In many ways, the season ended before it began. The Cleveland Cavaliers lost too much talent. The roster had an imbalance of veterans well past their prime, in addition to younger assets without much proven ability.

Through wise trades with long-term significance, the Cavaliers front office dealt their veterans for more than their worth. In return, Cleveland took on bad contracts from other teams, contracts that will expire after the 2019-2020 season.

For example, when the Cavaliers traded Alec Burks in a three-team trade with the Houston Rockets and Sacramento Kings, they received what the organization thought was a “coveted first-round pick,” from Houston. While the Cavaliers received the awful Brandon Knight contract from Houston ($14.6 million this season, $15.6 million in 2019-2020), they got just what they wanted.

The Cavaliers had little financial flexibility, regardless if Knight was on their payroll or not. Without taking any risk at all, the Cavaliers added his contract in order to take the Rockets first-round pick, conveyed this upcoming draft. Since Houston has been in win-now mode, the late first-round pick proved insignificant for them. It means everything for Cleveland, however.

The 2019 Draft

Given their financial constraints, the 2019-2020 Cavaliers will prove mediocre on the court, no matter who they select with their lottery pick in the 2019 NBA Draft. Even if the lottery balls favor Cleveland’s luck, it’s difficult to envision Duke University superstar Zion Williamson will turn the unfortunate Cavaliers into a playoff contender. LeBron James couldn’t even lead Cleveland to a playoff appearance in his first season. It’ll be no different, even if Cleveland gets the first pick.

While the league continues to utilize a lottery format for draft order, it’s increasingly unlikely Cleveland would get the first pick over the New York Knicks. I won’t admit the NBA lottery is fixed, but it’s challenging to envision a scenario where the NBA preferred Williamson get drafted by Cleveland over New York. In obvious circumstances, New York stands as the better sports city to market a blossoming superstar in Williamson.

Since the bottom three teams all have the same odds of the first pick (league rules changed), the Cavaliers will likely draft either second or third, in an ideal scenario. This leaves either Duke small-forward RJ Barrett or Murray State University guard Ja Morant as the only players worthy of a selection this high.

ESPN’s most recent mock draft had the Cavaliers selecting Barrett with the second pick and Iowa State University forward Taylor Horton-Tucker with the Rockets pick (currently valued at 21st overall).

If Cleveland can hit on these two draft picks, it could set their rebuild ahead of schedule, where in the 2020 offseason, the ability to sign free agents will be much easier for Cleveland.

While the organization spent $34 million to add eight draft picks during the last eight months, only one of these selections happens for the 2019 draft. The plethora of second-round picks won’t convey until 2020, at the earliest. It’s likely they package these to move up in future drafts.

The Cavaliers also acquired a 2021 first-round pick from the Milwaukee Bucks.

Contract Situations

Unfortunately, their financial situation next season will prevent Cleveland from avoiding a season similar to that of 2018-2019. Right now, Cleveland currently has 11 contracts on their payroll next season, one of which belongs to JR Smith. While he’s set to earn $15.6 million from the Cavaliers next season, it’s not fully guaranteed. Before the start of training camp, Cleveland will likely look to move Smith in exchange for an expiring contract of equal value.

Including Smith’s contract, the Cavaliers owe $134 million toward 11 players. Starting next season, all-star Kevin Love’s four-year/$120 million contract extension kicks in. On the surface, Love’s contract appears undesirable for a player of his injury history and skill decline. At the moment, however, he’s one of only four players under contract for the 2020-2021 season. The others include: Collin Sexton, Larry Nance Jr. and Ante Zizic. From the 2019-2020 season to the 2020-2021 season, the Cavaliers payroll decreases from $134 million to $51.8 million.

Tristan Thompson, Jordan Clarkson, John Henson, Matthew Dellavedova, Cedi Osman, Knight and Smith all have contracts which expire during the 2020 offseason. Other than Osman and Dellavedova, none of the other players should return to the Cavaliers. The organization will likely consider bringing Thompson, but given his contract status ($18.5 million), he’s not worth the investment, again.

While it might not seem like it now, the Cavaliers are in a prime position to add high-quality free agents during the 2020 offseason.

2019-2020 Season and Beyond

The organization will likely undergo a coaching staff overhaul during the offseason, but the roster won’t give them much to work with.

Since their financial flexibility isn’t positive next season, the organization will struggle to build a playoff contending roster with much needed depth. Aside from both first-round picks, the roster should look almost the same, which isn’t terrible, in terms of future applications.

If Cleveland can hit on both first-round picks this offseason, the franchise will be in an excellent position going forward. While the 2019-2020 Cleveland Cavaliers won’t compete for any meaningful playoff spot in the Eastern Conference, the future after next season looks bright.

The younger assets, like Osman, Sexton and Nance Jr., will continue to improve. If Love stays healthy, the team will already have their all-star and franchise cornerstone with which to build around.

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