Having lost Kevin Durant to the Golden State Warriors in free agency, the conference finalists are hoping to avoid a repeat situation in 12 months time as Westbrook approaches the same stage of his career.
The Thunder need around $8.7 million in cap space to offer Westbrook a max extension that would take his salary from its current $17.7 million to around $27.5 million just this year.
Having rescinded Waiters' qualifying offer, making him an unrestricted free agent, the Thunder had held on to his Bird Rights, meaning $12.8 million was spoken for. However, as Waiters heads to South Beach, it means OKC are more than $14 million under the cap limit.
The early signs in free agency were that Westbrook had no intention of re-signing with his current team, but it appears the Thunder are not willing to down without a fight. The question for the All-Star point guard is; what is he looking for? Is money or success a priority for him at this stage?
If it's money he's after then signing an extension at the Chesapeake Energy Arena would see him bring in more cash than waiting for his unrestricted free agency period to begin. However, the Thunder no longer appear to be a serious threat in the deep Western Conference.
Of course, there is the challenge of potentially leading the franchise to glory without Durant, but the fear factor surrounding the organisation disappeared with his move to the Bay. Westbrook has a big decision to make - it's clear what the Thunder want, now we have to wait and see what he really wants.