Milwaukee Bucks: Jon Horst faces his tallest task yet this offseason

Jon Horst has been fantastic since being appointed as the Milwaukee Bucks’ general manager, but he will soon face his toughest challenge yet.

Since taking over as general manager in the summer of 2017, Jon Horst has done a stellar job constructing aspects of this Milwaukee Bucks roster.

Horst has been at the center of many foundational moves, whether it’s been bringing in head coach Mike Budenholzer, the coup that was signing Brook Lopez, acquiring George Hill, and a slew of other moves to put the team in their current position. For those efforts, Horst took home Executive of the Year honors and followed that up with a fourth-place finish this year.

Although he has also made some questionable moves in his tenure, the 37-year-old has been an instrumental piece in orchestrating Milwaukee’s recent success. Now, as the Bucks prepare for another title run, Horst will have his toughest task to date this offseason.

The center of his challenges will revolve around Giannis Antetokounmpo, who is eligible for a supermax extension worth upwards of $220 million. As much as everyone in the city of Milwaukee would like to get the two-time MVP signed on for the long-haul, there are reasons why that might not happen at the opening of free agency or at all this offseason.

As described by ESPN’s Brian Windhorst on The Alex Kennedy Podcast on BasketballNews.com, signing doesn’t pose that much of an incentive for the Greek Freak as opposed to playing out the final year of his current deal.

“But here’s the harsh truth for the Milwaukee fans and this is upsetting, I know, but it’s just true. There’s no advantage for Giannis to signing this offseason. He can get the exact same contract from the Bucks a year from now and the only thing that you’re doing by re-signing now is giving comfort to the Bucks. I’m not saying he shouldn’t do that. If I was his agent, I would not recommend that he would sign it. I know that there’s the question of ‘Well, what if (Giannis) gets injured?’ I would say any injury that you would have, he would still get that contract from the Bucks.”

While not set in stone, that assessment from Windhorst is likely the reality of the Antetokounmpo situation. If Antetokounmpo indeed intends to take that route, the 2020-21 season is championship-or-bust for the Milwaukee Bucks and another disappointing playoff finish would certainly be detrimental to the team’s chances of re-signing the two-time MVP.

Jon Horst will need to get creative in retooling the roster to put together a championship-caliber unit for Milwaukee Bucks.

With a lackluster free agent class on the horizon, the trade market will be very active this offseason, and the Milwaukee Bucks will partake. Milwaukee’s desire to upgrade the roster has been a topic of discussion since their season ended and will certainly ramp up in the coming months.

The most prominent storyline, aside from Antetokounmpo, revolves around starting point guard Eric Bledsoe. As many expected, it is an “open secret” that the Bucks will look to move him this offseason, but trading the 30-year-old is far easier said than done. With the guard’s postseason woes and  his hefty contract over the next few years looming large, trading Bledsoe will not be an effortless task.

What other kinds of moves might be on Jon Horst’s to-do list this offseason are unknown at this point, but this current roster will likely look very different by the time next season rolls around. Horst has pulled off some exceptional moves in the past, and Milwaukee will need him to find some success this offseason in the same light to put them in the best position to succeed next year.

Everyone within the organization knows what is at stake this offseason and next season as Giannis ponders his future with the franchise. As Antetokounmpo detailed it to TNT’s Ernie Johnson as he accepted his second consecutive MVP award:

“As long as everybody is on the same page and as long as everybody is fighting for the same thing every single day, which is to be a champion, I don’t see why not be in Milwaukee for the next 15 years.”

Another 15 years or so of Giannis Antetokounmpo in a Milwaukee Bucks uniform undoubtedly sounds good. While that decision will not fall solely on the shoulders of Horst and company, they do play a part in it ensuring that is a reality. No pressure.