If there's ever a time to chase a proven championship player for the Cleveland Cavaliers, it's now.
In a late night trade, the Boston Celtics dealt Jrue Holiday to the Portland Trail Blazers for Anfernee Simons alongside two second-round picks. The deal shed over $10 million for the Celtics as the recent champions seek to reshape their cap sheet in the wake of a devastating Jayson Tatum injury that will likely cost him an entire season.
This deal marks the second time Holiday was a member of the Trail Blazers, though he has never played a game for the franchise. When he joined Boston, he did so after a trade from the Milwaukee Bucks sent him to the Blazers for a few days before being rerouted to join a championship contender.
Holiday has built a reputation as one of the league's premier defensive guards and a tremendous veteran leader on offense. With a second trip to Portland, the potential for Holiday to join another franchise hoping to win now rather than staying put could be in play. If that happens, the Cavaliers cannot miss the opportunity to accomplish what the Bucks and Celtics did by trading for the final piece to orchestrate a Finals run.
Trading Jrue to Cleveland
With a $32.4 million price tag next season, Holiday could not only give the Cavs' backcourt grit and leadership but also help Cleveland manage the daunting second apron restrictions. In a trade for Jrue, the Cavaliers would have to include Darius Garland, trading their All-Star point guard for a veteran champion who likely fits the team's needs better.
In return for a young, upcoming point guard in Simons, the Blazers accepted an aging point guard and gave up two second-round picks in the process. This second deal offers a much greater package for Holiday, giving Portland an All-Star and refreshes their forfeited draft compensation.
While the Blazers may hesitate to add another guard to a stacked backcourt rotation, Garland has proven to be the spark plug to accelerate a rebuild into playoffs contention as he did with the Cavs in the 2021-22 season. He has only gotten better since then, and adding DG to Portland's ranks gives centers Donovan Clingan, Robert Williams III and DeAndre Ayton a skilled facilitator keen on feeding the post with timely and swift dishes down low.
According to Capsheets.com, the Blazers sit at roughly $181 million in salaries after this trade, leaving them $6 million below the first tax apron. By including Duop Reath's $2 million, this trade succeeds to give the Blazers an All-Star to lead the next generation without exceeding that threshold. Pairing Garland with standout forward Toumani Camara and talented guards like Shaedon Sharpe and Scoot Henderson could prepare Portland for a worthwhile future. around a great core.
For the Cavaliers, the fit and need for Jrue Holiday is evident. Cleveland's backcourt defense continues to struggle, and as their seasons are defined not by regular season wins but by postseason disappointments, a two-time champion like Holiday is a perfect addition. Though his acquisition would be costly by dealing Garland, the Cavs cannot ignore the impact Holiday could have to fit alongside Donovan Mitchell as a primary facilitator and defensive anchor.
The 34-year-old guard averaged 11.1 points and 3.9 assists with Boston last season and has been named to the NBA's All-Defensive teams each of the four seasons prior. This past season, Holiday missed the 65-game threshold by just three games, disqualifying him from his fifth consecutive honors.
The age gap between Garland and Holiday is noteworthy, but with reports that the Cavs jumped into the Kevin Durant fray and potentially offered Garland, Cleveland seems to be willing to trade youth for a win-now championship move. Perhaps even more than Durant, Holiday fits that bill for the Cavaliers as a game changer for the coming season.
With three postseasons giving the Cleveland Cavaliers' core a wealth of playoff experience, adding a veteran who knows not only how to survive the playoffs but win it all could quickly prove to be the final piece necessary to accomplish what this Cavs team is dreaming to do. It's time for another parade in downtown, and Holiday gives the city a great chance at that becoming reality.