Which Upgrades will the Bucks Pursue This Offseason?


Usually, autumn weather indicates that the NBA is preparing for the start of another regular season. This year (as we all know) doesn’t have that sentiment, but a frantic and shortened offseason will precede December 22nd’s opening night. The Milwaukee Bucks will undoubtedly look to be aggressive when transaction restrictions are lifted, as they have the most important assignment ahead– netting Giannis Antetokounmpo some more help.


The immense pressure for the Bucks to earn the Larry O’Brien Championship Trophy (the biggest missing piece) has created a delicate process of contemplating the roster. Considering the underwhelming star power that has accompanied Giannis, it’s painfully evident that Milwaukee needs an upgrade. Placing another elite scorer alongside Khris Middleton to aid Giannis is essential.

The Bucks will once again be deemed Eastern Conference favorites, and additional offensive security can elevate an already championship-caliber team to be next season’s overall frontrunner. The free agency pool is visibly shallower compared to last year’s frenzy, but there are undoubtedly players that the Bucks desire.

The following players all have the viability to fit the Bucks’ system while being affordable in Milwaukee’s budget.

DeMar DeRozan & Patty Mills

Imagine DeMar DeRozan’s successful revenge on his former team in Toronto by winning a championship with Milwaukee. While it’s a scenario that many Bucks fans may view as unlikely, it is realistic.

DeRozan is entering the final season of his five-year, $139M contract with the San Antonio Spurs. After missing bubble play during this season’s restart, San Antonio appears to be heading deeper into a rebuilding process, and DeRozan is perhaps the team’s most valuable trading option.

Eric Bledsoe will likely headline most trade packages the Bucks offer. Bledsoe, who averaged 14.9 PPG, 4.6 REB and 5.4 AST last season, has struggled massively in his playoff tenure with the Bucks. The Spurs, however, have Dejounte Murray as their point guard of the future, so Bledsoe may not be of keen interest. On the other hand, Bledsoe’s defensive tenacity could compliment Murray’s game nicely as dual starters. This scenario would also leave the Spurs with developing guard Derrick White as an interchangeable option. That is, of course, if the Bucks could lure veteran guard Patty Mills into the package.

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Mills Another Option

Mills is entering the last season of his four-year, $48M contract with San Antonio. Patty, who averaged a career-best 11.6 PPG last season, is statistically a downgrade from Bledsoe. What the Bucks gain in Mills is a tremendously hard-working, skilled and knowledgeable veteran who won a championship in 2014.

A presentable offer the Bucks can make the Spurs:

  • Eric Bledsoe
  • Ersan Ilyasova
  • D.J. Wilson
  • 2020 1st round pick (via IND)
  • 2023 2nd round pick


  • DeMar DeRozan
  • Patty Mills
  • Chemezi Metu

The Deer would instantly have one of the most prominent big threes in the NBA with Antetokounmpo, Middleton and DeRozan, along with an experienced Patty Mills running the point. DeRozan and Mills will cost just under $40M next season, adding roughly an additional $12M to Milwaukee’s tab for 2020-21.


The New Orleans Pelicans handed the Los Angeles Lakers an NBA title last offseason by trading Anthony Davis, so why can’t they help out the Bucks too?

Pelicans forward Brandon Ingram anticipates a cosmic offer to stay in the Big Easy, which may end the bidding war before it begins. Milwaukee, however, could strong-arm the Pelicans by showcasing their eliteness. The Bucks have “win-now” expectations while the Pelicans still have a young prospering squad expected to survive in the Western Conference.

Ingram’s best chance at a ring is in Milwaukee, not New Orleans. This fact is even more likely if the Bucks trade for teammate Jrue Holiday, a player fans have desired for years.

Holiday will begin the 2020-21 season on the fourth year of his five-year, $131.8M contract. The Pelicans guard, who averaged 19.1 PPG, 4.8 REB and 6.7 AST during the regular season, is an offensive boost to Bledsoe. Adding Ingram’s 23.8 PPG is a mammoth replacement to Wesley Matthews’ 7.4 PPG as well. The Bucks can offer an experienced guard in Bledsoe, the same age as Holiday (30), with added young talent to coincide with the Pelicans’ future development.

A presentable offer the Bucks can make the Pelicans:

  • Eric Bledsoe
  • Ersan Ilyasova
  • D.J. Wilson
  • Sterling Brown (sign-and-trade)


  • Jrue Holiday
  • 2021 2nd round pick

Offensively, the Bucks would become a monstrous force with four of their starters averaging over 19 PPG during the 2019-20 season.


One of the earliest rumors summoned from social media was the Bucks’ interest in Thunder guard Chris Paul. Despite separate claims that both Antetokounmpo and Paul want to play with each other, it appears unlikely. Chris Paul’s 35 years of age and whopping $40M+ over each of the next two seasons underlines Milwaukee’s reluctance, while teams like the Phoenix Suns may be more willing to execute a deal.

Financially, the Bucks could afford a trade for Paul, who put up 17.6 PPG, 5.0 REB and 6.7 AST in 70 games for Oklahoma City last season. Considering they would have to offer a lengthy trade package, Milwaukee would clear needed cap space while maintaining room for another free-agency signing.

While a healthy Chris Paul running an offense with the Greek Freak portrays the winningest image, the entire operation would plummet with an injury. Nevertheless, if this signing is what it takes to obtain Giannis’ signature, the Bucks have no choice but to make the move.

A presentable (Giannis approved) offer the Bucks can make the Thunder for CP3:

  • Eric Bledsoe
  • George Hill
  • Ersan Ilyasova
  • D.J. Wilson
  • Frank Mason III (sign-and-trade)
  • 2020 1st round pick (via IND)
  • 2022 2nd round pick

Conclusively, seven players for a possible one-year rental is normally ill-advised for a small-market franchise, but this situation is different given the championship aspirations Paul is seeking.


Let’s assume the Bucks execute one of these trades or sign an elite free agent; they’ll still need more scoring. Kyle Korver, Sterling Brown and Pat Connaughton are all free agents that did not produce much offense for the Deer this season. Wesley Matthews has an outstanding $2.6M player option, leaving Milwaukee with a vacancy at shooting guard should he decline and elect free agency.

During the regular season, Joe Harris averaged 14.5 PPG, 4.3 REB and 2.1 AST for the Brooklyn Nets. Adding a three-point shooter like Harris to coincide with Middleton will elevate the Deer’s offense while alleviating Giannis’ normal pressure.

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Now that Kevin Durant and Kyrie Irving can take over Brooklyn, it’s logical that Harris might want to sign elsewhere. Milwaukee could offer Harris a starting role while obtaining an affordable contract as well.


Whispers pertaining to the Bucks’ interest in Kings restricted free agent Bogdan Bogdanovic have also circulated. Akin to the Joe Harris scenario, a Bogdanovic acquisition would serve as a compliment to a much grander move made by the Bucks. Hoping to satisfy the Freak, this can’t be the lone creative gesture executed by Milwaukee’s front office.

Acquiring Bogdanovic, who averaged 15.1 PPG, 3.4 REB and 3.4 AST during the 2019-20 season, would add additional scoring insurance and potentially round-out Milwaukee’s starting lineup.

It has also been reported that forward Harrison Barnes, who is entering the second year of his four-year, $85M contract, could be shopped by Sacramento as well. However, obtaining both players would be tough without Eric Bledsoe being sent in return. Paying Bogdanovic and Barnes together over $30M next season without adding an elite point guard seems ridiculous for Milwaukee to consider.


Additional speculation is the Bucks’ interest in Pacers guard Victor Oladipo. Although a proven veteran, Oladipo has only played in 55 games over the previous two seasons due to injury, which could scare Milwaukee out of consideration.

Oladipo has averaged 17.3 PPG, 4.6 REB and 3.9 AST during his NBA career. With an expiring $21 million next season, Oladipo would cost roughly the same as Harrison Barnes. Nonetheless, assuming the Pacers are at all interested in a Malcolm Brogdon-Eric Bledsoe reunion is a baffling prediction. A third team would surely need to be involved, or (if attainable) the Bucks could test their luck with a Bledsoe-less offer and ultimately net a steal against a division rival.

A presentable Eric Bledsoe-less offer the Bucks can make for Oladipo

  • Donte DiVincenzo
  • Ersan Ilyasova
  • Pat Connaughton (sign-and-trade)
  • D.J. Wilson
  • 2022 second-round pick


  • Victor Oladipo

An Oladipo acquisition without having to deal away Bledsoe or Brook Lopez would be monumental for Milwaukee. The Bucks could then explore (if they haven’t already) a suiting team for Bledsoe and continue pursuing supplementary scoring options.


This would be amazing. Milwaukee adding another sharp-shooting forward to their rotation would be a problem for the rest of the league, especially if the Bucks had already upgraded at point guard.

Gallinari averaged 18.7 PPG, 5.2 REB and 1.9 APG in 62 games for the Thunder last season. The 12-year veteran has predominantly shifted into a stretch four over the course of his career, which creates options for head coach Mike Budenholzer. Interchanging Giannis, Brook and Gallinari between the three, four and five spots on the floor could be a challenging, yet rewarding effort.

Gallinari earned $22.6M last season in Oklahoma City, but reportedly will be prioritizing winning over getting paid. This bodes well for the Bucks, but they surely won’t be the only interested party.

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About Mike Konicek

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