Dealing with future early adopters extends to the title window

There is more than one way to skin a cat.

While the frequent complaint about the NBA product on the field is uniform playing styles, roster building in the league is anything but. Front offices and executives try several different ways to build their ideal team. From positional differences to skill overlap, and free agency to draft, there is real pleasure to be found in seeing a front office not only acquiring super talent, but discovering exactly how to maximize the group around them.

Over the past five years, the difficult part of the equation has been completed for Boston Celtics. They got their stars, and they did so through the draft. Jaylen Brown and Jason Tatum, who were picked in back-to-back drafts, became All-Stars and cemented their positions at the top of the standings in Boston by leading the Celtics to the 2022 championship. The NBA Finals. Brown is only 25 years old, and Tatum is 24. If the history of the other stars is any indication, they will both be in their prime for the better part of the next decade.

Photo by Garrett Ellwood/NBAE via Getty Images

Outside of acquiring talent and keeping them happy, the front offices have to do some tidy gymnastics, get around and evade the luxury tax and play within CBA rules to build a competitive team around these stars. Tatum and Brown, both of whom are maximum deals signed at the moment, will unite to bring in $59 million next year, According to Spotrac. That number will jump to $63.3 million next year, last year Jaylen was under contract before he could negotiate a significant increase in his deal. In order to keep these two together, the Celtics will either need to spend well on the luxury tax or find ways to highlight cheap contracts on menu margins.

Fourteen months ago, Brad Stevens snuck into the main front office chair, and took over Danny Aing as head of basketball operations. Stevens’ first step was to pick the 2021 first round with Kemba Walker to acquire Al Horford. This was seen by many as a cap-driven move at the time, trading off Walker’s excess amount for a better deal and forgoing the first late move as a cost of doing business. Horford ended up being a major possession on the field and a perfect player on the roster.

At the 2022 trading deadline, Stevens was at it again, taking the first player in 2022 to San Antonio (along with Romeo Langford and Josh Richardson) for Derek White. White, an underrated role player stuck in a backcourt in San Antonio, was another veteran piece who could provide some backcourt depth to the Celtics, who never found the right replacement for Kemba. White proved it all for the Celtics, making a big splash in the post-season and merging perfectly with their already well-established core.

The third installment of the “Stevens trades a pick” saga has been revealed with the acquisition of Malcolm Brogdon. On the face of it, Brogdon is the best player Stevens has had in his time as Celtics’ general manager, and it only took one piece of venture capital (the 2023 first round pick) to pull him off. Also included in the deal with Indiana was salary fillers (most notably Daniel Theiss and Aaron Nesmith).

Nearly fourteen months in the job, Stevens has apparently been stalking on the draft during his first three years on the job. Some headers may be concerned about the eventual shortage of cheap contracts with the team in control. Grant Williams is due to sign a new contract next summer. Once that happens, Payton Pritchard will be the only first-round pick by the Celtics still on the roster.

But that isn’t necessarily a bad thing. Stevens has already shown, through deals with Horford, White and Brugdon, what his way forward is to build the roster.

Boston Celtics press conference for Gallinari and Brugdon

Photo by Jonathan Wiggs/The Boston Globe via Getty Images

The first step is to keep the flexibility at the back of the list. Throughout the regular season, this flexibility will allow the Celtics to be able to add the appropriate bench end pieces based on who is available and what their team needs. Players who add them can be veterans (like Nik Stauskas) or junior players from the G-League good enough to be on the roster (like Malik Fitts). C can easily swallow one of their contracts if the right veteran is available in the buyout market without jeopardizing the long-term plan.

Stevens’ key is to sign each player for an additional year of unsecured salary. This mechanism allows the Celtics to group these pieces together for a summer trade (as they did with Fitts, Juwan Morgan, and Stauskas) to gain a better role.

Giving them an extra year at the back end of the contract gives them team control in a new year, but is designed to circumvent Stepien’s rules that dictate trading draft picks. Under the Stepien rule, an NBA team cannot trade first-round draft picks in the future in consecutive years. When the league year ends in July, though, that clock is reset.

This year is an example of how that works. On the deadline, since the Celtics swapped their 2022 first-round pick with White, they won’t be able to handle the 2023 selection until after July 1, 2022. Once the league’s new year begins, a contract for such a deal is back on the table. We could see the same next year: Boston doesn’t have a 2023 option, so they can’t handle picking 2024 in any mid-season trade. Next July, that limitation disappears.

Stevens will probably fill the rest of the list this summer with some G-League standouts, minimal veterans and interesting young players. Look for them all to be given a two-year deal with the second year completely unsecured, only for purposes of use in a deal later.

With the cost of the roster rising in the coming years due to the impending free agency of Grant Williams and Al Horford, as well as mounting salaries for their contract players, the allure of retaining friendly salaries for the team matters. But choosing the first round is only one way to get a cheap contract.

With the Celtics still doing well (or at least planning to do well in the Tatum and Brown years), the value of a first-round pick isn’t that great. Most of the choices for them will be in their twenties, and it is very difficult to find impactful beginners early in their career in those locations. We’ve already seen the dangers of trying to develop talent while chasing a championship; Nesmith and Langford were victims of a lack of a longer leash to play through fouls and a lack of refinement to play without making them.

Furthermore, future first-round picks can be leveraged to help eliminate the contract. With C players stacking up so expensive, the luxury tax repeater penalty can breathe into the property neck to trim one or more of the role player’s costly contracts. The first round of sweeteners is great in deals for any team that takes money out of their hands, and can help create trade exceptions for Celtics if traded to the right team with the cover space.

The point here is: While the cost of the list increases, don’t assume that the remedy for this expense is to control our choices in the first round. Yes, first-round picks are cheap and have value as a result. But the Celtics could find better uses for them to help players acquire roles, offset expensive contracts, and keep the title window open in the long run. If you’re a betting guy, I think it will take some time before the Celtics pick the first round again.