The NBA offseason is a time of big moves and risky decisions as teams aim to strengthen their rosters and boost their chances of success. But not every signing hits the mark, and some end up being regrettable choices. In this article, we’ll take a look at ten moves from last summer that left teams and fans scratching their heads. From contracts that didn’t live up to the hype to deals that turned out to be costly mistakes, these regrettable signings serve as cautionary tales in the fast-paced world of professional basketball.
1. Fred VanVleet

Fred VanVleet’s departure from the Toronto Raptors in the 2022-23 NBA season marked a significant shift in his career trajectory. With impressive averages of 19.3 points, 7.2 assists, and 4.1 rebounds per game, VanVleet had established himself as a valuable asset on the court. Yet, his move to the Houston Rockets in the following offseason raised eyebrows across the league.
Houston, eager to bolster their roster, secured VanVleet with a maximum contract for the 2023-24 season, with a 3-year, $128 million contract, placing high expectations on the seasoned guard. Fans and analysts alike anticipated VanVleet’s arrival to elevate the Rockets’ performance and potentially propel them into playoff contention.
Yet, as the season progressed, it became evident that VanVleet’s impact on the Rockets was not as transformative as hoped. Despite his commendable averages of 16.8 points, 8.2 assists, and 3.7 rebounds per game, along with a respectable 41% field goal percentage, the Rockets found themselves languishing in the lower echelons of the Western Conference standings.
The disappointment stemming from VanVleet’s underwhelming performance in Houston was compounded by the perception that the Rockets had overpaid for his services. With a maximum contract in hand, expectations were high for VanVleet to justify his price tag with stellar play and tangible results on the court. Still, the reality fell short of these lofty expectations, leaving many to question the wisdom of Houston’s investment.
Moreover, the context of VanVleet’s underperformance is particularly glaring when juxtaposed with the competitive landscape of the NBA. While teams like the Indiana Pacers, Orlando Magic, and the Oklahoma City Thunder actively vie for playoff contention, the Rockets find themselves on the fringes, unable to make a significant impact in the highly competitive Western Conference.
2. Jerami Grant

Jerami Grant’s decision to re-sign with the Portland Trail Blazers on a blockbuster 5-year, $160 million contract this offseason sent shockwaves through the NBA community. Nevertheless, what was initially seen as a commitment to bolstering the team’s roster quickly morphed into a cautionary tale of overpaying.
Grant’s return to Portland came at a time of uncertainty for the franchise, with the departure of their star player, Damian Lillard, looming large. Despite the opportunity to construct a competitive roster around Lillard, the Blazers opted to invest a staggering amount of money in Grant, a move that many viewed as an excessive overpay for a player whose value did not align with the price tag.
Moreover, the ramifications of Grant’s contract extend beyond the basketball court, as the financial burden it imposes could complicate the Blazers’ efforts to build a competitive team in the future. With the team struggling to find its footing in the Western Conference and facing limited flexibility in terms of roster moves, Grant’s contract looms large as a potential impediment to future success.
In hindsight, the decision to invest heavily in Grant (21.0 PPG, 3.5 RPG, 2.8 APG) at the expense of building a well-rounded roster around Lillard proved to be a costly misstep for the Blazers. As Lillard ultimately departed for the Milwaukee Bucks, the consequences of the team’s misplaced priorities became painfully clear, serving as a stark reminder of the perils of overpaying for talent in the NBA.
3. Gabe Vincent

Gabe Vincent’s journey from the Miami Heat to the Los Angeles Lakers was met with anticipation and high hopes, especially considering his impressive performance in the 2023 playoffs. During his time with Miami, Vincent showcased his abilities on the grandest stage, averaging 12.7 points, 3.5 assists, and 1.4 rebounds per game while shooting an impressive 38% from beyond the arc in 22 playoff games.
Amidst the hype, his transition to the Lakers has been far from smooth. Vincent struggled to find his rhythm in Los Angeles, averaging just 5.4 points per game, a significant drop from his playoff performance with Miami. Furthermore, his season was marred by injury, with Vincent facing the risk of missing the remainder of the season due to his ailment.
Vincent’s inability to make a significant impact on the court has rendered him a non-factor for the Lakers, raising questions about the wisdom of his acquisition for 3 years and $33 million. With the team grappling with injuries and inconsistency, Vincent’s underwhelming performance has only added to their woes, leaving fans and analysts alike scratching their heads.
As Vincent faces the prospect of an extended absence from the court, the Lakers find themselves in a precarious position, lacking the depth and firepower needed to compete at the highest level. While injuries are an unfortunate reality of professional sports, Vincent’s inability to live up to expectations has only compounded the challenges facing the team.
4. Seth Curry

Seth Curry’s homecoming to the Dallas Mavericks, where he previously enjoyed some of his best performances, was met with optimism and anticipation from fans and analysts alike after signing an $8 million deal.
Yer, his second stint with the Mavericks failed to live up to expectations, with Curry struggling to make a significant impact on the court.
Despite his previous success in Dallas, Curry’s statistics this season were underwhelming, averaging just 5.1 points, 1.5 rebounds, and 1.0 assists per game across 39 games. His inability to find his rhythm and contribute consistently left many questioning the wisdom of his return to the Mavericks.
Ultimately, Curry’s lackluster performance prompted the Mavericks to make a move, trading him to the Charlotte Hornets as part of a deal that also involved Grant Williams. In exchange, the Mavericks acquired PJ Washington, hoping to inject new energy and versatility into their lineup.
5. Jarred Vanderbilt

Jarred Vanderbilt’s tenure with the Los Angeles Lakers started on a promising note, with the forward showcasing his defensive prowess following a trade that brought him from Utah. Yet, this season, after signing a new four-year, $48 million contract extension with the Lakers, Vanderbilt’s performance on the offensive end has been less than stellar.
In the previous season, Vanderbilt established himself as an excellent defender for the Lakers, earning praise for his defensive intensity and versatility on the court. Still, his offensive contributions have left much to be desired this season, averaging just 5.2 points, 4.8 rebounds, and 1.2 assists per game, with less than 4.0 field goal attempts per contest.
Vanderbilt’s struggles on offense have made him a liability for the Lakers, particularly as they seek consistency and production from their role players. While his defensive abilities remain valuable, his inability to contribute effectively on offense has hindered the team’s overall performance and offensive flow.
As the Lakers navigate the challenges of the season, Vanderbilt’s underwhelming offensive output underscores the importance of balance and contribution from all players on the roster. While his defensive contributions cannot be overlooked, Vanderbilt will need to find ways to improve his offensive game to truly make an impact for the Lakers moving forward.
6. Dwight Powell

Dwight Powell’s contract renewal with the Dallas Mavericks was met with some optimism, as the team sought to retain his services for the upcoming season. Nevertheless, his role on the team has shifted significantly, with Powell finding himself relegated to a backup role behind rookie Derek Lively II, Daniel Gafford, and PJ Washington.
Despite his tenure with the Mavericks and previous contributions to the team, Powell’s production has declined this season. Averaging just 3.5 points, 3.3 rebounds, and 1.4 assists per game, Powell has struggled to make a significant impact on the court.
With the emergence of younger talent and the team’s desire to develop its prospects, Powell’s minutes have diminished, and he has been tasked primarily with providing depth off the bench. While his experience and veteran leadership may still hold value for the Mavericks, Powell’s reduced role reflects the team’s shifting priorities and focus on youth development.
7. Malik Beasley

Malik Beasley’s transition from the Los Angeles Lakers to the Milwaukee Bucks placed him in a contender’s environment alongside stars like Giannis Antetokounmpo and Damian Lillard. Yet, despite the Bucks’ formidable roster, Beasley’s defensive shortcomings have emerged as a significant concern.
Joining a team with aspirations of championship glory, Beasley’s defensive contributions have fallen short of expectations. His struggles on the defensive end have raised questions about his fit within the Bucks’ lineup, particularly given the presence of Lillard in the backcourt. Many observers argue that the Bucks should have pursued a more defensively-minded shooting guard to complement Lillard’s offensive prowess and shore up their defense.
While Beasley (11.6 PPG, 42.8 3P%) brings offensive firepower to the Bucks, his defensive deficiencies have made him a liability on the court, particularly in high-stakes matchups against elite opponents. As the Bucks strive to solidify their position as contenders in the Eastern Conference, addressing their defensive vulnerabilities will be crucial to their success in the postseason.
8. Yuta Watanabe

Yuta Watanabe followed Kevin Durant to the Phoenix Suns, joining a star-studded lineup featuring Durant, Devin Booker, and Bradley Beal. Despite an impressive 44.4% 3-point shooting with the Brooklyn Nets last season, Watanabe has struggled to replicate his success in Phoenix.
Expectations were high for Watanabe upon his arrival, but his performance on the court has fallen short. Averaging just 3.4 points, 1.6 rebounds, and 0.4 assists per game while shooting a mere 30% from beyond the arc, he has failed to make the desired impact.
His difficulties in finding his form raised questions about his fit within the Suns’ system and his ability to contribute effectively alongside the team’s star players. Despite his past success, Watanabe eventually got traded to the Grizzlies at the deadline.
9. Khris Middleton

Khris Middleton’s renewal with the Milwaukee Bucks for three years and $102 million raised eyebrows league-wide. His performance this season has failed to meet expectations, sparking doubts about the justification of his hefty contract.
Expected to be a cornerstone alongside Giannis Antetokounmpo and Damian Lillard, Middleton’s contributions have fallen short. With averages of just 15.0 points, 5.2 assists, and 4.4 rebounds per game, he has struggled to make a significant impact on the court.
Middleton’s underwhelming performance prompts questions about his value to the team and the rationale behind his renewal. As the Bucks vie for success in the competitive Eastern Conference, Middleton must elevate his game to meet expectations.
As the season unfolds, Middleton faces pressure to prove his worth and justify the Bucks’ faith in him. With championship aspirations at stake, Middleton must rediscover his form and contribute meaningfully. Otherwise, his lucrative renewal may be viewed as a misstep for the franchise.
10. Caris LeVert

Caris LeVert’s renewal with the Cleveland Cavaliers came on the heels of an impressive 2022-23 season. However, this season has seen a significant dip in his efficiency, with LeVert averaging just 13.7 points and 5.3 assists per game while shooting at 41.0% from the field and 31.7% from beyond the arc.
Following his stellar performance in the previous season, expectations were high for LeVert to continue his trajectory of success. His struggles to maintain consistency on the court have been evident, leading to questions about the wisdom of his renewal.
As a key contributor for the Cavaliers, LeVert’s decline in efficiency has raised concerns about his impact on the team’s performance. With aspirations of competing at a high level, the Cavaliers need LeVert to rediscover his form and contribute more effectively on both ends of the floor.
As the season progresses, LeVert will need to address his shooting woes and find ways to elevate his game. With the Cavaliers’ playoff hopes hanging in the balance, LeVert’s ability to bounce back from his struggles will be crucial to their success in the competitive Eastern Conference.