The Portland Trail Blazers' offseason is just getting started. In the aftermath of Damian Lillard's request that he specifically be traded to the Miami Heat, the Blazers will be weighing their options on the trade front. Will they accommodate Lillard's request, or will they hold out for the best deal possible from any team?

Whatever the case may end up being, one thing's for sure: how the Blazers deal with the Lillard situation will affect the franchise for years to come. In fact, Lillard already affected the Blazers' dealings in free agency in a huge way.

In a bid to keep their star point guard in town, the Blazers re-signed Jerami Grant to a five-year, $160 million deal, which is definitely an expensive contract to pay even for a player of his caliber. However, shortly thereafter, Lillard's trade request became public knowledge, so it may not have been the best move for the Blazers to sign Grant to that huge of a contract.

Still, one could argue that it was better to sign Grant to that deal instead of losing him for nothing. Clearly that was the Blazers' mentality when they also brought back Matisse Thybulle on a three-year, $33 million deal, matching the Dallas Mavericks' offer sheet for the lockdown perimeter defender.

All in all, how do the Blazers' dealings look nearly two weeks into free agency? Here are grades for the Blazers' signings thus far.

Blazers free agency grades

Re-signing Jerami Grant to a five-year, $160 million deal: C

Had the Blazers waited just a few hours…

Look, it's unfair to rag on the Blazers' decision to bring back Jerami Grant too much. Grant, for all his deficiencies (mostly rebounding), is a quality player to have. Every team wishes they have their own version of the 29-year old combo forward — a player who guards multiple positions, provides some weakside rim protection, and someone who can create shots for himself at the perimeter to ease the offensive burden that the team's star is carrying.

However, at $32 million a year, Grant's signing will certainly raise a few eyebrows, especially with the Blazers entering a rebuild. This contract makes trading Grant away difficult, as teams will be wary of taking on deals like these given the harsh penalties of dipping into the second luxury tax apron under the new CBA.

And for a player who projects as more of a complementary piece, a tertiary option on a contending team, $32 million may be too expensive a price anyway for contending teams to take on in the first place.

Thus, the Blazers may be stuck with Jerami Grant for years to come. Now that's not necessarily a bad thing. Grant will help Anfernee Simons, Scoot Henderson, Shaedon Sharpe, and whomever the Blazers receive for Damian Lillard immensely. But had the Blazers waited for the Lillard domino to fall before committing to anything in free agency, keeping Grant may not have cost them this much money.

Alas, all the Blazers can hope for now is that Grant remains healthy and consistent for the next five years to help transition the team from one phase to another.

Re-signing Matisse Thybulle to a three-year, $33 million deal: B

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Peter Sampson ·

The Blazers did well when they acquired Matisse Thybulle in the trade that sent Josh Hart to the New York Knicks. Thybulle may have been in the final year of his deal, but he gave the Blazers a defensive specialist, a player who racks up steals and blocks like he puts up quality vlogs.

Before landing with the Blazers, Thybulle struggled to earn a solid role for the Philadelphia 76ers during the 2022-23 season. But he turned things around almost immediately in Portland. In 22 games with the Blazers, he put up 11 outings with multiple threes including games with four and five makes from beyond the arc. Thybulle's progression from deep, having shot a career-high 38.8 percent from three with the Blazers, bodes well for his ability to contribute to a winning team, given his incredible defensive acumen.

But with the Blazers entering a rebuild, Thybulle may find it difficult to contribute as much as he could to a winning team. Given his limitations as an offensive player (lack of shot creation, dribbling, playmaking, and non-elite rim finishing), he would have been a better fit in Dallas.

And rumor has it that Thybulle preferred to land with the Mavs. In fact, the verbiage of the reporting stated that he “desperately” wanted to play alongside Luka Doncic and Australian compatriot Josh Green.

In terms of an asset management standpoint, keeping Matisse Thybulle in town was the best decision, especially when he didn't sign too expensive of a deal anyway. Not letting him leave for the Mavs for nothing in free agency was a wise move in that respect.