The Milwaukee Bucks face a complex offseason that will challenge their front office to balance short-term winning versus long-term team-building.

They prematurely bowed out of the playoffs in embarrassing fashion, losing to the eighth-seeded Miami Heat in just five games in the first round. That’s an unacceptable result for a team built to win now. It’s also led to a sense of desperation, as Jon Horst is left, once again, needing to prove their commitment to Giannis Antetokounmpo.

Milwaukee was already rumored to be involved in the Bradley Beal sweepstakes, but fell short to the Phoenix Suns. That could be the start of an offseason motivation to improve the team at the top of the depth chart.

That’s where the most significant challenge arises. Milwaukee has minimal tools to improve their team outside of retaining the same squad that fell woefully short in the postseason. They must also balance the line of the second apron—a figure in the new CBA that further limits what assets a team can use once they cross it. It implements restrictions on mid-level exceptions, trades and other penalties.

To better understand where the Bucks are, here's your handbook to everything Bucks this offseason.

The 2023 NBA Draft is nearly upon us. It’s been tranquil in Milwaukee, however, as they only hold the 58th selection (the last pick in the second round, but two other teams forfeited second-rounders due to league violations).

The Bucks are reportedly interested in acquiring a late first-round pick or early second in this year’s draft, with their eyes set on an older wing who could make an immediate impact. I’m unclear how they would obtain such a pick, but Horst always does his due diligence. For now, these are the only draft picks they have available:

Khris Middleton: Middleton has a $40.4 million player option he needs to decide on by June 21. He’s coming off a down season in which he battled injuries for most of it and was never able to showcase his skills at full strength. That hurts his immediate value, but Milwaukee is extremely limited in their path to acquire talent anywhere close to Middleton’s.

If Middleton opts out, he can’t re-sign a deal with the Bucks that is worth less than his player option until after free agency begins. That’s an important detail to understand about how the timing of this all works. If he declines his option, the max contract Milwaukee can offer him before free agency is for five years and $272 million. If he accepts, they could ink him to an extension of up to four years and $204 million.

Jevon Carter: Carter's $2.2 million player option must be decided on by June 29, giving him more time than Middleton. Carter earned a full-time role with the Bucks last year and is likely in line for a raise from someone. If he opts out, the Bucks will have early bird rights on him, allowing them to re-sign him to a deal for at least two years and worth up to a first-year salary of $11.3 million.

Lopez is the big (no pun intended) free agent to monitor on this list. He’s essential to what they accomplished on both ends of the court and appears to have a lot left in the tank.

Due to how the new CBA works, it all becomes a math game for Milwaukee. The second apron sits at $179.5 million. If Middleton and Carter opt out, the Bucks would have about $49 million to re-sign Middleton and Lopez, $5 million for the taxpayer mid-level exception and then veteran minimums to fill out the rest of their roster. As Bucks’ legend Frank Madden points out, that puts them in a hard-cap situation where they can’t cross the second apron threshold at any point next season.

Under Contract: 8 players

Active Roster Cap: $157.9 million (includes Middleton’s $40.4 million player option and Carter’s $2.2 million player option)

Luxury Tax Space: $4.1 million

Apron Space: $5.9 million

Second Apron Space: $16.4 million

The Bucks will potentially have the ability to use their taxpayer mid-level exception this season to pay a free agent (theirs or someone else's) $5 million next year. This tool will only be available to the Bucks if they hard-cap themselves under the second apron at $179.5 million. If they go over that at any point next season, they will be unable to use it.