Brad Stevens spent eight years as Celtics head coach prior to moving upstairs to his current role as President of Basketball Operations prior to the 2021-22 season. Considering his time in college, he has spent twenty years as a coach (14 seasons as a head coach) during his career and less than a year and a half as an executive. It only stands for reason that Stevens’ long-standing experience as a head coach would have a significant impact on how he approaches roster construction.

Indeed, Stevens has decisively reshaped the Celtics roster since taking over. While his predecessor, Danny Ainge, built an excellent talent foundation primarily through the draft (see: Tatum, Brown, Smart, Rob, Grant, Pritchard), Stevens has accentuated that preexisting talent base with savvy, veteran acquisitions and overseen a roster that has the most wins in the NBA (including playoffs) since the beginning of his front office tenure.

How does Stevens’ coaching background inform his decision-making in the front office? How does his approach differ from Ainge’s (in)famously stinginess? How might Stevens’ philosophy impact his handling of the upcoming NBA trade deadline as he seeks to push a contending roster over the top?

The goal here is not to debate which executive is better. On balance, I would consider Ainge’s run as the Celtics’ lead decision-maker over almost two decades to rank in the top quarter of the league if not higher. Similarly, Stevens has done an excellent job since taking over. Instead, let’s explore a few key factors that differentiate Stevens from Ainge.

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1. Motivations when making significant trades: Ainge was known for constantly trying to “win” trades in terms of value extracted or assets acquired. Stevens’ three major deals so far (Horford, White, and Brogdon) have seen the Celtics give up a fair amount of assets in the form of young players and first round picks. Stevens’ motivation when making major deals has been to identify and acquire veterans on long term deals that complement his existing core. Sheer talent and acquisition cost appear secondary to on-and-off court fit.
2. Prioritization of team chemistry and role definition: A coach constantly thinks in terms of rotations, minutes, and roles. In the NBA, regular season rotations generally include 9-10 players while playoff rotations can often tighten up to a top-7 or -8. A locker room is a fragile ecosystem, and the easiest way to destroy that ecosystem is to have players on the roster who do not accept, or ideally embrace, their roles. Many GMs have a background in scouting or talent evaluation and operate more as talent collectors. Fans, similarly, often view roster construction primarily as a talent acquisition exercise where they can move players around like pieces on a chessboard via trade machines or 2k franchise.

Stevens’ coaching background, however, makes him exceedingly sensitive to how moves impact role definition and chemistry throughout the whole roster. For instance, while most clamored for Stevens to fill out the back end of the roster last summer with more established veteran minimum options (or even by using the large $17.1M Fournier TPE before it expired), Stevens likely viewed his team’s regular season and playoffs As already intact after the Brogdon trade. Consequently, he probably concluded that adding further players that might expect a regular rotation role would provide a diminishing return on investment.

3. Willingness to trade draft picks for veterans: Ainge frequently held on to future draft picks and assets rather than cashing them in for veteran trades. He valued flexibility to pursue future big swings. Stevens has not hesitated to include assets for veterans. Cumulatively, he has sent out three first round picks, one pick swap, and young players like Romeo Langford and Aaron Nesmith to acquire Horford, White, and Brogdon. Any coach will tell you that veteran teams are typically more ready to win than teams that skew young. Stevens, in both trades and extensions for Smart and Rob, has mostly targeted veterans that are still in their prime.

The Upcoming NBA Trade Deadline

So how will Stevens’ coaching-centric decision-making process impact his approach to the upcoming NBA trade deadline? First off, I would not expect major fireworks this deadline. The Celtics have a clear top-8 playoff rotation: Smart, Brown, Tatum, Horford, Rob, Brogdon, White, Grant. If they are all healthy, those eight players will likely play every single high-leverage playoff minute. The Celtics advanced to Game 6 of the NBA Finals with, essentially, a 7-man rotation last year (they did not play much once Rob returned and Pritchard’s role was inconsistent). Adding Brogdon to the mix means that the playoff rotation is airtight and even deeper than last year.

Additionally, Stevens’ gamble with the back end of the roster seems to have paid off to this point in the regular season as they hold the best record in the league. While they are all flawed players that are probably not ready for the crucible playoff, Kornet, Hauser, Pritchard, and Griffin have all been useful at times. They seem capable of effectively filling those 9-12 regular season fringe rotation spots. Therefore, it is unlikely that Stevens can find an acquisition that is both attainable and an upgrade on his current rotation. Even though I predict a quiet deadline for the Celtics, trades are fun, so let’s briefly explore a few ideas that might work with Stevens’ philosophy of adding veterans that fit a role but do not threaten team chemistry and role definition.

The Sacrifice Bunt

Suns Receive: Justin Jackson ($1.8M) and a 2023 2nd Rd Pick

Celtics Receive: Torrey Craig ($5.1M)

Breakdown: The Celtics would absorb Craig into their $5.9M TPE while the Suns, who are sinking fast, save some luxury tax money and add a 2nd for a non-core player. Craig would bolster wing depth (arguably the thinnest position on the team) down the stretch of the regular season allowing Tatum and Brown to sneak some extra rest here and there. The Celtics wouldn’t improve their 8-man playoff rotation with this move, but they also wouldn’t give up much.

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Stevens Hits a Single – The This-Style Deal Part Two

Jazz Receive: Payton Pritchard, Danilo Gallinari, and Justin Jackson (combined $10.8M)

Celtics Receive: Kelly Olynyk ($12.8M)

Breakdown: The Jazz will likely be active at the trade deadline, and this move reunites Ainge with his former draft pick, Pritchard, who has upside as a strong shooting backup point guard in the league. If the Jazz move on from guards like Mike Conley or even Jordan Clarkson, Pritchard could be a nice project for them.

Meanwhile, Olynyk would become this year’s Daniel Theis in terms of a trade deadline pickup who is also a former Celtic that Stevens is comfortable with. While he would likely not crack a Celtics 8-man playoff rotation with everyone healthy, he would become quality insurance in case any one of Rob Williams, Al Horford, or Grant Williams had to miss time during the playoffs or end of the regular season. Olynyk’s ability to play the 4 or the 5 and shoot from the outside allows him to fit in fairly seamlessly with any of the Celtics current bigs. Olynyk’s $12M salary for next year is expensive for an insurance option, but only $3M of it is guaranteed.

The unique nature of his deal next year would give the Celtics more peace of mind as they plan around Rob’s health concerns and the pending restricted free agency negotiations with Grant. Assuming Grant gets re-signed and Rob finishes the season healthy, Olynyk’s full contract for next year may or may not be picked up. But, if the Celtics do pick it up, it could still be useful for any deals the Celtics might make during the 2023 offseason or the 2024 trade deadline (just as Theis contract was fundamental to matching salary in the Brogdon deal).

The Big Swing – Homer or Strikeout?

Hawks Receive: Derrick White and Grant Williams (combined $21.1M)

Celtics Receive: John Collins ($23.5M)

Breakdown: Full disclosure – I would not do this deal, but it is an intriguing thought exercise. Collins has been heavily involved in trade rumors for a while now, and he seems to be one of the most likely players to be dealt at the deadline. The Hawks could certainly use a roster shakeup. White and Grant would be great fits on the Hawks for the same reasons they are great fits on the Celtics. They are unselfish role players who can hit open shots, play great defense, and don’t dominate the ball. The Hawks need more players like that.

If the Celtics were to entertain a deal of this nature, they would obviously have to hold a strong belief in Collins’ fit as the long-term starting 4 next to Smart, Brown, Tatum, and Rob. Essentially, Collins would become the Horford replacement the Celtics would need eventually. While I think it would be too much risk to take on to shake up an 8-man rotation that has been as effective as the one Stevens has assembled for this year, Collins does fit Stevens’ modus operandi in one area. He is a young veteran who, in his prime, signed to a long-term contract. Collins has three years and $78 million left on his deal after this season (his final year is a player option). Although that contract may sound cost-prohibitive, keep in mind that White makes about $17M per year, and Grant’s new contract this summer will likely land in the mid-teens as well. Starting next year, Collins will actually be cheaper than White and Grant combined.