Everyone remembers where they were when the 2016 NBA free agency frenzy kicked off. The cap spiked, money was flying everywhere, and suddenly, role players were getting paid like franchise cornerstones. In the middle of that chaos, the Matthew Dellavedova Milwaukee Bucks era began with a massive four-year, $38.4 million offer sheet.
It felt like a heist for the Bucks at the time. They were getting a "Curry Stopper," a guy fresh off an NBA Championship with the Cleveland Cavaliers, and someone who LeBron James himself publicly congratulated for getting his bag. But hindsight in the NBA is a brutal teacher.
Looking back, that contract became a symbol of a very specific, weird time in Milwaukee basketball history. It wasn't just about the points or the assists; it was about trying to find a culture setter for a young Giannis Antetokounmpo. Honestly, it sorta worked—until it didn't.
The Scrappy Aussie Arrives in Cream City
When Delly landed in Milwaukee, the vibe was electric. You had this undrafted kid from Maryborough who had basically willed himself into becoming a household name by diving for loose balls and annoying the hell out of the Golden State Warriors. The Bucks needed that. They were young, talented, and lacked that "dirt under the fingernails" grit that Dellavedova specialized in.
Milwaukee didn't just sign him; they traded for him in a sign-and-trade deal to make the math work, sending cash and the rights to Albert Miralles to Cleveland. This move hard-capped the Bucks, showing just how much they valued his presence.
In his first season (2016-17), Delly actually put up decent numbers. He started 54 games and averaged 7.6 points and 4.7 assists. He was the adult in the room. He spent a lot of time mentoring a rookie named Malcolm Brogdon, which, if you think about it, might be his biggest contribution to the franchise. Brogdon ended up winning Rookie of the Year, and some of that "Delly-prep" surely rubbed off.
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Why the Matthew Dellavedova Milwaukee Bucks Experiment Stalled
The wheels started coming off because of two things: injuries and the "Giannis Leap."
As Giannis Antetokounmpo transformed from a skinny prospect into a primary playmaker, the need for a traditional, ball-dominant backup point guard who couldn't reliably create his own shot started to fade. Delly was a great secondary distributor, but he wasn't a floor spacer who could keep defenses honest when the Greek Freak was charging down the lane.
Then there were the health issues.
- 2017-18 Season: Delly missed huge chunks of time with knee and ankle problems. He only played 38 games.
- The Concussion History: This is the part people often forget. Delly’s "go for broke" style of play led to some nasty collisions. He dealt with lingering concussion symptoms that sapped his aggressiveness.
- The Contract Weight: By year three, that $9.5 million annual salary looked like a mountain on the Bucks' books. They needed more production for that price tag.
By December 2018, the experiment was over. Milwaukee shipped him back to Cleveland in a three-team trade that brought back George Hill and Jason Smith. It was a business move, plain and simple. The Bucks needed to clear cap space and find a veteran who fit the Mike Budenholzer system better. George Hill ended up being a massive piece for their deep playoff runs, while Delly went back to the place where he was a legend.
What Most People Get Wrong About Delly's Legacy
People love to call that contract a "bust." I think that's a bit harsh.
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If you look at the Matthew Dellavedova Milwaukee Bucks stats, sure, they aren't mind-blowing. He shot about 39% from the field during his time there. But you can't measure the value of a guy who shows a 22-year-old Giannis how to take care of his body or how to study film. Delly was a professional's professional.
He didn't fail because he was bad at basketball; he failed to live up to a contract that was inflated by a once-in-a-lifetime cap spike. In 2026, we see this all the time—teams overpaying for "culture guys" and then regretting the cap hit two years later.
Life After the Bucks: The NBL and Beyond
It is actually pretty wild to see where he is now. As of early 2026, Delly is still grinding, but back home in Australia. After a stint with the Sacramento Kings where he proved he could still contribute in a locker room, he returned to the NBL.
He spent time with Melbourne United, leading them to some deep playoff runs and even winning the Larry Sengstock Trophy as the NBL Grand Final MVP in 2025, despite his team losing the series. Talk about a "Delly" stat—playing so hard in a loss that you're still the best player on the floor.
Currently, he's with the Sydney Kings, though he's recently been sidelined by—you guessed it—a concussion. It happened just a few days ago in a clash with Melbourne United. At 35, you have to wonder how many more of those hits he can take. He’s been through the ringer.
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Actionable Takeaways for Bucks Fans and Analysts
If we're looking at the Matthew Dellavedova Milwaukee Bucks tenure as a case study, here is what we can actually learn:
- Beware the "Playoff Bump": Never overpay for a role player based solely on one or two high-intensity playoff series. Delly’s 2015 Finals performance was legendary, but it wasn't his "average" level of play.
- System Fit Over Grit: Grit is great, but in the modern NBA, if you’re a guard who can’t shoot 40% from three or finish at the rim over length, you’re going to struggle when the star player needs space.
- Veteran Value is Real: Even though the contract was an overpay, having veterans like Delly around during the formative years of a superstar (Giannis) is an investment that usually pays off in ways the box score can't track.
The Matthew Dellavedova story in Milwaukee wasn't a fairy tale, but it wasn't a disaster either. It was a bridge. A bridge from the "Bucks Venture" years to the "Championship Contender" years. He taught them how to play hard, and then he moved out of the way so they could fly.
To really understand how the Bucks built their current culture, you have to look at the guys who were there before the rings. Delly was one of the loudest voices in that locker room when the foundation was being poured. That’s worth more than the $38 million, even if the fans at the Bradley Center (and later Fiserv Forum) wanted more triples and fewer turnovers.
Next Steps for Deep-Diving Fans:
- Check out the 2016-2018 Bucks roster turnover to see how they eventually flipped those mid-tier contracts into the 2021 Championship core.
- Monitor the NBL injury reports regarding Delly's current status with the Sydney Kings; his availability for the 2026 playoffs remains a massive storyline in Australian basketball.