Which 2023 NBA Offseason Moves Will Look Worst In 3 Years?

After first examining the 2023 offseason moves that will look the best in three years, it's time to predict which will turn out to be the biggest mistakes.

So far, last year's predictions are looking strong, with the Rudy Gobert trade and the Washington Wizards giving Bradley Beal a no-trade clause topping the 2022 list.

From some massive overpays, a star guard making the wrong choice with his player option and a trade that has doomed a franchise's future finances while removing a key starter, these are the 2023 moves that will look the worst in three years.

Most of the time, cap space is a good thing. Sometimes, like with the 2023 Houston Rockets, it can cause you to wildly overspend on players, using the money just because you have it.

The NBA's new collective bargaining agreement mandates that teams must spend at least 90 percent of the salary cap before the regular season begins. However, the Rockets made some real questionable signings with their $60-plus million of salary-cap space.

While the Fred VanVleet contract was a little wild (three years, $128.5 million with a third-year team option), Houston needed a point guard, veteran leader and culture setter. It was an overpay, but he'll make the rest of the young Rockets better.

On the other hand, giving Brooks $80-plus million was the worst contract handed out in free agency, especially when the final number turned out to be $86 million over four years.

The primary problem with Brooks is that he's a defensive specialist who thinks he's an offensive specialist. Of the 74 NBA players who attempted at least 13 shots or more per game last season, Brooks' true shooting mark of 49.4 percent ranked dead last.

Going from a championship-hopeful Memphis Grizzlies team to a young Houston Rockets squad coming off a 22-win season likely won't scale back Brooks' shot selection, either. The Rockets already ranked last as a team in three-point efficiency (32.7 percent) and 28th in overall field-goal percentage (45.7 percent) this past season.

There's no team option or partial guarantee in these four years to get Houston out of Brooks' contract earlier, either. Every shot he takes away from players like Jalen Green, Jabari Smith Jr., Alperen Şengün, Amen Thompson, Tari Eason and others will only hinder the progress of what could be one of the best young cores in the NBA.

Getting Brooks on a one- or two-year deal at a mid-level exception-type salary would have been understandable. Paying him $20-plus million a year into his 30s doesn't make sense for a Rockets team that needs to create shot opportunities for its younger group instead.

Thought to be the best free agent on the market this offseason, Harden surprised the league when he opted into his $35.6 million player option instead.

A month earlier, ESPN's Brian Windhorst said there was a chance Harden could land a four-year, $200 million contract as an unrestricted free agent. Harden had previously turned down a three-year, $161 million extension from the Brooklyn Nets in 2021 as well.

With Harden set to turn 34 in August, this summer might have been his last chance to sign a max-level contract. Choosing to play on an expiring $35 million deal while now being ineligible to sign an extension is a potentially costly move for Harden, one which he'll almost certainly regret three years from now.

Harden's decision to take less money in order to be traded immediately hasn't worked out thus far, and there are no immediate deals on the horizon, either. Joel Embiid hopes he changes his mind. New teammate Patrick Beverley wants him to as well.

Outside of the Los Angeles Clippers, not many teams make sense as a Harden landing spot. That means the 2017-18 MVP might have to return to Philly with his tail between his legs.

Players typically don't increase their value year-over-year in their mid-30s, which Harden is going to find out the hard way. He should have taken the Brooklyn extension, negotiated a long-term deal with the Sixers or at least tried to work out a sign-and-trade this offseason.

No team is likely to offer Harden $200 million on a new deal next summer. Opting in was a big mistake.

Kyrie Irving has averaged fewer than three seasons with his teams since requesting a trade from the Cleveland Cavaliers in 2017. It thus wouldn't be a surprise if he grows tired of the Mavs (or vice versa) before the end of his new three-year, $126 million contract

Irving getting over $40 million per season from Dallas was a work of art by his agent and stepmother, Shetellia Riley Irving, especially since she negotiated a third-year player option as well.

It was fair to wonder whether Irving's guaranteed money would be affected by his lack of availability in recent years, but it hardly mattered in the end. Irving's contract has $120 million in guaranteed money, with only $6 million tied to incentives. Irving will collect an extra $1 million each season if the Mavs win at least 50 games and another $1 million if he plays in 65 or more games.

This was a desperate move by the Mavericks, who were desperate not to lose another star guard in free agency. Unlike with Jalen Brunson, however, no other team was likely to give Irving this kind of money.

Something will eventually affect Irving's availability. We just don't know what yet.

Tying perhaps the most unpredictable player in the NBA to Luka Dončić is a dangerous game to play for Dallas, a franchise that is still widely carried by its Slovenian superstar. If (when?) Irving grows unhappy or becomes a distraction, the Mavs can only hope that Dončić doesn't ask out as well.

On paper, getting Kristaps Porziņģis and two first-round picks for Marcus Smart looks like good value. Porziņģis is coming off a strong season, can be a third offensive option and rim protector for Boston and helps to better balance out the roster.

Dive deeper into the trade, however, and this is a massive gamble for the Celtics.

Losing Smart, their starting point guard and an integral part of their success for the past nine seasons, is huge in a number of areas. Once referred to as "the heart and soul of this team" by Jaylen Brown, Smart was Boston's best passer and only one season removed from winning Defensive Player of the Year. He gets the Celtics into their offensive sets, calls teammates out if necessary and can start fires when they clearly need a spark.

When Smart, Jayson Tatum and Brown all shared the floor this postseason, the Celtics had a net rating of plus-7.4 (90th percentile, per Cleaning the Glass). When the two star forwards were on the court without Smart, that number tumbled to minus-0.9 (47th percentile).

The Celtics will miss both Smart's presence on the court and in the locker room. This trade will have a major impact on their finances as well.

While Smart was owed a team-friendly average of nearly $20 million per year for the next three seasons, a two-year, $60 million extension for Porziņģis brings his total to $96 million over the next three seasons. That's $12 million more per year than Smart, which is significant when taking a look at Boston's financial future.

If Tatum and Brown each sign their expected $300-plus million extensions, the Celtics are going to become one of the NBA's most expensive rosters moving forward. Malcolm Brogdon is making $22.5 million each of the next two seasons, and Derrick White is making roughly $19 million per year over that span as well.

Boston is destined to become a second-apron team, which will put limitations on their future trades and draft picks. With Porziņģis averaging only 54 games per season over the past four years since returning from a torn ACL, durability will continue to be a major concern moving forward.

This trade may look fine now, but it has the potential to turn disastrous in a few years.

Who among us expected Jerami Grant to sign the NBA's largest contract in free agency?

Grant's $160 million in total money tops Fred VanVleet, Kyrie Irving, Khris Middleton and others. He was the only player to sign a five-year deal as well.

Perhaps the Blazers did this so they didn't lose a valuable player for nothing, locking Grant in with the hopes of turning him into a trade chip later. The 2018 Cleveland Cavaliers did the same with Kevin Love by giving him a four-year, $120 million extension, which became untradeable almost immediately as Love crossed into his 30s.

In three years, Grant will be 32 and will still have two seasons and $70 million remaining on his contract, including a $36.4 million player option in 2027-28. He's essentially being paid like a No. 1 or No. 2 option, yet he's probably the fourth-best player on a championship-caliber team. According to ProFitX.com, Grant's real-time contract this past season was valued at $19 million.

Portland has to hope that Grant gets off to a strong start to the 2023-24 seasons, eating up more shot opportunities following a Damian Lillard trade. The Blazers should try to move off his contract as soon as possible, even if the ink is still drying.