The Portland Trailblazers have reached a fork in the road and may have to make an important decision very soon. The franchise has been bounced in the first round the last two seasons and in the ultra-competitive Western Conference, they are not good enough to win a championship as currently constructed. Perhaps, new bench boss Chauncey Billups is the answer to the Blazers’ woes after reportedly signing a five-year deal to become the 15th head coach in franchise history, succeeding Terry Stotts. Stotts was reportedly let go after yet another first-round exit and nine years of service. Stotts won 56% of his regular season contests but just 35% of his postseason games, getting past the second round just once during his time in Portland. All Star guard Damian Lillard has been vocal about the issues plaguing the team, revealing his frustrations in an interview with Chris Haynes of Yahoo Sports. “I think that’s the stage we’re at as a team where we all, not just me, not just my teammates, not just our new coaching staff, the front office, everybody in this organization must look in the mirror because we’ve constantly come up short,” said Lillard of the current state of the Blazers. While his loyalty has not come into question before this offseason, the two sides may be heading towards a messy divorce.

Despite some optimism around starting over with the hiring of Billups, the move took place amid significant controversy after Lillard reportedly did not endorse the hiring and was not aware that Billups was accused of sexual assault in 1997, according to Chris Haynes of Yahoo Sports. Making matters more complicated was an interview Lillard gave Jason Quick of The Athletic earlier where he stated he liked Billups and Jason Kidd, who eventually accepted an offer to become the new head coach of the Dallas Mavericks. Portland lost their fair share of goodwill after hiring Billups despite knowing about his past accusations, regardless of whether or not it was proven beyond a reasonable doubt. The team went as far as to shut down questions about the accusation at Billups’ introductory press conference, rubbing many the wrong way.

The Blazers also have to improve significantly on the defensive end, ranking near the bottom of the league in three of the last five seasons. Their defensive woes start with the undersized backcourt of Lillard and CJ McCollum, who probably give up as many points as they score on a nightly basis. While the Blazers have attempted to address their defensive problems by bringing in versatile defenders like Robert Covington and Powell, their team defense still leaves much to be desired. Despite going up against a shorthanded Denver Nuggets team, their inability to defend ultimately cost them the victory in a favourable matchup. While Nurkic is a solid, mobile rim protector who gives his teammates the luxury to gamble when necessary, he lacks defensive awareness. The Bosnian big man is prone to foul trouble, reducing his effectiveness on many nights, not to mention his inability to stay healthy. Moreover, Nurkic is entering the final year of his contract and will look to secure a long-term deal next offseason from the Blazers or elsewhere. Fans certainly hope that the contract year brings out the best in Nurkic for a deep postseason run and will help extend Lillard’s time in Portland.

“I haven’t made any firm decision on what my future will be”

Damian lillard on the rumors surrounding his future with the portland trailblazers

While Lillard has not made a formal trade request yet, rumor has it he could make one in the immediate future, given how stagnant the Blazers have become the last couple of years with not much improvement in sight. Lillard has denied the rumors but stated, “I haven’t made any firm decision on what my future will be. There’s really no need for anyone else to speak for me or report this or report that.” The Blazers technically have time to decide with Lillard under contract for the next four years but if the situation deteriorates even further, it would be wise to test the market. The star guard will turn 35 when his current contract expires and although his game should age well, anything can happen in four years. While the team has not met Lillard’s expectations, there is still reason to believe the star guard is willing to stick around. Jason Quick of The Athletic reported that Lillard had reached out to free agent forward Kelly Oubre Jr. in the hopes of luring him to Portland, but Oubre instead signed with the Charlotte Hornets on a two-year $26 million deal. The takeaway from this is that despite Lillard’s very public frustrations with the team, he is still doing whatever he can to help improve the team to eventually compete for a championship. Part of the reason the Blazers were not able to make any significant moves this offseason aside from re-signing Norman Powell was the lack of financial flexibility with big money tied up to Lillard, CJ McCollum, Robert Covington and Jusuf Nurkic. The Blazers were able to re-sign Powell to a reported 5-year, $90 million contract per ESPN’s Adrian Wojnarowski and a full season with the team should be beneficial for all parties involved. After a relatively slow start in Portland, Powell was able to get back to his normal self during their first-round loss series against the shorthanded Denver Nuggets. Portland has been knocked out of the first round for two straight years now and frustrations are understandably high.

Whether this team as currently constructed without adding another impact player or two and shoring up the defense can win it all is extremely doubtful. For the last couple of months, the most persistent trade rumor in NBA circles was sending McCollum for Philadelphia 76ers guard Ben Simmons after Philly was bounced from the playoffs in the second round. Simmons has been linked to a few teams including Portland and Toronto, but Sixers GM Daryl Morey reportedly has his sights set on McCollum’s backcourt partner instead. According to a report by Marc Stein, Morey still believes that Simmons will fetch an All Star in a potential deal and is interested in Lillard, especially during this tumultuous time in Portland. A more viable option is sending McCollum to the Toronto Raptors in exchange for All Star forward Pascal Siakam, adding another versatile two-way player to the Blazers’ lineup. A deal is not imminent, but preliminary discussions have taken place between the two teams, according to Jake Fischer of Bleacher Report. While Siakam has grown immensely as a scorer, he cannot be relied on to consistently create his own shot—one of McCollum’s strengths. After the departure of franchise icon Kyle Lowry to the Miami Heat, the Raptors may continue to have trouble with their half-court offense—an area where McCollum shines. In addition, the Raptors’ impressive team defense could help mask McCollum’s deficiencies and allow him to focus more on creating scoring opportunities. Perhaps the Blazers would entertain the idea of trading McCollum to allow Norman Powell to play his more natural shooting guard position instead of small forward, shoring up their backcourt defensive in the process. Trading Robert Covington for an upgrade at power forward may also be on the cards given that has been a position of weakness for the last few years after the departure of LaMarcus Aldridge to the San Antonio Spurs back in 2016. Nobody believed that Carmelo Anthony would be the answer as a small-ball power forward either, who has since departed for the Los Angeles Lakers. The Blazers also lost Enes Kanter who signed with the Boston Celtics but added rotation pieces Ben McLemore, Cody Zeller and Tony Snell. Those three are not expected to make a serious impact and given the Blazers’ lack of financial flexibility, it comes as no surprise that they were unable to bolster the roster in a meaningful way. In an ultra-competitive Western Conference, the Blazers are a tier or two below bona fide contenders like the Los Angeles teams, the Utah Jazz, the Phoenix Suns and a presumably healthy Golden State Warriors.

Lillard has carried the team for the last nine years after being drafted sixth overall in 2012 and has become arguably the greatest player in franchise history. Anyone who knows the six-time All Star believes nothing is more important to him than reaching the top of the mountain and winning it all someday. While the Blazers have been a good team for most of his tenure, they were never considered serious contenders for the championship and with their star guard already 31 years of age, the clock is ticking.