The Portland Trail Blazers are in the middle of a pivotal offseason. Many knew from the start that the Blazers were in for a huge offseason, on the clock as they were to surround Damian Lillard with the pieces necessary for the team to compete for a championship. Instead, the Blazers stood pat and selected Scoot Henderson with the third overall pick of the 2023 NBA Draft. As a result, Lillard has now requested a trade, even squeezing the Blazers dry by singling out the Miami Heat as his preferred destination.

Lillard's trade request certainly threw a major curveball in the Blazers' offseason plans. In fact, it's very obvious that the Blazers did not envision Lillard wanting out, and as a result, they made a decision in free agency that could be a difficult one to shake off for the foreseeable future.

One move stands out as the Blazers' biggest mistake during the 2023 NBA free agency, and here's what it is.

Blazers' biggest mistake during 2023 NBA free agency: Signing Jerami Grant to a five-year, $160 million contract

The Blazers acquired Jerami Grant during the 2022 offseason with the intention of giving Damian Lillard a two-way weapon on the wing, helping improve the defense as well as easing the offensive burden on their star point guard's shoulders.

And for the most part, Grant did his job for the Blazers. He averaged 20.5 points per game on an incredible true shooting percentage of 60.6, giving the team everything they hoped for when they dealt away a low-end first-round pick and two second-rounders for his services.

Thus, it stood to reason that the Blazers would do everything in their power to keep Jerami Grant in town, especially when doing so could help persuade Damian Lillard to stick it out with the team for the long haul. So to begin free agency, the Blazers were active, re-signing Grant to fulfill step one in their quest to keep their best player.

The price the Blazers paid, however, caused some jaws to drop around the league. They ended up signing Grant to a five-year, $160 million deal, which is an incredible amount of money even for a player of his quality. But the Blazers couldn't afford to lose him, so they did not dilly-dally and negotiated a contract quickly with the 29-year-old forward.

Even then, keeping Jerami Grant was not a surefire way to retain Damian Lillard as well. And the Blazers learned that the hard way when Chris Haynes of Bleacher Report announced that Lillard has requested a trade from the franchise the very next morning after Adrian Wojnarowski of ESPN reported that Grant had re-upped with the Blazers.

With Lillard on the way out, paying $32 million for Grant, a player who suits more of a complementary role, became even more questionable for the Blazers. With a rebuild on the horizon, it certainly seems like that is not the most ideal allocation of funds.

Others would argue that the Blazers could just decide to trade away Jerami Grant, adding to their treasure chest of future draft assets. But given the harsher penalties brought forth by the new CBA, will any contending team be able to stomach trading for Grant and his hefty contract?

During this offseason alone, some teams have already made moves with the fear of having to deal with difficulties of matching salaries in trades or being restricted from using cash in deals, or the other severe penalties that come with crossing the second luxury tax apron in mind. The Golden State Warriors, for example, traded away Jordan Poole to ease the financial burden on their future books, while the Miami Heat refused to trade for Bradley Beal due to similar concerns.

By the end of Grant's contract, his perception could end up being similar to that of Tobias Harris. Harris, like Grant, is a 20-points-per-game scorer. But on their own, they do not guarantee the success of a team. Grant's stint as a leading scoring option for the Detroit Pistons bore fruit, for sure, but fruit in the form of the first overall pick of the 2021 NBA Draft (Cade Cunningham).

Nevertheless, with Scoot Henderson looking like he's ready to fill in Damian Lillard's shoes, Grant could help usher in a new era of success in Portland. With Henderson, Anfernee Simons, and Shaedon Sharpe all looking like future stars, Grant's two-way contributions should be a huge boon for the franchise as they go through this transitional period. So it's not the end of the world for them. But certainly, they'll be wondering whether this was the best way they could have spent $160 million.