The long, painful season for the Cleveland Cavaliers has officially come to an end with many questions about the future of the franchise needing answered.

After another rebuilding season which resulted in a 22-50 record, the third-worst in the Eastern Conference and tied for fourth-worst in the NBA, many wonder if the Cavaliers will ever get out of the cellar and become a competent NBA franchise once again.

It’s completely fair to question the vision and plan for the Cavaliers as they’re trying to push forward in the post-Lebron James era but with another season of not much growth an offseason with some franchise-altering decisions lying ahead, what the Cavaliers do could either push them closer towards a return to the postseason or leave them stuck in a very bad position for the next several seasons.

The Lottery

Cleveland is tied with Oklahoma City for the fourth-best odds in the NBA Draft Lottery currently with a coin flip next week deciding who will have the better odds come June 22. If Cleveland wins the coin flip, they’ll have a 12.5% chance of landing the #1 pick but if they lose, they’ll gave a 10.5% chance.

This draft is projected to have four elite prospects in Oklahoma State’s Cade Cunningham, USC’s Evan Mobley, Gonzaga’s Jalen Suggs, and the G-League’s Jalen Green.

The Cavaliers haven’t had the best lottery luck the last couple years the new format dropping down to fifth in each of the last two drafts although they’ve landed some talented pieces in Darius Garland and Issac Okoro. It’s important the luck returns to Cleveland because one of the top four prospects could set the franchise in the right direction but if they don’t and while they could land a solid prospect such as Jonathan Kuminga or Scottie Barnes, it won’t change the fortune of the franchise the way Cunningham, Mobley, Suggs, or Green can.

Contract Extensions

The Cavaliers have two big decisions to make this offseason as it may have to load out some big contracts to two players of their future.

Jarrett Allen is scheduled to become a restricted free agent while Collin Sexton is eligible for a rookie-extension with both potentially receiving over $100 million dollars in new contracts.

Cleveland picked up Allen as part of the trade that sent James Harden to the Brooklyn Nets with the Cavaliers only giving up Dante Exum and a future first-round pick they owned from the Milwaukee Bucks.

Allen was an impact player for Cleveland averaging 13.2 points, 9.9 rebounds, and 1.4 blocks per game although down the stretch I think the losing really started to wear on Allen as his numbers slipped through April and May. The rumored contract numbers have Allen likely getting between $20-25 million per year on average and while Cleveland didn’t want to give that to Andre Drummond, it’s likely they will give that to Allen despite not fitting the mold of what NBA teams would like in a center in today’s style of play.

Sexton has been a solid player for Cleveland since they drafted him eighth overall in the 2018 NBA Draft and has improved in each season of his young career. This season he posted career highs with 24.3 points, 4.4 assists and shooting 47.5% from the field.

Now the problem is going to be surrounding Sexton is what himself and his representatives are going to want in a contract extension and what Cleveland is going to be willing to give him. The Cavaliers can offer him a five-year extension worth $167.9 million or a four-year extension worth $129.7 million. I like Sexton’s game but he’s definitely not a max-level player and I don’t know if the Cavaliers truly feel he’s a max-level player especially considering it’s been reported some in the organization think he’s best suited in a sixth-man type role going forward.

Cleveland doesn’t have to offer him an extension this offseason and they very well could wait which may be the smartest thing to do. Let Sexton bet on himself and see how hard he works and there’s no doubting the man’s work ethic but if the Cavaliers don’t feel ready to “throw the bag” at the upcoming fourth-year guard, then let him go out in the 2021-22 campaign and prove he’s worth it.

The Kevin Love situation

This may be the biggest task for the Cavaliers this offseason, what to do with Kevin Love moving forward.

The former All-Star forward isn’t the same player he used to be and the relationship between Love and the organization definitely isn’t as strong as it was during the team’s Finals run alongside Lebron James and Kyrie Irving.

I think both sides can honestly say it was a mistake to agree to a four-year, $120 million extension following James’ exit after the 2018 NBA Finals which it more than likely was pushed by owner Dan Gilbert and his attempt to save face after James departed the organization for the second time.

Love has been constantly injured and when he has been on the court, he hasn’t displayed the leadership you would expect out of a 12-year NBA veteran. Yes, the losing and turmoil hasn’t been fun but Love signed up for this when he signed the contract extension and he knew what he was getting into. Acting immature and throwing temper tantrums on the court isn’t good behavior.

There’s two years and $60 million remaining on Love’s contract and it’s not likely any teams will want to acquire that in a trade this offseason despite Love’s recent comments about wanting to join his home state Portland Trail Blazers.

More than likely the two sides will have to come to an agreement on a buyout or Cleveland uses the stretch waive on his contract and eats the remaining $60 million over a five-year period with a $12 million dead cap from 2021-22 through 2025-26.

I don’t know if this is in the Cavaliers’ plans but it’s been more apparent than ever that the relationship between Kevin Love and the Cleveland Cavaliers needs to come to an end this offseason. Myself and many Cavs fans will be forever grateful for Love’s contribution towards the 2016 NBA Championship but the dark cloud his on-court behavior and his contract that hang over the organization needs to go.

Will Changes be Made at the Top?

It’s fair for fans to wonder if Dan Gilbert will make any changes to the organization as the team sits in the position they’re in after three seasons into the rebuild.

The rumors have been out there since around the All-Star Break that general manager Koby Altman could be on the hot seat despite signing a contract extension about 18 months ago.

Altman has made some solid decisions as general manager with the drafting of Sexton, Garland, and Okoro along with signing Larry Nance to a team-friendly extension as well as the trade for Jarrett Allen.

There is also the questionable decisions like not getting anything for Andre Drummond at the trade deadline, the Kevin Porter trade despite Porter’s off the court behavior/decision making, the hiring of John Beilein, and the Love contract extension although the latter two should be more on Gilbert than Altman.

I don’t think Altman should be replaced but I also think this offseason and next season should likely be the make or break year. However, if they do decide on replacing him, this won’t be a good look once again for Dan Gilbert.

Gilbert has proven time and time again that despite his commitment to spending a very high payroll during the Lebron James era that he is not a good NBA owner and is not a good at decision making when it comes to hiring general managers and head coaches since becoming the owner of the Cavaliers in 2005.

Since buying the team from Gordon Gund, Gilbert’s win percentage in the seven seasons without Lebron James is .296 and in that span, Gilbert has had six different head coaches and three general managers.

So if they do fire Altman and look to replace him, Gilbert will likely try to lure Brock Aller, the New York Knicks’ current VP of Basketball and Strategic Planning and formerly the Cavaliers’ senior director of basketball operations because Gilbert doesn’t do thorough searches for executives and usually hires from within or people he “trusts” which you can translate to “someone who will say yes to whatever Dan Gilbert wants”.

If they do fire Altman, that likely won’t spell good news for head coach JB Bickerstaff because Gilbert wanted Beilein when the team went on a search for a head coach two years ago when Altman wanted Bickerstaff and made him the associate head coach and subsequently the head coach after Beilein re-signed halfway through the 2019-20 season.

Should the Cavaliers make significant changes in the organization this offseason, hopefully fans will wake up and realize that the team will never get back to the winning ways as long as Dan Gilbert is running the show.

I know he’s had a tough time the last few years because of his health but as Jay Crawford said in a recent interview on the Locked on Cavs podcast, Gilbert runs the Cavaliers the way Jerry Jones runs the Cowboys and neither one will likely taste success the way they have before because they can’t let their egos stay out of the way.