How the Bucks should handle the most important offseason of the Giannis Antetokounmpo era

After a disappointing loss in the Eastern Conference Finals, the Milwaukee Bucks head into NBA free agency with a tricky cap situation. Giannis Antetokounmpo’s contract expires next season, so Milwaukee is facing a crucial summer when it comes to keeping their core intact. The Bucks have to make free-agent decisions on three of their five starters, since Khris Middleton, Malcolm Brogdon, and Brook Lopez will all be free agents.

Milwaukee’s cap situation got a bit easier when they traded Tony Snell and the 30th pick for Jon Leuer last week, saving them some money under the luxury tax to retain the trio. But there’s still a chance Milwaukee must let one (or more) of them walk.

Who is most important? Here is the order in which the Bucks should prioritize their free agents.

Middleton is the second-most important player on this Bucks team. He averaged 18.3 points and six rebounds per game and earned his first all-star appearance last season.

Whenever Antetokounmpo wasn’t on the court and Milwaukee needed a bucket, Middleton was the player with the ball in his hands. He scored 1.09 points per possession on isolations in the regular season, third behind only James Harden and Jimmy Butler among players who ran two or more such plays per game. Middleton averaged a career-high 4.3 assists, showing off his improved playmaking.

The Bucks also use Middleton as their top perimeter defender. He was their first option defending Kawhi Leonard in the Eastern Conference Finals and usually guards the best opposing wing on most nights. With a 6’11 wingspan, Middleton has the size to trouble opposing forwards. He can stay in front of them on drives and uses his length to stymie them when they try to get a shot up.

Middleton showed up in this years playoffs, scoring nearly 17 points while shooting a whopping 43.5 percent from three on six attempts per game. With his shooting range and ability to make a difference on both ends of the court, Middleton has made himself a nice second option next to Antetokounmpo.

Middleton opted out of his $13M player option and will almost certainly command a max contract, so Milwaukee is going to have to splash some cash to keep him. But Milwaukee needs to help Antetokounmpo offensively, and keeping Middleton around will go a long way in achieving that. Both sides are interested in a deal, so from the looks of it, Middleton will be in Milwaukee for the long-term.

Brogdon was one of three Milwaukee point guards that coach Mike Budenholzer played regularly across both backcourt positions. Brogdon’s true shooting and three-point numbers jumped up by four percentage points, and his points per game average went from 13 to 15.6. He cut down on his turnovers and led the league in free throw percentage at 93 percent.

Brogdon gives the Bucks another ball handler to attack closeouts and someone who can stretch the floor with his shooting. He played more shooting guard this season as compared to years prior, so he is versatile. Brogdon also improved defensively under Budenholzer, and though he struggled against bigger guards at times, the Bucks have safety valves for those matchups with the likes of Antetokounmpo, Middleton, and Bledsoe.

Brogdon’s rookie deal is expiring and he’s set to be a restricted free agent. As he starts the prime years of his career at 26, he can be a lead ball handler who can provide outside shooting and switchable defense for contenders and young teams. Milwaukee will have the opportunity to match any contract, but they should be prepared to for the scenario of Brogdon getting a four-year offer sheet that could ranging anywhere from $17-20 million per year, according to ESPN’s Adrian Wojnarowski. Teams like the Chicago Bulls and Dallas Mavericks, to name two, need immediate help at the guard positions.

This will test Milwaukee’s resolve. Can they commit to Brogdon long-term and inch ever closer to the luxury tax line? It’s possible Milwaukee lets him walk if he receives an offer sheet larger than $20 million Absent that, they should try to bring him back given his fit within the Bucks’ scheme.

Lopez had a specific role in Milwaukee’s offense and performed well in it. Lopez would camp out on the three-point line and wait for kick out opportunities when defenses collapsed in on Antetokounmpo and Bledsoe. He shot a career high 36.5 percent from downtown, which gave opposing centers trouble. His shooting ability also vertically stretched out defenses, allowing for players like Antetokounmpo and Middleton to operate with space.

But as important as Lopez was to the Bucks’ offense, they can replace his shooting by signing someone like the Clippers’ JaMychal Green, who can come off the bench as a small-ball center. Last year, Milwaukee signed Lopez to a one-year, $3.3 million deal, meaning they must use cap space they may not have to retain him.

Bringing back Lopez would be nice, but it shouldn’t be prioritized over keeping Middleton or Brogdon.