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How Many Wins Keep Lillard Happy At The Deadline?

While Damian Lillard has professed his love for Portland, what kind of deadline win-loss record will prompt him to look at alternatives.

Denver Nuggets v Portland Trail Blazers - Game Six Photo by Steph Chambers/Getty Images

I just want to preface this by saying no one but Damian Lillard knows what Damian Lillard is thinking.

The Portland Trail Blazers are about to gear up for another season. And unlike the previous nine, the long-term future of their All-NBA point guard is tentative, at best. Yes, I know Damian Lillard posted his love for the city of Portland on Instagram last week, and that’s great. But even the most ardent fans need to understand that he’s not going to serve out the length of his contract if this team remains middle of the road.

The trade deadline is a landmark day — or week — on the NBA calendar, often giving fans hope of a better player, picks and/or a new outlook for the remainder of the season. But the deadline might also be a catalyst for star players to acknowledge their time with a particular franchise might be done.

Just to be clear and please put down your pitchforks — go on, put them down; I’m not suggesting the 31-year-old will publicly ask out at the deadline. He won’t; it’s not his style. All I’m saying is that the deadline might be a poignant point for the likely seven-time All-Star to seriously assess his future.

Earlier this offseason, True Hoop’s Henry Abbott reported that Lillard was on the verge of demanding a trade from Portland, further fuelling speculation that the point guard might be looking elsewhere.

Lillard also told reporters last season’s Blazers roster wasn’t good enough to contend for a title. However, Yahoo Sports’ Chris Haynes reported last month that Lillard was prepared to give the Blazers and rookie Head Coach Chauncey Billups a chance.

The question then is: how long before that chance is gone? Most NBA pundits have suggested that while the regular season is important, it’ll be the playoffs that will ultimately illuminate Lillard’s true feelings about this team.

But if the regular season starts poorly and continues down that road, how fast will Lillard call President of Basketball Operations Neil Olshey and ask for a new chapter at the end of the Blazers’ 2021-22 campaign?

Before we go any further, I just want to say: I don’t want this. If it was up to me, Lillard would be a career Blazer, but unfortunately we live in the real world, where competing goals such as championships and Finals appearances play a very important role.

This season’s deadline

Going on previous years, the 2022 trade deadline — yet to be confirmed — is likely to land on the Thursday a week before the All-Star Break. This year’s All-Star game will take place on Sunday, February 20th, so let’s work with a deadline date of Thursday, February 10th.

Consequently, the Blazers have 55 games before the deadline with the last game on February 9th at home against the Orlando Magic. The team also hosts the Los Angeles Lakers the night of the potential deadline at the Moda Center.

The Blazers schedule and projected wins

In order for the Blazers to remain above .500 by the deadline, they’d need to collect 28 wins.

Pre-deadline Portland has 30 home games and obviously 25 road games with nine back to backs and 29 hitouts against teams who were above .500 last season. Now, being conservative and assuming the Blazers aren’t battling serious, long-term injuries this season, 28 wins should be more than achievable.

One positive will be the increase of fans in the Moda Center, a formidable arena that can intimidate even the best teams in the league.

Other factors

While incredibly unfortunate, if CJ McCollum, Jusuf Nurkic, Robert Covington, Norman Powell and Larry Nance Jr. all go down with long-term injuries in the early part of the season, it’ll be interesting to see how Lillard handles his future.

For someone who unabashedly wants to win a championship in Portland, it’d be odd to ask out if injuries were reason for the team’s failures.

Lillard’s legitimate gripe with this team is that it’s not constructed in a way that allows it to contend. And so if injuries were the stumbling block this season, he probably doesn’t have firm enough ground to complain.

Secondly, while unlikely, Lillard could start the season flat relative to his own lofty standards. There is arguably no more self-aware player in the NBA, and if Lillard is slow out of the blocks through those first 55 games, it’s unlikely he will ask out knowing he wasn’t living up to his end of the bargain.

Lillard is one of the NBA’s smartest players in reading and manipulating his image to meet public expectations and if he asks out while he’s off or the team is decimated by injury, it’s not going to look good.

What record would keep Lillard happy?

I believe there are various levels of unhappiness Lillard is willing to endure in Portland next season. I’m going to go out on a limb and suggest that if the Blazers hold a 24-31 record at the deadline with everyone fit, private talks may be had with Olshey about finding Lillard a new home. But I’ll clarify that by suggesting that anything less than .500 could also prompt discontent.

Lillard has made his clearest statement yet about the quality of a Blazers squad and with this roster potentially as close to the standard it was during the team’s 2019 Western Conference Finals run, a sub .500 record would not stand. Again, we’re not suggesting Lillard publicly asks out at this point: this is purely the trigger for the star point guard to quietly request a move at season’s end.

The moral to this story is that the Blazers need to get off to a good start regardless of the fact that they have a rookie coach still finding his feet in the big seat.

A strong start would not only achieve the obvious team success but also quell some of the noise, drama and dialogue surrounding Lillard’s future with the franchise. We know the media and the broader Twitterverse will be there every time the Blazers lose games. But the fewer losses, the less scrutiny this team receives, which relieves pressure on every player, including Lillard.