Milwaukee Bucks: Taking big swings comes with harsh difficulties

MILWAUKEE, WI - JANUARY 22: (Photo by Gary Dineen/NBAE via Getty Images)
MILWAUKEE, WI - JANUARY 22: (Photo by Gary Dineen/NBAE via Getty Images)

Under general manager Jon Horst, the Milwaukee Bucks have been aggressive in building up their roster. Whether they will do so again this offseason is the big question.

Nearing on a month since the disappointing end to their 2019-20 season, all sorts of speculation has run rampant surrounding the Milwaukee Bucks.

The immediate fears in regards to Giannis Antetokounmpo’s present and future set off a firestorm of discussion that has since quieted down in light of the Bucks’ latest playoff disappointment. Antetokounmpo has even gone to great lengths of expressing his happiness of being in Milwaukee, all while applying the pressure of wanting to remain a winner and fighting for the ultimate goal of winning an NBA title.

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That adage will inform how the Bucks’ front office and general manager Jon Horst will have to attack this offseason in order to not take further steps back in their pursuit of a title.

Under Horst’s tenure, the Bucks have shown a willingness to be aggressive at opportune times. The deal for Eric Bledsoe gave the Bucks a chance to fortify their backcourt, especially when they were in need of another ball handler and steely defensive presence, at the expense of a couple of protected draft picks.

That same aggressiveness showed itself during the 2019 NBA trade deadline where the Bucks dealt for Nikola Mirotic from the New Orleans Pelicans after a series of maneuvers and accumulating draft picks eventually went the Pelicans’ way. For as much as trading for Mirotic crashed and burned, the Bucks had to load up amid the proverbial arms race going on between the top teams in that year’s Eastern Conference race.

Now as the balance of power appears to be shifting again at the top of the East and with the Bucks backed in quite the corner after their Conference Semifinals humiliation, the team faces their greatest challenge of the last two seasons.

How they go about addressing that challenge, the least of which revolves around potentially upgrading on Bledsoe, is on the minds of many. So is Bucks ownership’s willingness to spend and go into the luxury tax as co-owner Marc Lasry pledged to do with Antetokounmpo in a reported meeting after the end of the season.

It’s within that general framework that Horst and the rest of the front office have to operate from, on top of the limited draft assets and cap resources they have available to them.

The Bucks may have to fill up to seven roster spots this offseason, depending on the futures of Sterling Brown (restricted free agent) Ersan Ilyasova (non-guaranteed salary), Robin Lopez and Wesley Matthews (player options). That’s not counting their two-way slots, which, given the uncertainty of next season’s G League campaign amid the coronavrius pandemic, won’t be the biggest priority to fill.

The dynamic surrounding Bledsoe as well as as the conversation to upgrade on him with star-level names is incredibly fraught with complications on numerous levels. That applies from a salary perspective as he’s due $59 million over the next three years and the questions over which trade partner will step up to take on Bledsoe in light of his extensive playoff struggles. After all, building up a trade package is a two-way street.

With plenty of more going on at work and behind the scenes that have yet to surface, to say that the walls are closing in on the Bucks may sound a little dramatic. But when it comes to how they can retool and reshape their foundation around Antetokounmpo as well as Brook Lopez and Khris Middleton, their options are far more limited than they anticipated.

Could that always change down the line? Absolutely. We’ve recently seen NBA teams in greater binds financially acquire upgrades via trade, as was the case with the Heat last summer when they brought in Jimmy Butler. And of the many details that have come from that aforementioned meeting between Lasry and Antetokounmpo, seeking creative ways to find upgrades may be on the table this offseason.

But aside from the creativity that it requires to pull of such a move, the Bucks will be asking themselves how willing they are to push the boundaries on shaking up their continuity and foundation for someone that might shake up their current system around Antetokounmpo. It’s along that line of thinking that the organization has reportedly ruled out swinging for a Chris Paul trade.

Simply put, there are no easy paths towards the Bucks addressing the many issues that ail them at the moment. And ultimately, what the team does will be guided by management’s willingness to shake up the progress and continuity they have built to get to this point in the first place.