The Chicago Bulls are a great story this season. They’ve transformed from a lottery joke to a middle-of-the-pack playoff squad in the crowded Eastern Conference. Not a bad one-year swing.
- The Chicago Bulls Become The Best Offensive Squad In The League
- The Portland Trail Blazers Start Over
- Our Deal Makes Sense For Both Sides
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Still, Windy City fans who dream of celebrating a 2021-22 championship need to take a long swig of reality. The Bulls have a 21-21 record versus teams over .500, and after going 3-7 over their last ten games, find themselves in real danger of slipping out of one of the coveted top-6 postseason spots in the Eastern Conference to the streaking Toronto Raptors.
The Bulls’ recent beat down to the Suns is a perfect example of their deficiencies. Phoenix’s number three defense gave Chicago fits. Mikal Bridges held MVP candidate DeMar DeRozan to 19 points on 6-14 from the field. At the same time, Devin Booker, Cameron Payne, and Elfrid Payton hounded Zach LaVine into a putrid 1 for 7 shooting night and made the typically cerebral rookie Ayo Dosunmu look like a scared puppy searching for his mom. Chicago had no answer for Devin Booker and DeAndre Ayton on the less glamorous side of the ball, and even role players, Mikal Bridges and Jae Crowder seemed to score whenever they wanted to. The Suns completely outplayed the Bulls, running them over by 27 points. AND Phoenix did it all without MVP candidate, Chris Paul.
It’s hard to imagine Chicago putting up enough points against the Bucks’ long-armed and athletic defense to win a seven-game playoff series. The same goes for the Bulls against the Heat and Celtics, two squads that also boast excellent defensive units.
Over on the west coast, the Portland Trail Blazers were the most active team at the 2022 trade deadline, consummating three deals in February.
First, they sent Norman Powell and Robert Covington to the Clippers in exchange for Eric Bledsoe, Justice Winslow, Keon Johnson, and a second-round pick.
Then they traded CJ McCollum, Larry Nance Jr., and Tony Snell to New Orleans for Josh Hart, Nickeil Alexander-Walker, Tomas Satoransky, Didi Louzada, a protected 2022 first-round pick, and two future second-round picks.
Finally, they jumped into a three-team trade that sent out recently acquired Nickeil Alexander-Walker and Tomas Satoransky to the Utah Jazz for injured Joe Ingles, who’s set to become an unrestricted free agent after the season.
Trade Summary: The Trail Blazers sent out most of their starting lineup (McCollum, Powell, and Covington) for an assortment of bench players (outside of Josh Hart, he’s a legitimate NBA starter), half of whom could be out of the league in the next two seasons.
Portland wanted to clear their cap sheet for a run at another max player to pair with Damian Lillard, but it’s slim pickings this offseason. James Harden, Bradley Beal, and Kyrie Irving all have player options for next season but have shown zero interest in heading over to Oregon. Zach LaVine will be the best available unrestricted free agent hitting the market over the summer, but he’s given every indication he’s coming back to Chicago on a max deal. Perhaps the Trail Blazers can land some combination of Deandre Ayton, Bobby Portis, T. J. Warren, and Joe Ingles. Suppose they have the best possible (realistic) offseason by signing Deandre Ayton and Joe Ingles. Will a starting lineup of D. Lillard, A. Simons, J. Hart, J. Ingles, and D. Ayton contend for a title?
No.
The Trail Blazers’ best imaginable offseason will top them out as second-round playoff fodder for the Suns, Mavs, Warriors., or a healthy Clippers team
The Bulls are one superstar away from becoming a genuine title contender, and the Trail Blazers, with Damian Lillard, forecast as a fringe playoff team.
Chicago and Portland should consummate a deal this summer, helping each squad get where they need to go:
Chicago Bulls Receive: Damian Lillard
Portland Trail Blazers Receive: Lonzo Ball, Alex Caruso, Ayo Dosunmu, Coby White, Patrick Williams, 2023 first-round pick, 2024 second-round pick
Below we’ll outline the benefits of our blockbuster trade for the Bulls and Trail Blazers.
The Chicago Bulls Become The Best Offensive Squad In The League

Let’s begin by addressing any concerns about Damian Lillard’s ability to rain down offensive death after his poor 2021-22 showing.
It’s true Lillard was an inefficient mess throughout his 29 games this season. He shot 32.4% from deep and 40.2% overall from the field. He was playing through an abdominal issue before he shut it down and went under the knife to ensure he’s 100% for the beginning of next season.
Last season Lillard was a top-10 player, averaging 28.8 PPG while dishing out 7.5 APG. He also shot 39.1% from deep and hit a handful of game-clinching buzzer-beaters for the Blazers. Then in the playoffs, he averaged 34.3 PPG on a 44.9% clip from beyond the arc before his over-matched Portland squad succumbed to the Nuggets in the first round.
In 2019 – 20, Damian Lillard was an MVP candidate. He poured in 30.0 PPG, 8.0 APG, on 40.1% from deep, as he averaged 7.7 fourth-quarter points per game, good for 5th in the league. He played his usual brand of excellent basketball in the playoffs, but his Trail Blazers team was overwhelmed by the physicality of the eventual champion Lakers in the first round of the playoffs.
Damian Lillard, 31, is firmly in the middle of his prime, and there’s no reason to think his performance this year was anything more than an injury-plagued outlier.
Let’s get to the meat of this deal.
Bulls fans will undoubtedly put their hands on their hips, eyebrows furrowed, as they scream out, “We can’t give away five players and future draft compensation for one player, even if he’s top-10 in the league. It’s not worth it!”
Really?
It would be a tsunami-sized shock if the Bulls take down either the Bucks, Heat, 76ers, or Celtics in the playoffs and make it to the Eastern Conference finals. AND this might be as good as it gets for Chicago.
DeMar DeRozan morphed from a non-All-Star over the past three seasons, averaging roughly 21.0 points per game on a 22.0% mark from deep in San Antonio to an MVP candidate this year. We’ve seen players level up in their 20s, but we’ve never witnessed someone jump as DeRozan has at age 32.
DeMar DeRozan has dominated the league on an array of off-the-dribble mid-range jumpers like an in-his-prime Kobe Bryant. DeRozan is taking 20.1 shots per game, and 12.1 are tightly contested (closest defender is within 2 to 4 feet) jumpers, which is ridiculous. Still, he’s somehow hitting a 51.2% clip on those tightly contested shots, which is nearly unheard of.
When you add up DeRozan’s age 32 ascension with how he’s produced his buckets, it’s fair to ask if DeRozan’s 2021-22 season is a one-off. He could easily slip back to his San Antonio production next year, averaging 21.0 PPG. And if he does slip, the Bulls, who’ve relied on DeRozan’s one-on-one heroics to rack up wins this year, will be a play-in team in 2022-23.
Damian Lillard and his offensive mastery would be a hedge against any DeRozan regression next season. The Bulls would feature the best shooting backcourt in the Eastern Conference, with Lillard and LaVine forming an off-the-dribble three-point shooting nightmare for opposing squads. Together they would open up numerous wide-open mid-range looks for DeRozan, who would drain his uncontested looks with a smile on his face after shooting (I’m going to mention it again) 60% of his attempts with a defender within 2 to 4 feet of him in 2021-22. Nikola Vucevic has a clean inside game and would feast on the open bunnies at the rim the Bulls Big-3 would create for him.
The 2022-23 Bulls starting lineup would send opposing squads into convulsions:
PG: Damian Lillard
SG: Zach LaVine
SF: DeMar DeRozan
PF: Tristan Thompson
C: Nikola Vucevic
Chicago management would have to scour the free-agent market for a few solid two-way veterans looking for a title, and perhaps the Bulls would struggle to get stops. Still, this is a championship-level squad that would rain in so many buckets nightly that they wouldn’t need to feature a top-10 defense.
The Portland Trail Blazers Start Over

After the Trail Blazers gutted their roster at the trade deadline, they guaranteed a trip into NBA no-man’s-land if they don’t finish their in-season rebuild and trade Damian Lillard. If Portland management keeps their superstar point guard, at best, they’re a middle-tier playoff team with no hope of making a title run in 2022-23 and beyond. At worst, they’ll miss the playoffs but win enough games to miss out on a top-5 pick and a chance at a future star. Either way, they ensure they won’t hang a banner this decade.
Portland needs to suck up and pull the last piece out the bottom of the Jenga set, collapsing the roster to rebuild over the next couple of seasons and give their fans real hope of building a two-way roster with genuine championship aspirations.
In our trade, the Bulls receive four solid guards in Lonzo Ball, Alex Caruso, Ayo Dosunmu, Coby White, along with young and athletic Patrick Williams at the power forward position.
The Trail Blazers 2022-23 roster would headline four guards from the Bulls, plus incumbents Anfernee Simons, Josh Hart, and Keon Johnson, all fighting for playing time in the backcourt. Portland would have to go small, featuring one of their guards at the small forward position in the starting lineup and another off the bench. The Trail Blazers would also be thin as a dumpling wrapper in the frontcourt, and they’d be starless.
Good!!!!!.
The Trail Blazers would fall to the bottom of the Western Conference standings, which is the point. They’d bottom out for the next couple of seasons, giving them an excellent chance at landing a superstar in the draft while their young assets would have an opportunity to work out their kinks on the court.
The Trail Blazers would have a legitimate course of action. With luck (a title always takes a significant amount of luck), Ayo Dosunmu would grow into a top-40 player, forming synergy with Lonzo Ball in the starting unit. Alex Caruso and Josh Hart would become the best bench backcourt in the league, overwhelming teams with their two-way aggression. And Portland would sign one (or even two) frontcourt difference makers over the next couple of offseasons.
The Trail Blazers would surround their top draft picks with an excellent two-way roster, and they’d be ready to compete for something real instead of chasing the second round of the playoffs with Lillard in the fold.
Our Deal Makes Sense For Both Sides
The Bulls are a solid 2021-22 squad, but they’re clearly one piece away from competing with the big boys in the Eastern Conference. Damian Lillard, united with DeMar DeRozan and Zach LaVine, would give Chicago the best Big-3 in the league. They’d have a real shot at climbing the mountain next season.
The Trail Blazers have two options: Keep Damian Lillard and chase second-round playoff glory for the next few seasons before crashing into the lottery, or trade their superstar for a handful of excellent young players and a chance to build a future title contender. The choice is obvious. In the NBA, it’s championship or bust.