The Boston Celtics acquired Anfernee Simons in a one-for-one swap for Jrue Holiday last summer. However, Simons was immediately a trade candidate in Boston, as the motivation behind the deal was largely financial.
Boston was able to duck the second apron thanks to Brad Stevens' strategic trades, but they never genuinely viewed Simons as a long-term part of their core. There were legitimate concerns surrounding his expiring contract and defensive limitations as an undersized guard -- the same reasons the Portland Trail Blazers ultimately sent him away.
In retrospect, the Celtics clearly never should've traded Simons away.
Celtics should regret trading away Anfernee Simons
He had a slow start in Boston, but was finding his rhythm and settling into his sixth man role leading up to February's trade deadline. Despite the momentum, Boston decided to ship Simons to the Chicago Bulls in exchange for a 35-year-old Nikola Vucevic (swapping second-round picks in the process).
Blazers fans knew this was a downgrade for the Celtics, given how electric a microwave scorer and combo guard Simons has proven to be in Portland.
It immediately justified Portland's controversial decision to trade for Holiday, given the low value Boston received for Simons. But it was such a low return to the point where the Celtics would've been much better off simply holding onto Simons, despite his limitations and contract concerns.
That was apparent throughout the second half of the season, but particularly on the highest stage in Boston's Game 7 home loss to the Philadelphia 76ers.
Vucevic averaged 19 minutes per game through the first six games of the first-round series. But facing the highest stakes in the sport with a Game 7 on the line, head coach Joe Mazzulla elected to start Luka Garza. Predictably, both Garza and Neemias Queta got into foul trouble with their matchup against the superior Joel Embiid, who finished with a game-high 34 points along with 12 rebounds and six assists. Garza recorded a goose egg in just nine minutes of play, yet Mazzulla still didn't trust Vucevic enough to play him.
The lack of frontcourt solutions for Boston has been a problem all season. In what was viewed to be a gap year, they still managed to exceed expectations with a 56-20 record. That was largely due to how well Mazzulla's coaching style aligned with Boston's roster as a three-point-heavy team. The Celtics lost some of that strength when they traded Simons, who is quietly one of the best three-point shooters in the league.
We saw Boston's offense stall on multiple occasions throughout this win-or-go-home contest, and couldn't help but wonder if this would've been a different outcome had they not shipped Simons elsewhere.
It seemed like they were already set on that decision since acquiring him from Portland, and they continued to follow through on it at the deadline despite Simons proving he fit in Boston. Now, the Celtics are left to wonder what could've been had they had more offensive production. Blazers fans saw this outcome coming after witnessing the impact Simons has had on Portland's offense in the past.
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