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League insiders say Isaiah Thomas’ best chance of landing a major deal is with the Cavs

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A future in Cleveland could do wonders for I.T.’s bank account.

NBA: Cleveland Cavaliers at Orlando Magic Kim Klement-USA TODAY Sports

There are few storylines more intriguing for the 2017-2018 Cleveland Cavaliers than the saga of Isaiah Thomas. Thomas went from an MVP candidate on a team trying to establish legitimacy, to a potential x-factor on a championship contender. On top of the storylines on the court, there’s the looming pressure of what Thomas will command as a free agent this summer.

ESPN’s Brian Windhorst wrote a piece illustrating why the Cavs may make the most sense for Thomas as a free agent, regardless of what LeBron James does this summer. He also reports that league executives and agents believe Thomas’ best chance of landing a major deal is with the Cavs.

As he noted, the market has changed for older point guards like Thomas recently. While money is still available, similar players like Kyle Lowry, Jeff Teague, and George Hill didn’t get the term they expected. Plus in Thomas’ case, the teams that would have the cap space to make an offer at Thomas don’t have a need at point guard:

The Bulls have a budding star in Kris Dunn, the 76ers have Ben Simmons, the Mavericks have Dennis Smith Jr., the Hawks have Dennis Schroder, and the Lakers have Lonzo Ball. There are some options: Brooklyn, Phoenix and Indiana are possibilities, for example, though the Suns already traded Thomas once. It’s not inviting even if Thomas had no injury concerns, which he does with possible degenerative hip issues.

He continued to go into some of the intangible aspects of the situation that could lead to Thomas staying in Cleveland:

One, the Cavs will be under some pressure to retain him because he’s a prime asset from the Kyrie Irving trade. Though the Cavs made it clear behind the scenes that they saw the Nets’ pick as the primary carrot, the Nets’ stronger-than-expected play this season is threatening to push that pick deeper into the lottery. Currently, it is projected to be the ninth pick. A team, even a rebuilding team as the Cavs might be if James walks, cannot allow prime assets to leave for nothing.

Second, Gilbert loves underdogs like Thomas. He sees himself as an underdog, a self-made billionaire who went to Michigan State, not the Ivy League. In 2016, Gilbert was the driving force behind paying $2.4 million to buy a draft pick to take Kay Felder, an undersized point guard from Oakland University who attracted Gilbert because of his ability to overcome challenges. Felder didn’t make it with the Cavs, but Thomas is the embodiment of what the Cavs were dreaming of with Felder.

How Thomas finishes out this season, plus how he contributes against the Warriors will likely factor heavily into the deal he receives. But it’s interesting to examine what the predicted market looks like at this point and wonder how high the Cavs will have to go to retain him.

While I agree with the notion that asset management is important, I do think it would be unlikely that the Cavs would retain Thomas, if LeBron decided to leave. He was incredibly unhappy during his time in Sacramento and Phoenix. Now that he’s had a taste of winning, I doubt he would he would want to stay with a LeBron-less Cavs team without a serious overpay by Cleveland.

Ultimately this is putting the carriage ahead of the horse. We don’t know what the Cavs will look like after the trade deadline, where the Brooklyn pick will end up, or what LeBron will do. The main takeaway should be that if LeBron is staying and the franchise is still eyeing a championship in the short-term, they will be in a fairly good position to retain Thomas, should they choose to do so.