best regular-season teams during the Lillard-McCollum era. On the other hand, they have not advanced past the second round during that span. They have lost 10 consecutive playoff games over the past three years, having been swept by the DeMarcus Cousins-less New Orleans Pelicans this year despite being seeded third.
Chris Haynes, then with ESPN, reported back in January that Lillard met with Trail Blazers owner Paul Allen (who died Monday) for an hour to discuss the franchise's direction. No trade request was made at the time.
McCollum made it clear on ESPN's First Take in May that he believes the Trail Blazers should keep the core together:
Portland can keep Lillard and McCollum together for years to come if it so chooses. Lillard is signed through the 2020-21 season after agreeing to a max extension in 2015, and McCollum still has three years remaining on his deal.
If the Trail Blazers are unable to take the next step in the postseason at some point, though, they may have tough decisions to make.