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Lillard camp keeps pressure on Trail Blazers, latest reports says re-signing not “sure thing”

Portland Trail Blazers v Los Angeles Lakers

LOS ANGELES, CALIFORNIA - DECEMBER 31: Damian Lillard #0 of the Portland Trail Blazers brings the ball up court during the first quarter against the Los Angeles Lakers at Arena on December 31, 2021 in Los Angeles, California. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Katelyn Mulcahy/Getty Images)

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The Portland Trail Blazers have traded for Jerami Grant, re-signed Anfrenee Simons, re-signed Jusuf Nurkic, picked up the guaranteed year for Josh Hart, and poached Gary Payton II away from the defending champs. Not a bad offseason in Portland.

Plus, they are offering Damian Lillard $100 million over two years to be the star of this team.

But Lillard and his camp want to keep the pressure up on the Trail Blazers, hence this sourced note from Sam Amick of The Athletic.

While it has been widely assumed Lillard will accept the two-year extension offer worth more than $100 million that is expected to come his way, sources say the Trail Blazers still needed to have a strong offseason to persuade Lillard to sign on through the 2026-27 campaign (when he’ll be 36). The deadline here isn’t until the start of the regular season, and I’m being told this is not a sure thing just yet.

There are moves Lillard — and Blazers fans — can question. For example, holding onto the No. 7 pick and using it to draft a raw player who will need time to develop in Shaedon Sharpe. The rookie has the tools to be special but didn’t play a minute at Kentucky and is years away — not the move for a win-now team trying to convince an almost 32-year-old superstar to sign up for a couple more years.

However, Lillard could not ask much more of Trail Blazers GM Joe Cronin. Given the tools and timeline he had to work with, this is a good job on a fast turnaround. These Trail Blazers are not contenders, but if Lillard is 100% back to being his vintage self this can be a playoff team and a tough out.

Good luck finding anyone around the league who thinks Lillard is going to leave that money on the table — the time to look for a new home was when teams had money and flexibility, not after they spent it all over the last 24 hours. Lillard is going to grab that $100 million bag. However, if this team disappoints, he may ask to take that bag to a new franchise in the future.

For now, expect him to remain a Trail Blazer.