After a painful collapse against the Toronto Raptors in the Eastern Conference Finals – both in the series and the second half of Game 6 – the Milwaukee Bucks are suddenly staring down the franchise’s most important offseason since it traded Kareem Abdul-Jabbar in 1975. Here are nine questions to help sort through the upcoming hoops madness.

When does NBA free agency begin?

12:01 a.m. ET on July 1. Of course, while free agency doesn’t begin until July 1 – teams are technically not allowed to contact players until that start date – there will still be plenty of tampering and back-channeling that will lead to a flurry of reported deals within the first few hours of the signing period. The Bucks, who could be losing as many as eight free agents, figure to be active well before the clock strikes midnight.

Odds Milwaukee re-signs Khris Middleton?

Relatively high. When thinking about Middleton’s pending free agency, I keep coming back to this quote general manager Jon Horst gave to reporter Kane Pitman earlier this month:

Spent some time with Bucks GM, Jon Horst this morning. During the discussion, Khris Middleton’s pending free agency came up. Horst’s response was pretty clear. pic.twitter.com/GPpSMmJa2x — Kane Pitman (@mkebucksaus) May 1, 2019

I find it pretty unlikely that Horst would give that quote without some sort of sense that the two sides will be able to come to a deal. Middleton isn’t technically a free agent, but he is widely expected to turn down his $13 million player option for 2019-20 and hit the open market. The question is: What type of dollar figure will Middleton command with so many teams around the league flush with cash and looking for a secondary star?

The salary cap is expected to rise to $109 million for 2019-20. If Middleton opts out as projected, Milwaukee can get to roughly $39 million in cap space (the Bucks would have to move on from George Hill by July 2 to get to the number, but doing so would save them $17 million. Seems like a no-brainer.) Middleton can earn up to 30 percent of the cap as a max-level player on his next contract, which turns into roughly $32 million in 2019-20. (His salary would keep climbing alongside the rising cap in future years as well.)

The Bucks probably do not want to offer Middleton that much money, but as the game of musical chairs goes on, and teams become increasingly desperate to land an All-Star, it seems likely someone will pony up enough cash to make Milwaukee blink. Here’s guessing Middleton is back in the green and cream next season on something very close to a max deal.

Malcolm Brogdon’s status?

Decidedly more dicey. Brogdon turned into an absolutely vital cog for the Bucks this season, becoming just the eighth player to post a 50-40-90 season in league history, and putting together a nice run in the postseason once he returned from his foot injury. Of course, other teams noticed this as well and likely started thinking about how the versatile, sweet-shooting guard with ball-handling chops and defensive toughness would fit within their own scheme.

Brogdon, 26, fits perfectly in any system and should have a bevy of suitors this summer. (Atlanta, who will have acres of cap space and a need for a backcourt partner next to the diminutive Trae Young, comes to mind.)

The former Virginia guard is a restricted free agent, so the Bucks will be able to match any offer that comes his way. Based on Giannis Antetokounmpo’s recent comments and the front office’s increasingly painful thought of losing a second round pick that the Bucks developed into a borderline All-Star, I expect Milwaukee to hold its nose and retain Brogdon, unless the bidding climbs to a truly unpalatable number. Rival teams may load a potential Brogdon contract with nasty clauses and trade kickers knowing full-well the Bucks will match regardless, forcing Milwaukee to deal with the contractual repercussions (similar to what the Brooklyn Nets did to the Washington Wizards during Otto Porter’s restricted free agency in 2017).

Is Splash Mountain on the move?

Most likely. Brook Lopez turned into the best offseason signing of the year, piling up 12.5 points and 2.2 blocks a night on 37 percent three-point shooting for less than $3.4 million. With potential Middleton and Brogdon contracts launching the Bucks into the luxury tax, there probably will not enough petty cash lying around the practice facility to fund a Lopez return, who could be looking at a multi-year contract worth 10 figures annually.

Lopez has earned over $120 million in his career thus far and just participated in more playoff games in the last six weeks than he had in his in his first 10 NBA seasons, so maybe he is willing to sacrifice a little to remain with a competitive team. But after already taking one below-market deal last summer, he would be hard-pressed to pass up a potential long-term offer elsewhere at age 31.

If this indeed is the last we see of the Splash Mountain in Milwaukee, it’s truly been an honor. Lopez went out on top, leading the Bucks to a Game 1 victory in the franchise’s first ECF in nearly two decades, which he backed up with 13 points in the fourth quarter of Game 6 as the Bucks made one last-gasp effort to stay in the series. Hats off to you, sir.

Will either George Hill or Nikola Mirotic return?

Don’t see it. For as well as Hill played in the postseason – he averaged 12-4-3 in 26 minutes per game – the opportunity to save $17 million on a backup point guard is too great for Milwaukee to pass up. Maybe he can come to an agreement with the Bucks at a much smaller cap figure, but he’s probably in the same boat as Lopez. At 33 years old, this is probably Hill’s last chance to grab a multi-year deal.

As for Mirotic, his Game 6 benching may be the last we see of the Montenegro native in a Milwaukee uniform. The Bucks seemingly stole Mirotic at the trade deadline, and he got off to a nice start with the Bucks before missing the final 11 regular season games with an injury. He returned for the playoffs and moved into the starting lineup after the Game 1 defeat to Boston in the second round. But he never truly found his footing with the Bucks – which isn’t surprising, as he played just 14 regular season games with them – and ended up shooting just 29 percent from distance in the postseason until head coach Mike Budenholzer deemed him unplayable down the stretch of the Toronto series. Ersan Ilyasova and DJ Wilson will once again pick up the bulk of the power forward minutes off the bench if Mirotic moves on in 2019-20.

Do the Bucks already regret that Eric Bledsoe extension?

Probably not, but they can’t be feeling great about it. Bledsoe looked like a new man in Budenholzer’s system this year, and eventually inked a four-year, $70 million extension in March, right before turning back into the playoff pumpkin we saw last spring against Boston. Bledsoe has now shot just 42 percent across 22 postseason games during the last two years. Losing Hill, who saved Bledsoe’s hide on several occasions during the Boston series this year, will just put even more of an onus on the 29-year-old.

Now, it’s really not all bad. Bledsoe did put together an impressive regular season campaign, and even with the extension, his average annual salary still only equates to 12th among all point guards, which is about where he ranks in his peer group. He also just landed on the all-defensive first-team, a skill that still shined through in the postseason amidst his offensive inconsistencies. Relying on Bledsoe will always feel like a heart attack is on the horizon, but the contract is fair for both sides.

Does Giannis have another level?

Of course. I’m going to need Antetokounmpo to actually plateau before I predict any stagnation will happen. And heading into his age-25 campaign, after already adding weapons to his arsenal with each passing offseason, it’s a safe bet he’ll find a way to make another mini-leap.

Giannis’ obvious weakness is his jumper, though he started to show positive development from long range this year, hitting 33 percent of his threes after Christmas all the way through the postseason. Defenders will always sag off him because he attacks the rim so ferociously, but he could follow the career arc of his Eastern Conference predecessor, LeBron James. LeBron was only a 33 percent shooter from beyond the arc through his age-26 season, but truly became unguardable over the next seven seasons when his three-point shooting ticked upward. (He hit over 35 percent of his treys in six of those seasons.)

Antetokounmpo isn’t quite the shooter young LeBron was, yet after struggling mightily for the first two months of the season, Giannis at least proved he is not a lost cause from deep over the final two-thirds of 2018-19. He has several paths to making his offensive game less predictable in high-leverage situations, but finding a consistent three-point shot is certainly the easiest route available.

When is the NBA Draft?

June 20. The Bucks only have one pick, no. 30 to conclude the first round.

Draft night possibilities?

The Bucks have largely struck out in the first round since drafting Giannis in 2013, though the story is not yet complete on DJ Wilson and Donte DiVincenzo. The 2019 draft figures to be one of the most unpredictable in recent memory, as its lack of depth means each prospect comes down to the eye of the beholder. Here are some names that could still be available when Milwaukee is on the clock:

• Matisse Thybulle (Washington): historically great defensive wing stopper

• Bruno Fernando (Maryland): offensive-minded big man with no defensive instincts

• Nic Claxton (Georgia): point center

• Luguentz Dort (Arizona State): high-energy, score-first combo guard

• Talen Horton-Tucker (Iowa State): versatile 18-year-old with a miles-long wingspan

• Dylan Windler (Belmont): dead-eye shooter with size

• Ty Jerome (Virginia): middle-class Malcolm Brogdon
  

Predicting who will even be available at no. 30 – much less who the Bucks will pick – is near impossible this far out from draft day, though Milwaukee’s ultimate selection could foreshadow potential free agency moves less than two weeks later.