DeMar DeRozan at a crossroad with the Chicago Bulls as he enters free agency after another season without a playoff run

DeMar DeRozan is tired of watching the NBA playoffs on TV.

More specifically, the first round of the playoffs. Hell, even the second round. He’s sick of being stuck on the sideline for the most important basketball being played every year. And after his fifth straight season without a meaningful playoff series came crashing to a halt Friday night with a 112-91 loss to the Heat in Miami, the frustration was hard to hide.

“At the end of the day, I hate losing,” DeRozan said. “It really hits you after the season, when you look up, the last seconds run off, you know you don’t have another game.”

As DeRozan enters free agency this summer, he faces a crucial question: Does he hate losing more than he loves the consistent comfort of Chicago?

The Bulls never have been true playoff contenders in DeRozan’s three seasons in Chicago. With the injured Lonzo Ball two years removed from the court and Zach LaVine still posing a conundrum after making a midseason trade request, the team is likely on poor footing to make a postseason run in the near future.

And timing is everything when it comes to DeRozan. The 34-year-old veteran tends to brush off references to his age. But after Friday’s loss, it was clear the passage of time was carrying a heavier weight.

“The next time I play a game, it’ll be my 16th season,” DeRozan said. “You realize the window closes for you personally. I ain’t trying to play 25 years or nothing like that. You just want to have the opportunity to give everything great in you opportunity.

“My stance on wanting to be here is still the same, but I just want to win more than anything. Just have the opportunity to win and not got to go home and see the first round of the playoffs, second round of the playoffs. It’s frustrating.”

DeRozan entered the season with a consistent message: He wanted to stay in Chicago. At least publicly, that sentiment never wavered. Each time he faced questions about his mindset as a free agent, DeRozan reiterated that he loved Chicago, believed in the Bulls organization and wanted to come to a deal this summer.

After shootaround Friday morning — just hours before the Bulls season ended — DeRozan cited the growth of Ayo Dosunmu and Coby White as a key factor in his eagerness to return. He believes there is a young foundation sturdy enough to build a successful team.

“There’s so much to it, but all you need is a competitive core,” DeRozan said. “When you have that, you can build off that in so many ways. Guys like that make it easier to want to be a part of something. I love going to war with those guys and I want to reap the fruits of everything that comes with being successful with those guys because I know how hard they work and how hard they want it.”

Friday’s loss might have cracked that optimism. DeRozan didn’t outright express a desire to leave the Bulls. But for the first time in three years, his language was tinged with a resignation that Chicago might not be a viable route toward playoff success, nudging open the door to a potential future with a different team.

This is a critical point for both DeRozan and the Bulls — one that could define the success of both parties for a half-decade.

There’s no denying DeRozan’s impact during his tenure with the Bulls, buoying the team’s scoring and offense. DeRozan led the league in minutes played this season, averaging fewer than 11 minutes on the bench per game, a feat only 13 players age 34 or older have accomplished.

DeRozan’s hard-nosed mentality on the court paired crucially with his affectionate mentorship off it, expediting the progress of White and Dosunmu. And this presence is why DeRozan’s teammates are eager to see the veteran cornerstone return next season — no matter the cost.

“It would mean everything,” White said. “Whatever he want, I think he should get paid — whatever he wants. It’ll be important for us to have him back and me personally, I really want him back. So hopefully they can get everything done and he can be back in a Chicago Bulls uniform.”

But sometimes, the timing just isn’t right — and that seems to be the case for the Bulls and DeRozan.

If the six-time All-Star asks for the veteran maximum available to him, the Bulls would have to lock into a four-year, $179.4 million contract that would likely push them into the luxury tax. Chairman Jerry Reinsdorf has claimed he’s willing to enter the luxury tax, but only to build a roster that could be a deep playoff contender — which has never been true with DeRozan on the roster.

The Bulls could clear up cap space by moving Zach LaVine over the summer, but investing this heavily into the longevity of a soon-to-be 35-year-old forward works in direct opposition to the tactic of building around a young core. And if digging into a long-term deal with DeRozan wouldn’t pay off, it could waste the final years of affordable contracts for White and Dosunmu, both of whom hit free agency in 2026.

During his exit interview Saturday, executive vice president of basketball operations Artūras Karnišovas acknowledged the necessity for change to find success. But he also expressed continued confidence in DeRozan’s ability to make an impact in Chicago.

“DeMar’s been great for us for three years,” Karnišovas said. “He’s been invested in the city of Chicago and has been really great to our young guys. Both sides are interested in continuing, so we’ll see what happens in free agency.”

Even through the fog of frustration on Friday, DeRozan made clear he doesn’t want to make any impulse decisions about his next steps.

And that left little hints of how he will approach the offseason and his free agency.

“It’s just going to be a long summer for me,” DeRozan said. “It’s kind of like crawling up that hill. You get knocked back down, you take that look up the mountain and you say, ‘Damn, I gotta do it all over again, gotta figure it out.’ ”