Analysis: Cedi Osman extends with the Cleveland Cavaliers

The Rookie Scale Extension deadline is in the past, but that doesn’t mean the NBA is done with extensions altogether. The 2017 CBA relaxed some of the restrictions on extending veteran contracts and we’ve seen a number of those extensions signed in recent seasons as a result. Veteran extensions have more flexibility with timing as well, as they can be extended at any point up until the day before a player becomes a free agent. On Thursday, news came down of the latest one: Cedi Osman will re-up with the Cleveland Cavaliers for another four years and nearly $31 million, per the New York Times’ Marc Stein.

Osman’s deal will feature declining salaries, according to Cleveland.com’s Chris Fedor, which means he’s set to make $8.75 million in 2020-21, $8.05 million in 2021-22, $7.35 million in 2022-23, and $6.65 million in 2023-24. Furthermore, the final year of the extension is non-guaranteed, giving the team an option to open up some additional flexibility in 2023-24 if they don’t want to keep Osman on their books.

Osman’s extension continues a recent trend of teams building in declining salaries into contracts and extensions. Declining salaries make any contract more palatable in a trade in the later years. There’s also the most uncertainty with respect to the player’s skill level in those years. In the short-term future, teams can be relatively certain of where they are in the league’s pecking order and how the player fits into their team, but years down the road, that becomes a lot more difficult. Osman’s deal reflects this, as the Cavaliers will pay him more money up front in the early years than they do in later on. Cleveland has done more of this in recent years: they structured Larry Nance’s extension to decline over the years. Kevin Love’s veteran extension rises in Year 2, then stays flat and drops back down in Years 3 and 4, as well.

The extension cuts out about $3.3 million in cap space for the Cavaliers next summer, as his free agent cap hold would have been about $5.52 million if he hadn’t signed an extension. However, they still project to have more than enough cap space to fill out their rebuilding roster and the 2020 free agent class is so low on talent that there’s no need to hoard cap space for the summer.

The lacking 2020 free agent class played to Osman’s favor, which is what makes this extension a little difficult to understand from his perspective. After Buddy Hield and Jaylen Brown both extended with their current teams ahead of the season, Osman’s place in the restricted free agent pecking order rose, to the point that he could have played his way into being one of the better free agents available this summer. In general, teams have seen this 2020 class coming and have pre-spent a lot of their 2020 cap space, as Cleveland has done in a small way here, but given that Osman is likely more of a bench player on a good team, his market is much wider than just the teams that will walk into July with cap space. Any team with their mid-level exception, which is projected to land at $9.84 million for next season, would also be open to Osman, giving him a lot more available suitors to bid against one another for him.

In a lot of extensions for younger players like Osman, teams are willing to pay them above the market rate to build in their growth as players over the life of the contract. This extension isn’t that – if Osman is never better than he is right now, then this contract will be just about fair for his services as a rotation player off the bench for a good team. He’s starting for this year’s team in Cleveland, but that’s not a good indication of where he would stand in the rotation on a team with a real chance at winning games.

He was elevated into a key role last year, playing starter’s minutes for the Cavaliers and acquitting himself well as a secondary playmaker on the wing. The addition of Darius Garland and the return of Kevin Love will take opportunities away from Osman this season, but with less shot creation responsibilities, perhaps he can get back to the more efficient level he demonstrated in his rookie year with the Cavaliers. Defensively, Osman is likely always going to be a negative, but he also plays a relatively low-impact defensive position on the wing; he won’t be a team’s point-of-attack defender and isn’t slated with defending the rim in any real way, so a smart team can mitigate his defensive weaknesses in the right scheme.

Osman’s jack-of-all-trades offensive skillset would have made him a very interesting addition to a number of teams this offseason. Pretty much every team in the league is looking for 6’8 guys with Osman’s skills as a playmaker and shooter; even if his three-point percentage dipped slightly last season, defenses respect his ability to hit that shot and will guard him out there, which is all you really need on the wing. He can get to the rim in spot-up situations if the catch-and-shoot jumper isn’t available and is fine with the ball in his hands as a secondary playmaker, though his decision making leaves something to be desired at times.

Unlike a lot of the young guys who were extended this offseason, Osman’s only just finished his second season in the NBA and his first as a real playmaking option after spending his rookie year on the 2017-18 LeBron-led Cavaliers. The technical ability is there for him to be a secondary playmaker off the bench on a good team and his ability to read the game and make good decisions will come with time and experience. He’ll have plenty of opportunities to hone his craft over the next few years on the rebuilding Cavaliers.

An extension at such a low value with declining salaries and a non-guaranteed fourth season is an A-plus move for a Cleveland front office that is slowly turning things around in the post-LeBron James era. Osman’s by no means a flashy player around whom a front office can build a team, but he’s a solid contributor and the club can scale his role up or down depending on how much they need from him. On a contract that’s guaranteed just $24.15 million for three years and comes in well below the mid-level exception for those seasons, the Cavaliers hit a home run on extending Osman.