Eastern Conference: NBA’s biggest what-ifs of the past five years

Few things inspire more debate than thinking back on what could have been.

That is particularly true when it comes to the NBA, a league chock-full of huge personalities and talents whose movements and moments have shaped its landscape. (Think “The Decision”, when LeBron James famously announced on live TV he was taking his talents to the Miami Heat.)

Recognizing that, and with (most of) the offseason officially behind us, we thought it would be fun to sit back and take a look at the biggest what-if scenarios for all 30 NBA teams over the past five years, dating back to the 2018 offseason.

What if Kevin Durant stayed healthy during his time with the Brooklyn Nets? What if Jimmy Butler remained with the Philadelphia 76ers and built a prolific dynamic duo with MVP Joel Embiid?

We’ll kick things off with a look at each of the 15 Eastern Conference teams’ biggest what-if, before shifting to the West on Wednesday.

What if the Atlanta Hawks didn’t make the conference finals in 2021?

The Hawks reaching the 2021 Eastern Conference finals was seen as Trae Young’s ascension to stardom. Instead, it was a team that caught a favorable draw and fortunate breaks; as a result, it achieved too much success too soon, and it has paid the price for it since.

By losing to Philadelphia in the second round, Atlanta’s season is seen for what it should have been: a solid success but one without the expectations that otherwise followed the Hawks into the 2021-22 season. As a result, the Hawks don’t have the same turmoil shadowing them through that campaign nor do they trade for Dejounte Murray last summer or fire Nate McMillan and Travis Schlenk this past season.

Instead, both are let go after the Hawks lose in the first round for a second straight season. And after Landry Fields ascended to take over the front office — but with Quin Snyder having gone to the Philadelphia 76ers after the season, rather than joining Atlanta during it — he would tap into his San Antonio connections and hire Ime Udoka as the team’s coach.

What if the Boston Celtics had re-signed Al Horford?

The summer of 2019 was a tumultuous one in Boston, as both Kyrie Irving (Brooklyn) and Horford (Philadelphia) departed on big-money free agent deals to other locales, and the Celtics responded by inking Kemba Walker to a four-year max contract through a sign-and-trade deal that sent Terry Rozier to the Charlotte Hornets. But after a hot start to his time in Boston, Walker’s knee quickly gave out on him, and he wound up being sent out in a deal — along with a first-round pick — to bring back Horford two years later.

With Horford on the roster in the NBA bubble for Boston in 2020, the Celtics don’t get dominated inside by Miami’s Bam Adebayo in the conference finals, and they make it to the NBA Finals. In addition, having Horford on the roster means Boston doesn’t need to sign Enes Kanter (now Enes Freedom). In turn, that means the Celtics keep the 30th pick in the 2020 draft, rather than trading it to the Memphis Grizzlies as part of a Kanter salary dump. The player taken with that pick? Desmond Bane, who is now firmly entrenched as a core player in Boston alongside Jayson Tatum and Jaylen Brown. The Celtics also never would’ve had to salary dump Walker in this scenario, either, meaning they’d have kept the 16th pick — which the Houston Rockets wound up using on promising young big Alperen Sengun. And Rozier would still be part of the mix too, as a solid guard off the bench.

What if the Brooklyn Nets’ Kevin Durant didn’t suffer a pair of knee sprains?

There is no shortage of what-ifs when it comes to the ultimately doomed triumvirate of Durant, Irving and James Harden in Brooklyn. However, if there is one thing that its collapse can be tied back to, it is Durant suffering the misfortune of opposing players falling into his legs.

In January 2022, it was New Orleans Pelicans forward Herbert Jones. In January 2023, it was Heat forward Jimmy Butler. In both cases, the consequences were severe.

In 2022, Durant’s absence saw the Nets fall apart, going 2-11 through the trade deadline as they fell from second to sixth in the East, which led to Harden forcing his way out of town. In 2023, the Nets went 6-9 through the trade deadline, leading to first Irving then Durant asking for — and receiving — trades away from Brooklyn.

It’s easy to assume something else would’ve befallen this group, given all that went on during their shared time together. But had Durant stayed healthy for either campaign, Brooklyn would’ve remained at the top of the East, the circumstances leading to Harden and Irving asking out of town never would’ve materialized and at least two of the three would likely still be in Brooklyn today — perhaps even having won a championship along the way.

What if the Charlotte Hornets’ Kemba Walker hadn’t made All-NBA in 2019?

When Walker, the best player in franchise history, made the All-NBA team in 2019, it left the Hornets with a massive decision: give Walker a supermax contract and keep him with a franchise stuck in neutral or let him leave in free agency. The latter happened, with Charlotte completing the sign-and-trade with Boston for Rozier, instead of paying Walker.

In this scenario, Walker doesn’t make All-NBA — which, in turn, makes it more palatable for Charlotte to re-sign him. Walker, who loved being in Charlotte, agrees to remain a Hornet and plays well enough in 2020 to prevent Charlotte from jumping up to get LaMelo Ball. Instead, the Hornets win the first-ever play-in game in the NBA bubble, before getting swept by the Milwaukee Bucks in the first round of the playoffs.

Walker’s knee would then fall apart, leaving a massive albatross of a contract on Charlotte’s books over the past three years. And with the second pick in this year’s draft, Charlotte would leap at the chance to take Scoot Henderson to supplant Walker as the face of the franchise as his contract expires.

What if Chicago Bulls guard Lonzo Ball’s knee wasn’t injured?

When Ball tore a meniscus against the Golden State Warriors in January 2022, the Bulls had the East’s best record. Without Ball, the Bulls collapsed down the stretch, getting routed in the first round of the playoffs by the Bucks last year, before losing in the play-in this past season. He is now unlikely to play during the 2023-24 campaign, as well.

With Ball still available, however, that never happens. The Bulls instead finish the 2022 season with the East’s best record and win a playoff series, before returning to the postseason this past season and being projected to do so again this coming season.

What if the Cleveland Cavaliers didn’t trade for Donovan Mitchell?

As the standoff between the Utah Jazz and New York Knicks dragged on last summer, the Cavaliers swooped in out of nowhere and made a stunning deal for the star guard instead. Mitchell then helped lead the Cavs to the playoffs for the first time without LeBron James in a quarter-century, at which point the Knicks ironically and emphatically ended their season in five games.

Without Mitchell, there is a much bigger share of the offense available to Evan Mobley, who instead of taking 12 shots per game for a second season in a row vaulted up to 18 attempts per game — scoring in the low 20s per game as a result and developing skills as both a passer and a perimeter shooter. The Cavaliers make it out of the play-in tournament and lose in the first round to Boston, but it’s a far more optimistic end to the season.

Cleveland, meanwhile, retains all of its draft capital going forward, keeping it as a prime player for any talent that considers shaking free around the league moving forward.

What if the Detroit Pistons drafted Tyrese Haliburton instead of Killian Hayes?

Since reaching the conference finals in six consecutive seasons, the Pistons have only been to the playoffs three times over the past 15 campaigns and have failed to win a single game. The foundation of the next playoff team in Motown, however, would’ve been set if Detroit had selected a different point guard prospect than Hayes in the 2020 draft.

By taking Haliburton seventh overall instead of Hayes, Detroit would have its floor general of the future. And when the Pistons leaped to the top of the lottery the following year and grabbed Cade Cunningham, they would have the perfect combination of size and skill at its two guard spots to complement each other for the rest of this decade — and beyond.

What if Indiana Pacers guard Victor Oladipo didn’t get hurt?

When the Pacers turned Paul George into Oladipo and Domantas Sabonis, it was a win-win deal for both sides. And when Oladipo nearly led the Pacers past LeBron James and the Cavaliers in the first round of the 2018 playoffs, it appeared Oladipo was set to be a pillar for the franchise — only for his career to be derailed by a torn quadriceps tendon in 2019.

A healthy Oladipo, meanwhile, has now made six consecutive All-Star teams and has remained one of the league’s elite guards. But the presence of Oladipo doesn’t prevent Indiana from making the swap of Sabonis for Tyrese Haliburton last year, giving them a different balancing of their roster around Oladipo and Myles Turner, as Indiana has firmly entrenched itself as a top-four team in the East.

What if the Miami Heat didn’t trade for Jimmy Butler?

The Heat missed the playoffs in three of the five seasons after LeBron James returned to Cleveland and only once won a playoff series. In the moment, it appeared they had no path to landing a player of Butler’s caliber — only for the Heat to manage to flip Josh Richardson to Philadelphia for Butler.

In this scenario, though, they do not. With Butler, the Heat made the NBA Finals twice and the conference finals three times. Without him, Miami flounders in the play-in mix over the past few seasons, failing to find the sort of star necessary to have the success the Heat have had with Butler and now has won just a single playoff series over the previous nine campaigns — a stretch that causes Pat Riley to finally step away from the franchise after more than a half-century in charge.

What if the Milwaukee Bucks didn’t sign Brook Lopez off the scrap heap?

When Lopez signed a $3.3 million deal with the Bucks in 2018, it was hard to envision what would lie ahead of him in Milwaukee. But Mike Budenholzer helped transform Lopez into a defensive menace, and the center’s entire career arc shifted.

Milwaukee, needing to find another answer without Lopez in the fold, instead winds up with Nerlens Noel, who fits poorly next to Giannis Antetokounmpo due to Noel’s lack of shooting.

The Bucks remain a threat in the East simply because of the presence of Antetokounmpo and Khris Middleton on the roster, but no Lopez means Milwaukee hasn’t ended its championship drought, and the noise surrounding Antetokounmpo’s future has grown louder by the year, culminating in him asking to be dealt away from the franchise this summer.

What if the New York Knicks drafted Tyrese Haliburton instead of Obi Toppin?

The Knicks have slowly but surely built up their talent base under president of basketball operations Leon Rose. There is, however, one significant mistake: picking Toppin over Haliburton in the 2020 draft.

Toppin has been a bit player the past three years in New York, while Haliburton has blossomed into one of the game’s brightest young stars. Under this scenario, the Knicks still had the money to sign Jalen Brunson this past offseason, and the Brunson-Haliburton combo would fit together perfectly.

And with Haliburton, the Knicks would be good enough to take down the Heat in the conference semifinals, before losing to the Celtics in the conference finals — all while still having their current cache of young players and draft capital to add another star whenever one shakes free.

What if Orlando Magic forward Jonathan Isaac never injured his knee?

As a rangy, 6-foot-11 forward, Isaac was beginning to look like a modern-day version of Andrei Kirilenko — a truly dynamic talent.

Then came a left knee injury suffered on Jan. 1, 2020. That began a series of injuries that has caused Isaac to play in just 13 of Orlando’s 275 games over the past three-plus seasons.

But what if he hadn’t gotten hurt? The idealized, healthy version of Isaac would be a perfect complementary player in Orlando’s frontcourt — particularly next to Paolo Banchero, as Isaac would take on the top defensive assignment while Banchero would perform the heavy lifting at the other end.

What if the Philadelphia 76ers kept Jimmy Butler?

To say moving on from Butler in the summer of 2019 was a disastrous decision is an understatement. Al Horford and Josh Richardson were both awful fits in Philadelphia, with each lasting exactly one season. Butler, meanwhile, has led the Heat to the NBA Finals twice and to the conference finals three times since he left the Sixers.

So how would things look had Butler stayed in Philly? The Sixers, instead of the Heat, would be the dominant team in the East behind Butler and Embiid. By keeping Butler, it would signal the end for Ben Simmons in Philadelphia, as the 76ers would ship him out in a deal for Kyle Lowry and future assets the following season, well before Simmons’ disastrous series against the Hawks in 2021, and Philadelphia would reach the NBA Finals in 2021 — instead of Milwaukee — and end the city’s near four-decade title drought.

What if Kawhi Leonard stayed with the Toronto Raptors after their title?

The Raptors got everything they could’ve hoped for from Leonard in his one season north of the border. They just couldn’t convince him to stay there.

But what if they had? Toronto was good enough to win the title in the NBA bubble in 2020 without Leonard; instead, it lost a conference semifinals heartbreaker in seven games to Boston while Pascal Siakam had a subpar series. With a healthy Leonard in tow, the Raptors would repeat as champions in Orlando. And in turn, the entire core group that has slowly splintered off the past few years — including Kyle Lowry, Fred VanVleet and coach Nick Nurse — would all still be in Toronto, and the Raptors would still be a bona fide title contender.

What if the Washington Wizards traded Bradley Beal two years ago?