Jason Kidd

Trail Blazers star Damian Lillard will become eligible for a two-year, $106MM extension during the 2022 offseason. That extension – which Lillard wants to lock in, per ESPN’s Adrian Wojnarowski – would begin in 2025/26 and would cover his age-35 and age-36 seasons.

Lillard and his agent need Portland’s next permanent general manager to sell team ownership on offering that super-max extension, according to Wojnarowski, who hears that the guard’s camp had concerns about Neil Olshey‘s willingness to recommend such an offer to Jody Allen. Chris Mannix of SI.com also hears that Olshey wasn’t sold on tacking two more years (at $51MM and $55MM) onto Lillard’s deal.

Although Lillard and his camp will be motivated to help the Blazers find a GM who is receptive to offering that extension, most of the top-level candidates who figure to draw interest from Portland aren’t enthusiastic about making that offer, says Wojnarowski. In fact, some of those potential candidates told Woj that they’d be more interested in the Blazers’ job if they could trade Lillard and rebuild, rather than extending the six-time All-Star.

According to Wojnarowski, Lillard’s camp is “privately selling the idea” of the Blazers trading some of their current players and continuing to build around Dame (on a new extension). However, candidates for the permanent general manager job in Portland believe they’ll need to sell themselves to team ownership, not to Lillard and his camp.

While it remains possible Lillard’s group will have some input in the GM choice, Wojnarowski suggests they’ve been “thwarted on several leverage plays” this year, including their preference for Jason Kidd as Terry Stotts‘ replacement and their desire to trade for Ben Simmons.

Here are several more rumors out of Portland:

• The Blazers haven’t begun reaching out to potential candidates for the permanent GM job, according to Jake Fischer of Bleacher Report, who hears that there’s no concrete list of contenders yet beyond interim GM Joe Cronin. The organization is still deciding whether to hire a firm to research and recommend candidates, per Wojnarowski.
• The Pelicans offered Jrue Holiday to Portland in 2020 in exchange for CJ McCollum and three first-round picks, according to Jason Quick of The Athletic. A deal involving McCollum remains possible, but the Blazers are considered more likely to move Jusuf Nurkic and/or Robert Covington, says Fischer, adding that the team is “presently known to be down on both players.”
• Lillard has expressed interest since the 2020 offseason in a handful of defensively-minded wings, per Fischer. Besides Simmons, Lillard has also shown interest in playing with Jaylen Brown and Aaron Gordon, sources tell Bleacher Report.
• According to Fischer, Lillard’s lower abdominal tendinopathy is an injury that has bothered him off and on for years. The All-NBA guard even considered surgery this past offseason to address the issue, Fischer adds.
• There are several teams with interest in trading for Lillard, but three teams in that group told Wojnarowski they’d want to wait for the 31-year-old to request a trade before calling Portland, since the Blazers’ leverage would be reduced in that scenario. The Sixers have made an offer, but the Knicks haven’t, Wojnarowski adds. For his part, Lillard would have limited leverage to push for a specific landing spot if he asks out, since he still has three more years left on his current contract after 2021/22.
• Multiple league sources with knowledge of the situation tell Fischer that some Blazers players this season have been frustrated with Chauncey Billups‘ “coaching demeanor,” as well as his offensive system. In the latest Hoop Collective podcast, ESPN’s Brian Windhorst, Ohm Youngmisuk, and Ramona Shelburne discussed the fact that Billups’ tendency to call out players publicly may rub the current generation the wrong way.
• There have been whispers that Blazers owner Jody Allen might decide to sell her stake in the Blazers following the NBA’s next television agreement, says Fischer. If that’s the plan, there will be even more pressure on the team to make sure its next front office hire and big roster moves are the right ones.