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One of the most disappointing teams this past NBA season has to be the Chicago Bulls. After securing a No. 6 seed in the Eastern Conference in the 2021-22 season, and at one point sitting atop the conference, the Bulls completely stumbled and fell in the play-in to the Miami Heat. Injuries certainly played a role, as Lonzo Ball missed the entirety of the season, leaving the Bulls without an adequate replacement in the backcourt for most of the season. To make matters worse, the Bulls don't expect Ball to return next season either, as injuries have hampered his comeback for more than a year now.

Given the lack of success the Bulls experienced last season, and really doing nothing more than just making the playoffs the year prior, one would think that changes are afoot. However, the Bulls just announced that the team is giving big man Nikola Vucevic a three-year, $60 million extension, hinting that perhaps they'll be running it back after all. 

While Vucevic's re-signing isn't all that surprising, given it had been reported earlier in the season that the Bulls were interested in bringing him back, it is a bit of a head-scratcher seeing as the team hasn't experienced much success since acquiring him in a 2021 trade. That's no knock on Vooch, he's been as durable as they come for the Bulls, but he's not without his flaws, primarily his defense and the roller coaster production he provides on offense.

But all of that is moot now that the Bulls have secured Vucevic to a three-year deal. With that finalized, now Chicago turns its attention to free agency, where many roster questions remain. If the Bulls want to make the postseason next year, there will need to be some significant changes to the roster. So with that in mind here are three of the biggest questions facing the Bulls as free agency nears on June 30.

1. Who will be the starting point guard next season?

This is less of a question and more of a need. When Ball didn't return last season the Bulls had a tough time finding an adequate replacement for him in the starting lineup. Despite the best efforts of Ayo Dosunmu, the Bulls had to go and get Patrick Beverley off the buyout market in February, and while he brought some toughness to the team, he comes with limitations as a starter. Given Chicago's lack of cap space, which limits them to using really just the non-taxpayer mid-level exception and the biannual exception this summer, they're going to be limited in the type of players they can target. Bringing back Beverley is always an option, because if nothing else he's a decent option as a facilitator to the stars on the team, and he's always going to give 110% on defense.

Another guy who will be on the open market this summer is Russell Westbrook, who the Bulls recently targeted on the buyout market when he was traded to the Lakers. Westbrook ended up signing with the Clippers, but perhaps the second time is the charm for Chicago. The Clippers have reported interest in bringing Westbrook back, but the Bulls could also make a compelling offer to the former league MVP. He wouldn't have to share ballhandling responsibilities like he did with the Lakers, and if the Bulls upgraded their shooting depth his inefficiency from 3-point range wouldn't be as big of a deal. The pick-and-pop game he could play with Vucevic would be intriguing, and dishing it to guys like Zach LaVine and DeMar DeRozan could make this a potent offense once again. The Bulls won't be the only team interested in signing him, but they were close once before in bringing him to Chicago. 

If it's not Westbrook, then perhaps a nostalgic name may be on Chicago's radar: Derrick Rose. The former league MVP and Bulls fan favorite just had his $15.6 million team option declined by the New York Knicks, making him an unrestricted free agent. A homecoming for Rose would certainly excite fans, however he fell out of New York's rotation last season, raising questions about his level or production as an actual starter. But for the right deal, taking a flier on a 34-year-old Rose to see what he has left in the tank may not be a bad option if the Bulls miss out on other options first.

Whether it's Beverley, Westbrook, Rose or maybe even Dosunmu gets another shot, the Bulls have to nail down who the starting point guard is going to be next season. It was one of their biggest weaknesses last season without Ball, and its one of their biggest needs this offseason. 

2. Will DeRozan or LaVine get traded?

Here's a different route to tweak the roster, whether that be getting a starting-level point guard in return, or adding shooting depth. It's been reported that the Bulls have at least flirted with the idea of trading either LaVine or DeRozan in an effort to upgrade the roster and create some cap flexibility, it's just unclear who would be shipped out. LaVine is likely the more appealing of the two, mainly because of his age (28). He has four years and $178 million remaining on his contract, including a player option for the 2026-27 season, and is set to make over $40 million next season. The matching salary would be hefty heading back to the Bulls, and given LaVine's offensive efficiency and All-Star status, Chicago would net more in a trade for him. But finding that trade partner with the assets Chicago wants is tricky. It's already been reported that LaVine's agency, Klutch Sports, doesn't want him to be traded to the Knicks, though I can't imagine who Chicago would want from that roster aside from Jalen Brunson, who is surely untouchable for New York. 

Trading LaVine would be a huge shift in Chicago's plans, especially since he just signed that max contract last July. But if the right offer came along, perhaps the Bulls consider it. If Chicago didn't want to make such a drastic change, perhaps trading DeRozan would be the more palatable move. The 33 year old is on a $28.6 million expiring deal next season, making his contract more enticing to contending teams on a budget. The return wouldn't be as robust as one the Bulls would get for LaVine, but if Chicago had qualms about re-signing DeRozan next summer, trading him now instead of losing him for nothing would be the smart move. DeRozan has quieted critics who questioned Chicago trading for him back in 2021, but the Bulls have limited options to improve the roster going forward. So if trading DeRozan would net them a proven shooter or a quality starting guard then Chicago has to explore that route. 

3. How do you improve the shooting depth?

The Bulls ranked last in the league in 3-point attempts per game, and ranked 16th in efficiency last season, and it was evident when you watched them play that serious upgrades are needed. LaVine is perhaps the only surefire 3-point threat on the roster, but he alone can't be the only one you go to when you need a shot from deep. There were too many times last season where the Bulls would get into a significant deficit because they can't keep up with other teams making them at a high clip. If the Bulls decide not to trade either of LaVine or DeRozan, then adding shooting depth in free agency is the route to go. There's going to be a handful of options on the table when free agency starts, it's just a matter of the Bulls competing with other teams to sign those guys.

Guys like Max Strus and Gabe Vincent will likely be in high demand by their current team -- the Miami Heat -- as well as other teams around the league. But those are two targets that would be ideal fits on this roster. While Strus struggled in the NBA Finals to connect from deep, he along with Vincent were primary reasons why Miami had such a deep postseason run. They don't need the ball in their hands, which is ideal when you already have DeRozan and LaVine on the roster, and have proven to be reliable 3-point shooters. There's also someone like Seth Curry, who is an unrestricted free agent this summer and is a career 43.5% 3-point shooter. Or perhaps there's a trade out there to be made for the Bulls that nets them a valuable shooter without giving up too much. 

However the Bulls accomplish it, improving their shooting depth is an important step in upgrading this roster. The good news is there should be plenty of options for them to consider, it's just a matter of if the money lines up. If Chicago manages to get someone like Curry or another shooter, and either re-signs Beverley or gets a starter quality point guard in place of Ball then the Bulls should be in better shape to compete for a playoff spot next season.