‘Wild’ 3-Team Blockbuster Proposal Trades Bulls’ DeMar DeRozan, Ex-Top Pick

DeMar DeRozan, Chicago Bulls

Getty DeMar DeRozan #11 of the Chicago Bulls.

The Chicago Bulls’ appetite for extreme makeovers has not been the same since 2021.

They just made their first trade since then during the 2023 NBA Draft, sending second-round picks in 2026 and 2027 to the Washington Wizards for the rights to forward Julian Phillips.

But a team that won six fewer games this past season despite having better health than the previous year needs more than a rookie drafted in the latter stages of the cycle. And there could be a way to get those additional assets and extend their timeline.

[Golden State Warriors star] Draymond Green is an unrestricted free agent, wrote Andy Bailey of Bleacher Report on June 28. “And…[Portland Trail Blazers star Damian] Lillard has an eye for his Western Conference rival…The Portland Trail Blazers don’t figure to have cap space this summer, so Green would have to go in a sign-and-trade.”

This is where the Bulls could come in, as Bailey notes, to “bring it all together” by helping Portland land another star: Lillard’s friend, Bulls forward DeMar DeRozan.

Bulls get:

Jonathan Kuminga
Anfernee Simons
– 2030 1st Rd Pick (via POR)

Blazers get:

– DeMar DeRozan
– Draymond Green (Sign-&-trade, 3yr/$81M)

Warriors get:

Jusuf Nurkic
Shaedon Sharpe
Patrick Williams
– 2026 1st Rd Pick (via POR)

The Bulls would not just be a facilitator in this deal which is easier to break down as separate transactions.


A DeMar DeRozan- Anfernee Simons Swap Extends Window

“Simons is almost 10 years younger than DeRozan,” Bailey notes. “And for a team that finished [30]th in threes per game in 2022-23 (and 16th in three-point percentage), the addition of Simons’ high-volume (and highly accurate) outside shooting has to be intriguing.”

The No. 24 overall pick in the 2018 NBA Draft, Simons averaged career-highs with 21.1 points, 4.1 assists, and 2.6 rebounds this past season. He shot 37.7% from beyond the arc on a career-high 9.1 attempts per game this past season, numbers that would have ranked second and first, respectively, among the Bulls rotation last season.

Simons has canned 39.7% of his triples over the last three seasons while his volume has steadily risen.

DeRozan, 33, is heading into the final year of a three-year, $81.9 million contract.

He is still performing at a high level, earning his second consecutive All-Star appearance this past season. But Simons – who is heading into the second year of a four-year, $100 million pact – could be the smarter play in the long run.


Trading Patrick Williams for Jonathan Kuminga a Tough Sell

“The Williams-for-Kuminga aspect of this deal isn’t quite as easy to explain,” admits Bailey. “But the latter is about a year younger. “And Chicago, which isn’t as close to title contention as the Warriors, can justify the extra development Kuminga may need a bit easier.”

Kuminga, 20, did not take the anticipated step forward this past season. His 9.9 points, 3.4 rebounds, and 1.9 assists per game this past season largely resemble his stat line as a rookie.

He improved his three-point efficiency from 33.6% as a rookie to 37.0% last season.

Williams, 21, averaged 10.2 points, 4.0 rebounds, and 1.2 assists while shooting 46.4% from the floor and 41.5% from beyond the arc in his third NBA season. Following a lost 2021-22 campaign that saw him make just 17 appearances in the regular season, he too failed to take the leap many had him pinned for coming into the season.

But Bulls executive vice president of basketball operations Arturas Karnisovas has been reluctant to include Williams – his first first-round pick as Bulls czar – in trade conversations to this point.

Having been burned by previous decisions, it makes sense Karnisovas could be a bit skittish about venturing back down the path of trading prospects for win-now pieces, though swapping Kuminga for Williams delays having to make a financial commitment by one year.

Still, as Bailey notes, the Bulls signing Nikola Vucevic to a three-year, $60 million contract extension makes a move like this feel less likely, and Karnisovas has pushed continuity for the last two seasons. It will be interesting to see if another shaky start in the 2023-24 season forces their hand.

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