Want to know a fun fact? After Dan Gilbert purchased the Cleveland Cavaliers in 2005, the organization has won six Central Division championships (2009, 2010, 2015, 2016, 2017, 2018), five Eastern Conference championships (2007, 2015, 2016, 2017, 2018) and one NBA championship (2016) which ended the 52-year Cleveland sports curse. Want to know an even more fun fact? The Cavaliers under Gilbert's tenure also have never made the playoffs, or come close to any of the above accomplishments, without LeBron James on the roster.
It's safe to assume that other than hiring a college coach to run the team, Gilbert's white whale is making the playoffs without James. Cleveland has already tried to catch the first whale, hiring former Michigan coach John Beilein to coach the team. Unfortunately, that failed in spectacular fashion with Beilein quitting mid-season and J.B. Bickerstaff, the correct hire all along, taking over as the team's head coach.
The second white whale, meanwhile, still might be in reach for the Cavaliers this offseason. Philadelphia 76ers superstar forward Ben Simmons has reportedly demanded a trade and is refusing to report to training camp in a few weeks to really drive his point home. According to sources, Simmons's preference is to go to either Los Angeles-based team or the Golden State Warriors. But, those same sources also said that Simmons would also be open to joining the Cavaliers as well.
"Ben is super close with Darius Garland through sharing the same agency in Klutch. That's one of the driving factors in his openness to going to Cleveland," said an Eastern Conference executive. "He also wants a fresh start with a team where he is clearly the best player and he would get that treatment there. More than anything, he just wants to be wanted and appreciated."
At first, it's tough to see how Cleveland can cobble together a package that entices Philadelphia. Sure, after LeBron James left town for a second time the Cavaliers have assembled a ton of impressive young pieces in a limited amount of time. But, the 76ers are a team that is wired to win now under superstar big man Joel Embiid. Why would Philadelphia want a bunch of young players that need time to further develop when a championship next season is the goal? That, and when you look at Simmons at face value, why would they want to trade him for anything?
At only 25 years old, Simmons is already a perennial Defensive Player of the Year candidate for his position and has the ability to defend anyone on the floor. Offensively, meanwhile, the 6-10 All-Star Australian forward is an incredibly gifted playmaker as well. Yes, there are shooting limitations and concerns outside of the paint and at the free throw line. There are also concerns about his meltdown last season in the playoffs against Atlanta. But, despite this, 76ers general manager Daryl Morey is asking for a premium due to Simmons's aforementioned skillset and abilities.
The issue for Morey and the rest of the Philadelphia organization is they have no choice. With Simmons's trade demands now public, it's only inevitable that in the coming days the 76ers will find a new home for him. That sunk Simmons's value across the league and the concerns after his early playoff exit have an impact as well. Again, Philadelphia has no practical use for the young assets Cleveland has assembled. But, there could be a trade out there involving multiple teams that lands the Cavaliers Simmons while the 76ers get key veterans to help them win a championship now.
Look at teams like the Memphis Grizzlies, who are looking to move key veterans Kyle Anderson and Dillon Brooks due to a cluttered young rotation. A trade that sends Simmons to Cleveland, Isaac Okoro and a future pick to Memphis while Philadelphia gets Kevin Love and Dillon Brooks makes some sense. If that doesn't work how about adding the Indiana Pacers to the mix instead? The Pacers would land Love and Collin Sexton, the Cavaliers get Simmons and the 76ers obtain Malcolm Brogdon and a 2022 first round pick from Cleveland.
The situation remains fluid and according to sources, the likely favorites to trade for Simmons are still the Minnesota Timberwolves or the Sacramento Kings. But, one Western Conference executive shared that he views the Cavaliers as a darkhorse option to obtain Simmons before the start of training camp. Sure, there are concerns with the overall fit between Simmons and the rest of this roster in terms of spacing. But, Cleveland cannot be too particular when it comes to acquiring any form of talent – especially one like Simmons.
There's a reason why the Cavaliers are consistently in the bottom of the Eastern Conference, they don't have a star to tie everything they've assembled together. Cleveland might have that in Evan Mobley one day but he's going to need time to grow and adjust to the NBA game. If Cleveland obtains the disgruntled superstar, who again is open to coming here, they could realistically make the playoffs next season. Simmons could be the star now that makes things make sense for the Cavaliers now and could be the reason they're a force in the Eastern Conference once the rest of the team catches up.