The two met discreetly for approximately one hour in Allen's office at Moda Center before hosting the Indiana Pacers on Thursday, sources said. It was the first home game Allen attended in 2018.
Lillard, who will turn 28 on July 15, requested the meeting in part to reaffirm his commitment to the only professional franchise he has suited up for, but also to gain assurances that the organization was just as devoted to expeditiously crafting a title-contending team, sources said.
According to sources, the meeting was held without knowledge of anyone else in the organization. Allen notified the Trail Blazers' basketball operations and business branch afterward.
In the weeks leading up to the meeting, Allen feared Lillard would request a trade, sources said, but a trade request was not made. The two-time All-Star made it clear, though, that he has championship aspirations and wanted to fulfill those lofty goals during the remaining years of his prime window.
Portland, winner of three of its past four, is 25-22 and seventh in the Western Conference standings. The 2012-13 Rookie of the Year has led his team to the playoffs in each of the past four seasons but has yet to advance past the second round.
It's not unprecedented for Allen to meet with marquee players of his franchise. He is also the owner of the Seattle Seahawks and frequently has sit-downs with key players, a source said.
This was the first time Lillard and Allen have spoken in such a capacity, however. The meeting, which sources described as a productive, open forum to share opinions and express concerns, could also lead to more sit-downs in the future.
During the gathering, Allen also sought answers.
Allen acknowledged the roster imbalance but questioned why the team had suffered through an inconsistent first half. Lillard issued a heartfelt vote of confidence for head coach Terry Stotts, sources said.
They also discussed players to target. The New York Times' Marc Stein recently reported that the Trail Blazers are one of the teams trying to engage in trade talks with the LA Clippers for big man DeAndre Jordan, but the Clippers haven't had any serious offers.
In addition, Lillard sought an explanation from Allen as to why Will Barton was traded to Denver in February 2015, sources said. Lillard made it known he didn't agree with the move. Barton is a penetrating, spot-up shooter -- the type of player Portland could use on the wing.
Three years ago, the Trail Blazers were under enormous pressure to prove to LaMarcus Aldridge that they were all-in on acquiring proven talent to help make a championship run. The power forward was an unrestricted free agent at the end of the 2014-15 season and ended up signing with the San Antonio Spurs.
The 3-point ball is essential in today's NBA game, and it's an element the team lacks. Portland is one of the lower-tier 3-point shooting teams, ranked 19th in the league in makes (9.8) and 22nd in attempts (26.1). Lillard and CJ McCollum account for 50 percent of the team's made 3s this season, the second-highest duo percentage in the league. Only Stephen Curry and Klay Thompson of the Golden State Warriors combine for a higher percentage of their team's 3s at 53 percent, and the defending champs are equipped with personnel who dominate in other departments. With a lack of threats in Portland, opposing defenses load up on Lillard from pick-and-roll traps to all-out ball denials in an effort to force others to beat them.
The Trail Blazers' identity has fluctuated to the defensive end with a superior 104.2 defensive rating that is seventh in the league.
Portland currently has the fifth-largest payroll in the league at around $123 million, largely due to the summer of 2016, when the NBA's $24 billion television-revenue deal kicked in.
Evan Turner, Moe Harkless and Meyers Leonard are three of the five highest-paid players in Portland. Turner signed for four years and $70 million, Harkless re-signed at four years, $40 million, and Leonard re-upped for four years, $41 million. But Turner has drastically underperformed, while Harkless and Leonard are out of the rotation altogether.
Furthermore, the contracts of Andrew Nicholson ($2.8 million annually), Anderson Varejao ($1.9 million annually) and Festus Ezeli ($333,333 annually) are stretched out to 2024, 2021 and 2020, respectively.
The team did manage to unload Allen Crabbe's four-year, $75 million contract after trading him last summer to the Brooklyn Nets, the very team that extended the guard the offer sheet before Portland matched. With that move, the Trail Blazers are currently $2.8 million above the luxury tax threshold and have a current luxury tax bill of $4.3 million, according to ESPN's Bobby Marks.
Still, the roster is filled with position redundancy and minimal attractive assets. Aside from Lillard, McCollum and at times center Jusuf Nurkic, players have struggled to carve out a productive, consistent niche.
Lillard desperately yearns to bring a championship to Portland, which is why he inquired about the organization's plan of attack to accelerate the process. He has four years remaining on a deal that owes him $115 million.
On Monday, Lillard was named the Week 14 Western Conference Player of the Week after leading his team to a 3-0 record and averaging 29.3 points while shooting 53 percent from the field to go with 8.0 assists.