There is a sense of optimism in Cleveland. The Cavaliers finally have stability at head coach with JB Bickerstaff, a likely top-five pick in the draft, a young core and an All-Star in Andre Drummond. Most importantly, Kevin Love is healthy.
Now heading into the offseason, let's look ahead to the draft, free-agency and trade decisions that Cleveland will face.
Note: The financials in here are based on the salary cap and luxury tax holding at the 2019-20 levels, as expected.
MORE: Biggest trade, free agency and draft decisions for every eliminated NBA team
The direction in the draft
The Cavaliers have built their roster organically through the draft in the post-LeBron James era, taking a big-picture approach. Their lottery pick this October will become the fifth out of the 11 players on the roster selected in the first round since 2018.
Two lottery picks, Collin Sexton and Darius Garland, play a position that is top-heavy in this year's draft. In the latest ESPN top 100, guards LaMelo Ball and Anthony Edwards rank in the top three.
Leading up to the draft, the Cavaliers will need to ask the below questions:
In a point guard-heavy draft, do we go best available or by positional fit?
The Sexton-Garland backcourt is the smallest in the NBA, both measuring in at 6-foot-1. In the 1,255 minutes when both were on the court, Cleveland had a defensive rating of 117.3 -- the worst among lineups that played more than 500 minutes.
Sexton played 100% of his possessions at point guard in his rookie season, but has played 77% of his possessions at shooting guard this year, per Basketball Reference.
Do we select a center like James Wiseman, a less expensive option to Andre Drummond and an insurance policy if we lose Tristan Thompson?
Drummond is likely to opt into his $28.8 million player option and will enter 2020-21 on an expiring contract. Thompson is an unrestricted free agent.
Is there value in moving back in the draft to acquire draft picks and veteran players who can help now?
The cost at center: Andre Drummond and Tristan Thompson
The Cavaliers took a flier on Drummond at the trade deadline, acquiring the All-Star for a future second-round pick from the Detroit Pistons. The trade was a two-month audition for Drummond, who has a $28.8 million player option for 2020-21, and for the Cavaliers to see if he is a long-term fit. It also protected the Cavaliers in case Tristan Thompson leaves in free agency.
With Drummond likely to opt into his $28.8 million contract, can the Cavaliers afford tying up a minimum $43 million at the center position?
There is an overload at power forward with Kevin Love and Larry Nance Jr. and there is no proof that Drummond and Thompson can play together. Drummond and Thompson played a total of 11 minutes together in five games this season.
Because Thompson was not bought out of his contract prior to March 1, Cleveland can go the sign-and-trade route and look to extract value back. Thompson earned $18.5 million this season and would be subjected to base-year restrictions. The acquiring team, however, would be hard-capped.
The future of Kevin Love
Love averaged 32 minutes, 17.6 points and 9.8 rebounds per game while shooting 37.4% from 3 in 56 games in 2019-20, his most games since 2016-17.
Could the Cavaliers find a team willing to trade for Love with $31.3, $31.3 and $28.9 million left on his contract? If there are no trade packages of their liking, are they better off just keeping Love and the $90 million left on his deal instead of taking back expiring contracts?
The Cavaliers have never been a free-agent destination (unless your name is LeBron James) and going in the salary-dump direction without any value in return does nothing for Cleveland, but is Love willing to go through another year of rebuilding?
Offseason cap breakdown
Drummond's decision determines if the Cavaliers have cap flexibility in the offseason. If the center opts into his $28.8 million contract, Cleveland will be right at the $109.1 million salary cap. In the unlikely scenario that Drummond becomes a free agent and does not return, Cleveland would have $22 million in room.
The cap space takes into account Tristan Thompson's free-agent hold being renounced. Expect the Cavaliers to operate as a team over the cap and have the $9.3 million midlevel and $3.6 million biannual exception available.
The resources available to build the roster
The draft: No. 5 pick
The young players: Collin Sexton, Darius Garland, Dylan Windlier and Kevin Porter Jr.
Free agents: Andre Drummond (if he opts out) and Tristan Thompson
Potential cap flexibility (if Drummond opts out)
The Kevin Love contract
$9.3 million midlevel and $3.6 million biannual exception
$5.6 million to send out or receive in a trade
Dates to watch
Drummond has until Oct. 17 to opt into his contract for next season. He said that he "definitely" will be in Cleveland next season on a late June episode of the ESPN podcast Le Batard & Friends - STUpodity.
"Yeah, it's going to be hard to give up, so you can count on me being in Cleveland still," Drummond said. "I definitely will be in Cleveland."
Restrictions
Because their contracts are non-guaranteed, Alfonzo McKinnie's ($1.7 million), Jordan Bell's ($1.7 million) and Dean Wade's ($1.7 million) salaries do not count when it comes to a trade.
Extension candidates
If Andre Drummond opts in, Cleveland can begin negotiating an extension on Oct. 18 that can include an additional four seasons.The extension can be for 120% of his $28.8 million salary and has no limit on how much it can decline in Year 1. The Cavaliers will have until June 30, 2021, (subject to change) to negotiate a new deal.
The Cavaliers will still have cap flexibility in 2021-22 even if Drummond is extended. In addition to Drummond, Dante Exum is also extension-eligible.
The draft assets
The Cavaliers own all of their future first-round picks.
Here's how ESPN's Jonathan Givony and Mike Schmitz have Cleveland selecting in June:
• No. 5 (own): Deni Avdija | SG/SF | Macabbi Tel Aviv
Cleveland will receive Milwaukee's 2022 top-10 protected first-round pick. The pick is a protected top-10 in 2023 and top-eight in 2024. If not conveyed, Cleveland will receive 2024 and 2025 second-round picks from Milwaukee.