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It seemed fitting that Damian Lillard sat courtside Monday night at the United Center to watch his close friend DeMar DeRozan close out his longtime former team in the Portland Trail Blazers.
"It was cool," DeRozan said following the Chicago Bulls' 110-107 victory. "I woke up from my nap and he texted me. And I was like, 'Alright, I got you with my tickets.' That's one of my good friends outside of basketball. To see him come out here and support me and watch his old team was cool."
Lillard and DeRozan are not only close, but they share an agency. The same agency that helped find Lillard a solid new home in the Milwaukee Bucks when his preferred destination of the Miami Heat didn't pan out after Lillard finally asked to be traded from Portland.
The same agency that helped DeRozan land a three-year, $81.9 million contract with the Bulls in a sign-and-trade transaction from the San Antonio Spurs when DeRozan's preferred destination of the Los Angeles Lakers failed to materialize in 2021 free agency.
DeRozan has outplayed that contract. In his three seasons in Chicago, he has made two All-Star teams, remained one of the NBA's most deadly closers and helped the growth of young players like Coby White with his steady leadership and consistent personality.
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DeRozan is getting more and more indispensable---and seemingly expensive---by the game, particularly given management's publicly stated stance that it wants to remain competitive. In season No. 15, he leads the NBA in total minutes, logging 40 more on Monday night, a game the Bulls likely hoped he could play less given Portland's mere 19 victories.
He again made several big plays late, including feeding Nikola Vučević for a crucial basket when the Trail Blazers double-teamed him. He finished with 28 points, six assists and five rebounds.
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"You know what's crazy is I learned a technique years ago when it comes to swimming and boxing to be able to stay focused no matter how tired you get," DeRozan said. "Never panic when you're in the water. And never let you feel fatigue when you're boxing. That's two training methods outside of basketball that I take serious every summer. And I've been doing that for years.
"A lot of times, late-game moments is where I'm able to control a lot of my exertion. I know how to channel it somewhere else and think clearly."
DeRozan always downplays the business side of basketball. But he's headed to unrestricted free agency in July unless the Bulls sign him to an extension first. Executive vice president Artūras Karnišovas has said publicly multiple times that he wants to retain DeRozan.
But multiple outlets, including NBC Sports Chicago, reported earlier this season that the two sides haven't come close to finding common ground yet.
Last offseason, the Bulls re-signed Vučević to a three-year, $60 million deal before he hit unrestricted free agency. Critics of the deal maintained the Bulls bid against themselves, that no team with salary-cap space would've offered as much.
And while there is speculation that DeRozan would be in a similar situation, a league source insists that he will draw suitors if he gets to unrestricted free agency. The needle the Bulls must thread if they want to re-sign DeRozan and Patrick Williams and avoid paying the luxury tax will be a tight one, particularly if Zach LaVine and Lonzo Ball remain on next season's payroll.
But the thinking that the Bulls may be able to re-sign DeRozan for a pay cut is dwindling by the game. His impact on the Bulls' 29-21 record since a miserable 5-14 start to the season is undeniable.
When DeRozan spoke in Memphis at the morning shootaround on Feb. 8, just hours before the NBA trade deadline, he certainly sounded like a player who wanted to re-sign in Chicago---and one who knew the Bulls can't afford to lose him for nothing.
But just like some never thought Lillard would ask out of Portland, there are no guarantees until a contract is signed. And DeRozan's play on the court and poise off it is deserving of a big one.
"I just love hooping," DeRozan said. "I love playing the game, no matter how many minutes it is. I just love being out there."
