This is the most important summer of Damian Lillard’s reign in Portland. For the past decade, the Portland Trail Blazers have been the Warriors’ little brother. Think Seth Curry and Steph Curry, but in franchise terms.
The comps between Damian Lillard and Steph Curry stir up the most fervent debates, but Portland has also struggled to unlock the ball movement (they’ve typically been among the league’s worst in passes and assists per game) or the defensive backbone that has defined Golden State’s success. This year’s NBA Finals features Golden State, the NBA’s second-best defense, against Boston, the NBA’s No. 1 defense.
Since bumping against their ceiling in 2019, the Blazers have finished the following seasons 28th, 29th and 29th in the defensive rating metric that measures points allowed per 100 possessions. After three years of futility, the Blazers are finally in a position to address their shortcomings. Yet, instead of surrounding Lillard with two-way defensive wings like Andrew Wiggins and versatile switchable bigs in the vein of Robert Williams, the Blazers are poised to double down on their all-world offense, bottom-barrel defensive strategy this offseason.
Last month, ESPN insider Brian Windhorst reported that the Blazers were actively involved in discussions around acquiring free-agent guard Zach LaVine. This week, The Ringer’s Kevin O’Connor reported that the Blazers are buzzing around LaVine and Wizards free agent Bradley Beal. Targeting longshot scorers seeking between $212 million to $250 million max contracts is a gamble that they have to make because the pair also represent their last chance to give Lillard a fighting chance in the West. LaVine or Beal would make Portland an exciting playoff team. Neither is enough to put them within earshot of the Finals right away. Both are perimeter defensive turnstiles. Beal shot 30 percent from distance this season, and LaVine is an explosive athlete with a history of knee problems.
However, that’s not the point. Portland is striving to put Lillard back in the playoff hunt and simultaneously keep Anfernee Simons, their point guard of the future. Moving CJ McCollum to New Orleans in a buzzer-beating deadline deal could have been an opportunity for a total reset. Portland is still owed a future first round pick from the McCollum trade, which became a 2025 first from the Bucks instead of a 2023 Pelicans first rounder after New Orleans escaped the lottery and burst into the playoffs as an 8-seed. Instead, the Blazers have tossed their impulse to begin a youth movement overboard in favor of a desperate rebuild on the fly.
Re-signing Simons, who is a restricted free agent and just turned 23 today, is equally high on Portland’s list of priorities as signing Beal or LaVine. Lillard’s injury allowed them to toss their coveted 2018 first-round pick into the fray as a starter. In 27 games, Simons averaged 23.4 points and 5.8 assists on 42 percent shooting from distance and proved to be the heir apparent at point guard. His emergence gave Portland the choice of accelerating a relaunch around a dynamic guard or pairing him with Lillard.
There’s a reason previous Blazers general manager Neil Olshey considered Simons the most gifted player he’d ever drafted. Simons thrived as a primary ballhandler, though, which means Lillard’s return will stuff Simons back into an uncomfortable off-ball role next season, albeit a more prominent one than he occupied before McCollum was shipped to Bourbon Street. Portland doing their due diligence on potential 2022 free agents is sensible, but it puts them in a precarious position. After clearing McCollum’s contract, they’ll have to renounce the rights to several other players and trade center Jusuf Nurkić if they want to free up the necessary cap room to sign a max-contract player and keep Simons in a Blazers uniform. Defensively, the Lillard and Simons pairing won’t be pretty, but it’s what Portland is selling their loyal star on. Things could get uglier on the defensive end if they’re forced to dump Nurkic to make room for Beal or Lavine. Portland can always trade that seventh pick, but that’s a high-wire act without a parachute which mortgages their future for a limited amount of short-term relief.
This offseason high-wire act has a parachute option. If Rip City’s offseason fizzles, general manager Joe Cronin can accept reality and trade Lillard for players or picks who fit Simons’ timeline. Lillard’s value on the trade market will only diminish as time progresses. Brooklyn secured a reservoir of talent and picks for a portly James Harden. Boston reached the Finals thanks in part to the haul of picks they stockpiled by trading Kevin Garnett and Ray Allen to Brooklyn in 2013. Right now it’s a seller’s market for Portland and Lillard, but they can’t sell each other blind hope forever. Lillard will be 32 next month and father time waits for no man.