Does Simons Make Sense for Lillard’s Timeline?

I want to make this very clear: I hope Anfernee Simons becomes a perennial All-Star for the Trail Blazers. I hope he’s the next evolution of the Brandon Roy/Damian Lillard lineage. I hope we’re hanging his number from the Rose Garden rafters in 2038. I wish nothing but success for him.

BUT, general manager Neil Olshey’s decision to pick the 19-year old project from IMG Academy is a bit of a headscratcher, given Olshey’s pledge in April to bring in veteran talent that can help the Blazers get over the hump in the playoffs. At best, Simons will be ready to contribute in 3-4 seasons, right around the time that Damian Lillard’s contract is ending.

With this pick, Olshey may be threading the needle of trying to simultaneously convince Lillard the team can compete immediately, while also preparing for the future. The strategy is not necessarily a fatal misstep, but it is a risky decision on Olshey’s part.

Do the Timelines Match?

Heading into the draft the Blazers had four assets that could bring back significant positive value in trade relative to what is being sent out: 1) the Allen Crabbe trade exception, 2) CJ McCollum, 3) the No. 24 pick, and 4) Zach Collins. Collins is presumably off the table given Olshey’s affinity for the Gonzaga product, which now leaves the Blazers with McCollum and the TPE as potential trade chips to significantly improve the team.

By picking Simons the Blazers have lost the opportunity to package either of those assets with a draft pick, making the “get an impact veteran” goal ever so slightly more difficult to achieve. Again, this is not necessarily a fatal decision — heck it could be a great decision if Simons pans out — and Olshey could still work out a beneficial CJ trade or use for the TPE without a draft pick tacked on. But the short term reality is that the Simons selection does make win-now transactions slightly more difficult.

As for Simons, the importance of timelines are generally overstated in the NBA, but the Blazers do need to make some sign of measurable forward progress by the time Lillard’s contract is up for renewal in three years. Simons will almost certainly not be a meaningful contributor for the next two seasons meaning that the Blazers may be stuck selling Lillard on the “potential” of teaming up with Collins and Simons on the back end of his career with little tangible on-court evidence to back up the claim. That’s a tough sell.

Bottom Line

In a vacuum, selecting Simons does not make much sense for the Lillard-era Blazers and may be indicative of a team that’s struggling to manage its future and present simultaneously rather than delivering on the pledge to to do what is necessary to win now. That’s an extremely dangerous game to play and could ultimately sabotage the team both now and at the end of Lillard’s contract.

Olshey can still compensate for this by making aggressive moves in free agency, but after a non-descript draft night, fans will be forgiven if they start to worry that the apparently risk-averse Blazers plan to run back the same roster that was ignominiously swept out of the 2018 playoffs.