Bleacher Report suggests Cavaliers should sign a puzzling free agent

Although the NBA news cycle seems particularly quiet with the majority of news being training camp deals, there are still talented players looking to sign their next contract. After the first Cleveland Cavaliers signed Tristan Thompson, they still have some room to add another player if they want.

As it stands, the Cavs have their backcourt depth set primarily in Darius Garland, Donovan Mitchell, Caris LeVert, and Ty Jerome (Ricky Rubio, as well, upon his possible return). In the frontcourt, Tristan Thompson joins Jarrett Allen, Evan Mobley, Damian Jones, and some combination of minutes for Georges Niang and Dean Wade.

While the Cleveland depth is solidly filled in these areas, their forward depth is still their shallowest. They acquired sharpshooter Max Strus in a sign-and-trade and retained Isaac Okoro in the deal. Additionally, Dean Wade is likely to continue playing a chunk of time at the three spot when the Cavs need his height, considering the short stature of Strus and Okoro. They also still have a non-guaranteed contract for Sam Merrill and a two-way deal with Emoni Bates, but there is no confirmation on their plans with these players this season.

Thus, any final addition in Cleveland will likely bolster their wing depth, especially in outside shooting. Earlier in the summer, the Cavs were rumored to show interest in a second sign-and-trade for P.J. Washington, although it never materialized. Adding another player to their ranks could still work, either from the remaining free agents or in a trade.

In a recent article, Bleacher Report’s Andy Bailey discussed the best landing spot for the NBA’s 10 best remaining free agents, naming the Cavaliers in the article. Bailey considered the player’s skillset and the remaining needs of each team from his perspective.

With names like Kelly Oubre Jr. surprisingly still on the market, free agency is anything but empty. With superstar trades possibly on the horizon, many of the names on the list reasonably are best suited to sign with one of the contenders in the midst of trade rumors as roster spots and minutes become available.

Following Ricky Rubio’s decision to step away from basketball for the time being to focus on his mental health and his family, Bleacher Report suggested the Cavaliers find a replacement for Rubio in a former top 10 pick in Justise Winslow.

Winslow was selected 10th overall in 2015 by the Miami Heat, where he played his first five NBA seasons. Eventually, Winslow left for Memphis and then the Clippers a year later. Since a trade in 2021, Winslow has played for the Portland Trail Blazers bench, averaging 26.8 minutes per game. Winslow entered free agency after a string of injuries led to a necessary ankle procedure, ending his season.

In his 29 games played last season, Winslow started in 11 and averaged 6.8 points, 5 rebounds, and 3.4 assists. Where Andy Bailey found intrigue in Winslow’s game was his unique talent as a wing with playmaking potential. Although Winslow began his career with only 1.5 assists per contest in his rookie season, he has continually improved as a passer.

Bailey suggested Winslow could be a possible Ricky Rubio improvement this season and provide another perimeter defensive tool for the Cavs. Signing another playmaker would certainly improve Cleveland’s overall versatility, but Winslow’s offense dissipates outside of his passing talent. In his last three seasons, Winslow has averaged 6.3 points on a poor 42.8 efficient field goal percentage. On top of that, his 3-point shot has never come around, shooting 23.6 percent from deep in that timeframe.

The Cavs would not expect any heavy scoring responsibilities for Winslow, though, and 3-point shooting is not the only important statistic. But, his inefficient overall scoring paired with his ineffective shooting would only serve to negate much of the 3-point improvements the Cavaliers made this summer. With two non-shooters in the starting lineup with Mobley and Allen, prioritizing long range capabilities to surround them is not even a question but a necessity.

Bailey’s assessment of Winslow as a valuable last minute signing in the NBA is not wrong, as he can produce on defense with an alright offensive game to match. In Cleveland, however, it is hard to imagine a positive situation for Winslow to show his skillset or improve his game.

With T.J. Warren and other veteran wing shooters still available, the Cavaliers will likely be better suited working out a deal with one of them or making a last minute trade before training camp.

The offseason is not yet finished, and the Cavs may find one final player before training camp, or they could stand pat and focus on developing their in-house talent.