For NBA teams, every contract they sign carries a certain amount of risk, and they generally want to avoid disastrous contracts.
Unfortunately, no one is perfect.
Over the past five years, teams have spent tens, if not hundreds, of millions of dollars on standout players who they believe will become cornerstones of their future and contend for championships.
But fast forward a few years and that best-case scenario vision may fade away, as declining production, roster fit issues and a number of other influences could make the deal an eyesore.
The list below is subjective, but factors in players who have signed contracts worth more than $70 million since 2019.
Contract: Five years, $180 million, signed in 2019
Tobias Harris was acquired at the 2019 trade deadline and quickly signed a near-max contract extension with the Philadelphia 76ers. He seemed like the ideal wing to complement rising stars Joel Embiid and Ben Simmons.
There's a lot to interpret in this sentence, isn't there?
Philadelphia was hoping this trio would be a big success, but it just didn't work out. More on Simmons later.
Harris consistently averaged over 17 points per game during his contract, but his development stagnated and he faltered in the postseason. Injuries to Embiid gave Harris a few chances to briefly become a top player, but he never reached that level.
The Sixers are not expected to re-sign Harris when he becomes an unrestricted free agent in July 2024.
Contract: Five years, $170 million, signed in 2019
About two weeks later, the Sixers made the obvious decision to sign Ben Simmons to a maximum contract extension.
The versatile guard missed his first season with an injury but won Rookie of the Year honors in 2017-18. Simmons went on to be an All-Star, so it was an easy decision for Philadelphia given his resume. He also earned All-Defensive and All-NBA Third Team honors in each of his next two seasons.
But the nightmare began in 2021.
First, Simmons had a memorable pass-through dunk in a Game 7 loss to the Atlanta Hawks, a turmoil that led to Simmons asking for a trade, sitting out training camp or the preseason, being suspended for the season opener, and eventually being traded to the Brooklyn Nets.
Simmons missed the rest of the season with a back injury that recurred, and played just 57 games over the next two years, including just 15 in the 2023-24 season.
The deal expires after the 2024-25 season.
Contract: 4 years, $120 million, signed in 2020
It's never a good thing for a contract to be criticised so quickly, and you can't argue against the benefit of hindsight.
The Charlotte Hornets aren't exactly a destination team, so it's understandable why they offered Gordon Hayward a big contract, encouraged him to bounce back after injury, and tried to build a competitive roster around LaMelo Ball and co.
(For a quick technical explanation, Charlotte acquired Hayward in a sign-and-trade with the Boston Celtics, but the Hornets handled the contract negotiations.)
That said, health issues have characterized his tenure in Charlotte.
Hayward played fewer than 50 games each season with the Hornets and his points dipped from 19.6 to 14.5, and Charlotte dealt him to the Oklahoma City Thunder as part of a 2024 payroll reduction for both teams.
Incidentally, the next guy traded places with Hayward.
Contract: Five years, $80 million, signed in 2020
Davis Bertans carved out a valuable role as a backup shooter for the San Antonio Spurs early in his career. During the 2018-19 season, he took a ton of three-pointers, connecting on 42.9% of them.
However, San Antonio went in a new direction, with the Washington Wizards acquiring Bertans.
He was given the green light in his first season with Washington, where he averaged 15.4 points on 8.7 3-pointers per game, nearly doubling his previous career high of 8.0 points per game, and he parlayed that career-best year into a long-term extension with the Wizards.
Oops.
Bertans remains a long-distance threat, but his overall limitations remain the same: He has since left the Wizards for the Dallas Mavericks, Thunder and Hornets and has not played more than 15.7 minutes per game in any of the past three seasons.
Bertans is under contract through 2024-25, with $5.25 million of his $16 million guaranteed, and could be released at some point this offseason following a cap-clearing trade.
Contract: 4 years, $73 million, expiry date 2021
The following summer, the New York Knicks took a similar risk.
Evan Fournier has always been recognized for his prowess on the perimeter throughout his nine seasons in the NBA, where he has shot 37.9% from three-point range as a high-volume option, including a career-best 41.3% in 2020-21.
New York had a chance to compete for the championship after ending an eight-year playoff drought that season, and while there are legitimate questions about whether the Knicks should have prioritized a true point guard, Fournier was a capable shooter.
But within a year, he was forgotten.
Fournier was out of the starting rotation in 2022-23 and is not expected to return to the starting rotation in 2023-24 after playing a combined 498 minutes in New York over those two seasons and making more than $18 million each year.
After sitting on the bench for a very expensive transfer, the Knicks dealt him to the Detroit Pistons at the 2024 trade deadline.
Contract: Five years, $251 million, expiry date 2022
On the bright side, the Wizards were able to get Bradley Beal out of his contract after just one season, and while Washington deserves criticism for offering him the contract, that's now the Phoenix Suns' problem.
And that's a capital P problem.
Two years into his contract, Beal has missed at least 29 games in each season, a worrying trend as the veteran guard approaches the prime of his career.
Beal's remaining three salary cap numbers are more than $50 million each, making a move virtually impossible.
Beal waived his no-trade clause when he left the Wizards, likely because Phoenix was the more competitive team, and it's not unreasonable to say that if the Suns don't perform well soon, Beal probably isn't playing at an All-NBA level and his salary makes him less attractive on the trade market.
Contract: 4 years, $140 million, expiry date 2022
Jordan Poole played a key role in the Golden State Warriors' journey to winning the 2021-22 NBA title, and his breakout year came at the perfect time, as he was eligible to sign a rookie-scale extension.
“Poole has proven to be a valuable addition to the Warriors' offense. Scorers get rewarded, and Poole can score,” B/R's Eric Pincus wrote at the time. “Could he be the complete player?”
Draymond Green's punch changed everything.
Instead of being able to thrive in a great environment, Poole had to walk on figurative eggshells for a year in Golden State. It clearly became too much to bear, and the Warriors traded him to the Wizards before the 2023-24 season. Not surprisingly, his efficiency declined while starring for one of the worst teams in the league.
This is a long-winded statement that Poole's contract might actually be more manageable if he were still with Golden State, but it's not as friendly as Washington's leading scorer.
