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Will Anfernee Simons or Jerami Grant Last Longer with the Blazers?

The transitioning Blazers are in a state of flux. Which of the two veterans is moved first?

Portland Trail Blazers v Phoenix Suns Photo by Kate Frese/NBAE via Getty Images

Assuming Damian Lillard is moved over the next few months, Anfernee Simons and Jerami Grant are now the Portland Trail Blazers’ on-court leaders. Rookie point guard Scoot Henderson may usurp them at some point but without playing an actual NBA game, you’d have to imagine Simons and Grant are currently in charge.

Simons is tied to the Blazers for another three years and more than $77 million and Grant signed a five-year, $160 million deal in July to remain in the city if his birth.

While Grant is five years Simons’ senior, both players share a similar league-wide status. Neither have made an All Star debut but could very well be in the discussion over the next few years.

Around them are three relative veterans in Jusuf Nurkic, Matisse Thybulle and Nassir Little to go with a list of inexperienced young names with potential to burn and time to prove it.

Regardless of what General Manager Joe Cronin brings back in a Lillard deal, this team will be young and bad for a while, opening up questions about the future of the duo.

Grant is arguably in his prime and, as such, could soon be looking outside of Oregon. Simons is edging closer to this stage and faces a tricky situation in Portland with Cronin using high draft picks to bring in guards Henderson and Shaedon Sharpe over the past 15 months.

But which one of the two remains a Blazer longer?

Anfernee Simons

Post-lottery and pre-draft reports suggested Simons was being dangled along with the third pick in exchange for veteran talent to help a Lillard-led Blazers contend.

However, with Henderson’s selection prompting Lillard’s request for a change of scenery, Simons’ place in Portland made a little more sense, even with the bottleneck at the guard positions.

But said bottleneck will need to be resolved eventually, probably when the team is more focused on winning games. When that is depends on the speed at which the Henderson-Sharpe partnership matures.

Despite his facilitating ability still a work in progress, Simons is probably best played at point guard given his lack of size and defensive prowess to match up against bigger guards.

Unfortunately for Simons, once Lillard is gone, Henderson with all his potential and hype looks set to become the franchise’s next lead guard. Simons will subsequently continue as starting shooting guard.

The 24-year-old’s trade value is difficult to gauge. His lack of defense instantly reduces his list of potential suitors. However, his shooting, shot creation and facilitating potential are attractive attributes. Simons’ contract is perfectly fine for the level of player he is and might actually be looked upon as team friendly by its end.

Franchises that might have interest in Simons are those looking to take a gamble on a young athletic guy with point guard potential. I’m talking about the Toronto Raptors, Brooklyn Nets, Orlando Magic, Minnesota Timberwolves, Utah Jazz and San Antonio Spurs.

Jerami Grant

These are 29-year-old Grant’s years to make his biggest impact on the game. Some may argue that it’s unfair to expect him to toil away his best years on one of the worst team’s in the league, an experience he’s already lived through as a member of the Detroit Pistons.

Grant’s decision to re-sign with the Blazers was fiscally prudent given that Cronin could offer him that fifth year when others couldn't. But now that pen has been put to paper, he’s well within his rights to ask for a new team — particularly following the Lillard trade request — after he’s legally able to be moved in January.

Once Lillard departs, Grant will own the Blazers’ most expensive contract at roughly $32 million a year. Not a ridiculous number for a player of his ability and physical attributes, especially with the salary cap set to rise significantly in coming years.

Cronin’s dilemma with Grant is less about his place in the rotation or the money being paid and more about the forward’s drive to enjoy real team success at this stage of his career.

While Grant did talk up the Portland front office at July's press conference I wonder how much of it was lip service for the guy who just gave him $160 million.

“Joe is moving in the right direction, and he’s going to figure out what we can do to still be a winning team.”

If Grant does want out, the Blazers can decide to hold off until the right deal comes along. But they also may not have the appetite for another standoff given the current Lillard predicament.

No doubt, they’d prefer Grant to stay, especially given the roster currently includes only rookies and sophomores able to play the power forward position. I’m not worried about his money, rebuilding teams need a couple of contracts of significance, if only to get to the salary floor.

As far as Grant’s trade market is concerned, the length and size of his deal are a drawback, but not so bad that they eradicate all interest. Contending NBA teams are always in need of long, rangy wings who can defend, shoot and make plays in a pinch.

Grant finished in the 79th percentile, among forwards, in points per shot attempt last season (121.8). He was also in the 84th percentile in blocks and 82nd percentile from three, including 88th percentile from above the break. Ideally, he boosts his rebounding numbers as well.

Potential Grant suitors include the Los Angeles Lakers, Los Angeles Clippers, New York Knicks, Boston Celtics, Dallas Mavericks, Miami Heat, Oklahoma City Thunder and the Chicago Bulls.


Don’t be surprised if Cronin moves one or both of Simons and Grant for young players and draft picks at some stage in the next 12-to-24 months.

I’m as big an Anfernee Simons fan as anybody. But if Henderson and Sharpe show real development through the first three months of the season, I could definitely see the Florida product moved as early as February's deadline to better balance the roster.

As for Jerami Grant, I'm 99.9 percent certain he doesn't serve out all five years of his deal in Portland. Whether it's one year or two remains to be seen but I think he's on the team longer than Simons because of positional need — even if Grant does ask out. Cronin should wait for the right deal to eventuate.

If all goes to plan and the Henderson-Sharpe combination flourishes sooner than later, I’d expect Simons to be gone by the trade deadline.