Why not continue to mess up? Tuoji: Wrong! Judging from the draft picks, the Blazers should win now

Translator's Note: This article was originally published by SBNation and the author is Dave Deckard. The data in the article are as of the time of publication of the original article (November 12, local time). The opinions in the article have nothing to do with the translator and the platform.

Why "win now" is the only answer for the Trail Blazers

In Portland, playing bad is no longer a viable option. The Trail Blazers got off to a 5-5 start in the 2025-26 NBA regular season. This record is an improvement over recent years, especially since it also included iconic wins over the Thunder and Nuggets. But a 50% winning rate is only a way station on the road to success, not the end. The Trail Blazers' inconsistent performance has left fans asking: Should this team no longer settle for mediocrity and instead be like the legendary woodchuck that sees its own shadow and then hides in its hole for six weeks (or months) of winter? This is exactly the topic that this issue of the Trail Blazers Fan Mailbox will discuss.

Fan Letter:

I love this new Trail Blazers team as much as anyone, but let’s not kid ourselves. The team's final record was still not up to par. We all know that in the NBA, falling into mediocrity is the worst possible situation. If we're not destined to win the championship this year, wouldn't it be smarter to at least mess up for another year? This team still needs talent, and the draft is the best way to add that, right?

There is some truth to your point, especially since the 2026 NBA Draft is considered a big draft year, but there is a key factor to consider.

As early as 2021, the Trail Blazers traded a first-round pick to the Bulls in exchange for forward Larry Nance Jr. But fortunately, the Trail Blazers thought carefully at the time and added lottery protection clauses to this pick. Since the Trail Blazers have entered the lottery each of the past four years, this pick has yet to be shipped to the Bulls.

Between now and 2028, as long as the Trail Blazers get out of the lottery for the first time, the Bulls will receive this first-round pick. Prior to this, the obligations of this transaction had not been fulfilled.

The good news is that if this obligation is not fulfilled by 2028, the pick will become a second-round pick, which will be much easier for the Trail Blazers to accept.

But the bad news is that a sticky situation may arise during this period.

In 2023, when the Trail Blazers traded Damian Lillard to the Bucks, one of the rewards they received was the right to exchange draft picks with the Bucks in the 2027 NBA Draft. At the time, it seemed like a risky deal. The Trail Blazers are in the midst of a deep rebuild, and the Bucks landed one of the league's top guards. As things stand at the time, the Trail Blazers are likely to have a better draft pick than the Bucks in 2027 due to their own strength, which makes the swap rights useless.

But the situation changed during this period. The Trail Blazers are improving, the Bucks, while still strong, have waived Lillard, and there's almost monthly talk about whether they'll trade Antetokounmpo to start a rebuild. If Antetokounmpo no longer plays for the Bucks in 2027, the Bucks' draft picks may become extremely valuable, possibly even No. 1 overall. The Trail Blazers hold the rights to swap with them.

However, there is a point that needs attention here. A nightmare scenario may be looming.

Remember that draft pick owed to the Bulls? If the Trail Blazers fail to make the playoffs in 2026, lottery protection will remain in effect. The Trail Blazers will retain their draft rights and the trade obligations will be deferred until 2027.

But 2027 is the year of exchanging draft picks with the Bucks.

Assume that by then, the trade obligations with the Bulls remain unfulfilled. In this case, if the Trail Blazers fail to make the playoffs again in 2027, that's fine. Lottery protection will remain in effect, they will retain their pick, and they can still exercise the swap option if the Bucks pick higher.

But if the Trail Blazers improve in strength and successfully enter the playoffs in 2027, their first-round pick will be sent to the Bulls. And if there is no first-round pick, the Trail Blazers will have no assets that can be exchanged with the Bucks, which will cause the draft pick swap agreement to become invalid. They could only watch as the Bucks selected a rookie in the lottery, and this pick might have belonged to them - the root of all this was a deal reached six years ago to get an orange player.

This bad outcome will be triggered if the Trail Blazers enter the lottery in 2026 and then successfully make the playoffs in 2027. They must avoid this at all costs.

One way to avoid this nightmare is to negotiate with the Bulls. If the Trail Blazers don't make the playoffs this year, they can propose something like this: "Hey, we hold the low lottery pick in 2026. It stands to reason that this pick is more valuable than the non-lottery picks we may give you in the future. Can we make a deal and use this pick to fulfill the obligation to trade Nance that year?" This would settle the trade debt.

But there's a better way: win now. If the Trail Blazers can get out of the lottery this season and have the protected pick transferred to the Bulls next summer, they won't have to worry about 2027. As long as they make sure to hold on to their picks, the 2027 NBA Draft will be stress-free for the Trail Blazers. Even if they had the best record in the league that year, it wouldn't matter if they got the 30th overall pick - they would just swap it with the Bucks and draft in the Bucks' pick..

To summarize: Unless a supplementary agreement is reached with the Bulls to fulfill the obligation to trade Nance, the Trail Blazers have only the following two options:

1. Deliberately lose this year to enter the 2026 lottery, and then continue to deliberately lose to enter the lottery in 2027 to avoid giving the pick to the Bulls and ensure that the draft swap rights with the Bucks do not expire;

2. Go all out to win in the next two years. It is known that the 2026 draft pick will be used to fulfill the trade with the Bulls, thereby preserving the possibility of exchanging draft picks with the Bucks in 2027.

Between deliberately losing for two consecutive years and going all out to win for two consecutive years, the Trail Blazers chose the latter. It's better for team morale, makes better sense logically, and after years of turning a blind eye (more or less) to losing, it's time for a change.

After going through a period of barely concealed failure, it must feel good to now be able to shout "Go all out to win, because this year's draft picks are going to the Bulls anyway. Then continue to go all out to win next year, because we are going to have a better record than the Bucks in 2027. All you have to do is win, win, win!"

Based on this alone, I think that unless serious problems arise, the Trail Blazers will not choose to mess up this season. It doesn't matter if they end up with a mediocre record - because of the obligations of this trade, a mediocre record is better than entering the lottery (unless, of course, the Trail Blazers can get a top-four pick).

The strategic differences that may have existed between the front office, coaching staff and players in past years no longer exist. The Trail Blazers' success benefits everyone. Regardless of the final outcome, it's a strategy that's better suited for this season. I expect they will stay the course.