Honestly, the way most people talk about Matthew Dellavedova’s time with the Milwaukee Bucks, you’d think he just cashed a check and vanished into the Wisconsin winter. It’s always the same story: the Bucks "overpaid" for him after he rode LeBron James’s coattails in Cleveland, he got injured, and then he was shipped back to the Cavs like a lost Amazon package.
But that’s a lazy way to look at it.
If you actually look at the 2016 NBA landscape, the Bucks didn't just want a point guard. They wanted a specific brand of madness. They needed a guy who would dive for a loose ball in a preseason game like it was Game 7 of the Finals. They needed "Delly."
The $38 Million Gamble
Back in July 2016, the Bucks signed Dellavedova to a four-year, $38.4 million offer sheet. At the time, social media went into a full meltdown. People were losing their minds over an undrafted Aussie getting nearly ten million a year. But here’s the thing: Milwaukee was desperate for a culture shift. Giannis Antetokounmpo was just starting to turn into The Greek Freak, and the front office wanted a veteran who knew how to win.
Delly had just come off a title with Cleveland. He was the guy who famously defended Stephen Curry so hard in 2015 that he ended up in the hospital on an IV drip. Milwaukee wasn't paying for 20 points a game; they were paying for that specific, borderline-reckless intensity.
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Why the Fit Sorta Worked (Until It Didn’t)
In his first season in Milwaukee (2016-17), Delly actually started 54 games. He averaged a career-high 7.6 points and 4.7 assists. He was basically the adult in the room for a very young, very raw roster.
The plan was simple. Giannis would handle the ball, and Delly would be the "3-and-D" point guard who didn't need the rock to be effective. And for a while, it worked. He shot roughly 37% from deep that year. He organized the defense. He screamed at guys when they missed rotations.
But then the injuries started piling up.
Hamstrings. Knees. Concussions. By the 2017-18 season, his minutes dropped to 18 per game. He played only 38 games total. The "grit" that made him famous was also breaking his body down. When Mike Budenholzer took over as coach in 2018, the Bucks transitioned to a high-pace, athletic system that prioritized length and speed. A 6'3" guard who played like a middle-linebacker didn't really fit the "Let it Fly" era anymore.
The Trade Back to Cleveland
By December 2018, the writing was on the wall. Milwaukee needed to shed salary and find more explosive playmaking. They sent Dellavedova back to Cleveland in a three-team trade that brought back George Hill and Jason Smith.
Most fans saw it as a "failed" era. But if you ask the guys who were in that locker room—guys like Khris Middleton or a young Giannis—they’ll tell you Delly’s impact stuck around. He set a standard for how to practice. He showed them that being "annoying" on defense was a skill, not a flaw.
Where is Matthew Dellavedova Now?
Fast forward to 2026, and Delly is still out there grinding, though not in the NBA. After a brief return to the league with the Sacramento Kings in 2022-23, he headed back home to Australia's NBL.
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As of early 2026, he’s playing for the Sydney Kings under legendary coach Brian Goorjian. Even at 35, he’s still the same guy. He recently suffered a concussion in a match against Melbourne United, which has sidelined him for the upcoming HoopsFest clash with Brisbane. It’s classic Delly—he only knows how to play at one speed, and sometimes that comes with a price.
Actionable Insights for Bucks Fans
If you're still tracking the legacy of the "Delly Era" in Milwaukee, here is what you should actually take away:
- Don't judge the contract by the box score: The $38 million wasn't for stats; it was for the professional habits he taught a championship core during their developmental years.
- Watch the NBL transition: If you want to see how veteran NBA guards age, watch Delly’s current run in Sydney. He’s shifted from a defensive pest to a high-level floor general (averaging over 7 assists last season).
- Respect the "Undrafted" Path: Dellavedova remains one of the best examples of how basketball IQ and conditioning can overcome a lack of elite athleticism.
The Bucks eventually got their ring in 2021, and while Delly wasn't on that specific roster, he was a massive part of the foundation that taught Milwaukee how to stop being "the team of the future" and start being a team that wins.