Damian Lillard has only missed the playoffs one single time in his career. That was his rookie season. Despite that, over half of those playoff appearances have ended in first round exits, and the Portland Trail Blazers have yet to make it past the conference finals. 

Lillard is beloved in the Pacific NorthWest. He’s on billboards, in commercials, takes part in charity events, and seems to genuinely love being part of the community. A superstar on the court and a local hero off of it, Lillard would never demand a trade from this city that’s come to embrace him so much, right?

Well, not so fast. The 2020-21 Trail Blazers, once again, have been eliminated in the first round of the NBA Playoffs. This time, however, it feels… different. Lillard carried the team to a Game 5 comeback, scoring 55 points on just 24 shots, notching 10 assists, and setting an NBA playoff record with 12 made 3-pointers.

In the second and final overtime, Lillard’s teammates could not help him to the finish line. Poor defense, missed shots, turnovers, and bad fouls plagued the final minutes of the game, and Lillard watched his historic night turn sour. This is a huge disappointment for a Blazers team that made key upgrades in the offseason with the hopes that this could be the year to finally contend with the powerhouses of the Western Conference.

It wasn’t, and one must ask themselves when too much is just too much. Year after year, the Trail Blazers attempt to take the next step by acquiring talented veterans and making trades for role players. Coach Terry Stotts is no doubt on the hot seat, and it would not come as a surprise if he is looking for a job in the coming weeks.

Why Would Damian Lillard Leave Portland?

Lillard, to his credit, has always been a loyal franchise player. But watching what Kyrie, KD, and James Harden did in Brooklyn, what Kawhi and Paul George did in LA, and what Lebron and AD did for the Lakers, Lillard might be thinking to himself right now that the only way to win a ring in the modern NBA is to pair up with one or two other true stars. 

The situation is reminiscent of Russell Westbrook’s final years in Oklahoma City. Similarly loyal to the franchise and the city despite years of disappointment in the playoffs, Westbrook didn’t demand to leave the team on bad terms. Instead, the team was looking towards a total rebuild, and they made sure to send Russ to a destination he liked for a very good return. 

Damian Lillard might want to push the Trail Blazers in a similar direction. And if that were to happen, every team in the NBA would be salivating at the thought of acquiring a 30-year old phenom who only seems to be getting better. One such team, a team that’s on the cusp of contending, a team that desperately needs a point guard, and a team that could be an instant playoff contender with the addition of another star… is the Chicago Bulls. 

Look, before you get upset and poke holes in everything you’ve read thus far, remember that you’re reading this article on a website called arturasfanclub.com. What more did you expect? Of course we’re mocking Lillard to the Bulls. That’s what we do here. 

What Moves Do The Bulls Need To Make?

In order to acquire Damian Lillard, the Bulls have a few key moves to make. They would need to stretch and waive the contracts of Al-Farouq Aminu and Tomas Satoransky (or find a way to get Portland to accept them in a deal, good luck), renounce the rights to Lauri Markkanen and Ryan Arcidiacono, and likely trade away some package consisting of Coby White and Patrick Williams. 

A word on Patrick Williams: trading him so soon in his career would be hugely bittersweet. Acquiring Dame is absolutely worth it, but I can understand why some Bulls fans would be adverse to this idea. Just remember that Zach Lavine and Nikola Vucevic are not getting any younger. Acquiring Dame is a win-now move that would lead to talented veterans taking minimum deals to sign with the Bulls and their new Big Three. 

The Bulls are light on picks right now, and due to the Stepien Rule, they cannot trade first rounders in 2022 or 2024. That presents a unique challenge that might require a third team to get involved in order to truly make this deal worth it to Portland. If you’re Arturas Karnisovas, you do whatever it takes to acquire Damian Lillard. That said, there is still a 20.3% chance that the Bulls retain their 2021 first round pick as long as it lands in the top four. A top four pick, plus the players already mentioned, might get this trade done on their own…

Convincing Damian Lillard To Choose Chicago

Part of the process of acquiring Lillard is convincing him that Chicago is the right destination, as surely many teams will be clamoring to get him, and the Trail Blazers have a vested interest in keeping him happy throughout this process to avoid a Harden/Anthony Davis situation. Moving to the third largest market in the NBA would immediately skyrocket Lillard’s already huge image, and provide numerous sponsorship and brand opportunities.

Not only that, but restoring glory to the Bulls franchise is something that many players could only dream of accomplishing. You see, there was this bald fellow in the 1990s who played for the Bulls and was moderately successful. Winning the next title in Chicago would firmly place your name next to his in history books forever.

Aside from the prestige of the franchise and the amazing city they play in, the Bulls have a lot going for them right now. Billy Donovan is a huge upgrade over Terry Stotts, and Zach Lavine has cemented himself as one of the best scorers on the face of planet Earth. Nikola Vucevic’s presence creates scoring opportunities and defensive mismatches. Lillard is, essentially, a perfect fit (so as long as the Bulls can find some defense elsewhere).

Bulls Salary Cap Situation

In the scenario presented above, the Bulls roster post-trade would look something like this:

• Damian Lillard – $39 mil*
• Zach Lavine – $19.5 mil
• Troy Brown Jr – $3 mil
• Thaddeus Young – $13.5 mil
• Nikola Vucevic – $26 mil
• TOTAL SALARY: $101 mil (CAP: $112 mil, LUXURY TAX: $136.6 mil)

*this number will increase by $3 mil every year

There’s still much work to be done here, but as far as starting fives go, this would easily be the best the Bulls have put together since the Rose/Noah/Butler years, and possibly the best of Lillard’s career, as well. In order to fill out the rest of the roster, here are a few moves the team could make:

• Re-sign Daniel Theis using his bird rights to go over the salary cap 
• Execute a sign and trade with Lauri Markkanen to acquire role players from a team such as the Dallas Mavericks or the San Antonio Spurs 
• Use the mid-level exception to acquire a talented reserve (think of names like TJ McConnell, Spencer Dinwiddie, Derrick Rose, Serge Ibaka, Bobby Portis, etc)
• Attract talented veterans on minimum deals who want to win a ring

After working his magic, Arturas Karnisovas could come out on the other side of this with a true, honest-to-God NBA Finals contender. Not a playoff contender. Not a conference finals contender. A team that is actually built to win the whole damn thing. 

There are a lot of what-ifs that would need to fall in the Bulls’ favor for any of this to come to fruition. In AK’s short time with the team so far, many of those dominoes have actually fallen their way. 

From lucking into a top four pick, to the timing of Billy Donovan’s dismissal from OKC, to Nikola Vucevic becoming available in trade talks, Arturas Karnisovas has shown not only an aggressive, can-do attitude, but he’s also just been kinda lucky. 

Maybe the luck continues, and maybe he makes an even bigger blockbuster trade than the last one. So far, he’s given us zero reason to doubt him.

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