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Five big Damian Lillard trades we want to see the Portland Trail Blazers pursue

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Woj: Blazers nearing a 'moment of truth' with Damian Lillard (1:43)

Adrian Wojnarowski explains how Damian Lillard's desire for a contract extension could have long-term ramifications for the Blazers. (1:43)

As ESPN's Adrian Wojnarowski detailed on Tuesday, the situation in Portland is as tenuous as it has ever been during Damian Lillard's 10-year tenure with the Trail Blazers. The five-time All-Star has spent his entire NBA career in Portland, but one of the first questions facing a general manager to replace the recently fired Neil Olshey will be whether to give Lillard a big-money extension this offseason or to trade the superstar and rebuild around the return such a deal brings in.

With more than 100 free agents who signed this offseason becoming trade eligible next week, Portland's options in a trade are about to become more plentiful. A Lillard deal also could bring in the kind of draft haul that teams like Oklahoma City (for Paul George), New Orleans (for Jrue Holiday) and Houston (for James Harden) have been able to collect in recent years.

With that in mind, we asked our NBA experts to come up with potential moves the Blazers could make if the decision is made to end the Lillard era and start on a franchise reboot.