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Home»Basketball»On this day in Bucks history: Milwaukee signs Bobby Simmons
Basketball

On this day in Bucks history: Milwaukee signs Bobby Simmons

News RoomBy News RoomAugust 8, 2026No Comments6 Mins Read
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On this day in Bucks history: Milwaukee signs Bobby Simmons

I can remember it vividly. Year 11 (junior year to most of you). My best friend’s voice riding the wind across the yard.

“Did you see it?”

I looked up, mouth ajar, eyes staring as if I was mid matrices exam. Then the follow-up.

“The Bucks have signed Bobby Simmons!”

Dilation. Pupils, mouth. Everything.

It was true. A quick—okay, slow (we’re talking ADSL speeds)—Google search (or was it Ask Jeeves?) confirmed the news. The NBA’s reigning Most Improved Player (MIP), coming off a season in which he averaged 16.4 PPG, 5.9 RPG, 2.7 APG, and 1.4 SPG on .466/.435/.846 shooting, was joining the Bucks on a 5-year $47m contract.

And they were movin’ on up.

The promise

My excitement was palpable, even as a closet fan. Coming off a 25th-placed 30-52 season the year prior, Simmons’ arrival signalled change and upward trajectory in Milwaukee. But he wasn’t alone. T.J. Ford—yes, that new assistant coach—was back after missing his entire sophomore season due to a severe spinal injury, Michael Redd had just re-signed on a six-year deal (remember those?), and Andrew Bogut had arrived in town after being selected with the number one overall pick in the NBA Draft. Youth and promise. Sounds familiar, right? Oh, and they had a new coach too, moving off one Terry (Porter) for another (Stotts).

But the roster revitalisation wasn’t done. Not yet. Two months later, Milwaukee would trade for All-Star centre Jamaal Magloire in a deal that sent out Desmond Mason and a 2006 first-round pick (that would become Cedric Simmons). And just like that, the starters were set: two seven-footers up front, a big-bodied forward on the wing, a sweet-shooting two, and an exciting, young point. Read that sentence again and you could easily confuse it for this year’s squad.

So, with a revamped starting five that also strengthened the bench—2004-05 starters Joe Smith, Mo Williams, and Dan Gadzuric became reserves—the Bucks looked primed for a playoff push.

Bright beginnings

The season started with a bang—a 117-108 overtime win against the Philadelphia 76ers—and Simmons looked every bit the key free agent signing Bucks fans had hoped for, dropping 22 points to go along with a career-high-tying 12 rebounds. Up next, New Jersey. Kidd, Vince, RJ. SEGABABA. And when my best mate told me he’d organised his next door neighbour to record it on VHS for us (it was our only access to full NBA games), I became Bango after nailing an overhead half-court shot.

We watched it that afternoon (time difference and all that), dragging dining chairs into the corner of his room so we could get as close as possible to his box TV. The mid-2000s style meant every basket was a grind, and when Dan Gadzuric hit the Bucks’ first field goal—an isolation, face-up jumper from the left block with 6:43 on the clock to make it a 9-3 Nets lead—I could finally move off the front of the chair. At the end of the first, the Nets led 29-17. By halftime, it was 55-50 and Simmons had gone just 1/6 from the field. He didn’t improve much after the break, missing his only attempt, but a 33-point second-half explosion by Redd secured a Bucks victory. Enthused, we chucked NBA Live into his PlayStation 2, let our inner Larry Harrises out, and had at it.

Three nights later, Simmons looked back to his Opening Night self, putting up 23 points, four rebounds, and three assists to lead the Bucks over D-Wade and the Miami Heat, giving Milwaukee their first three-game winning streak to start the season since 2001-02. They remained hot too. By mid-December, the Bucks were 12-7. By the New Year, they were 17-11. And despite cooling off by the time All-Star break came around, they remained in the black: 27-25.

Simmons, however, wasn’t quite living up to expectations, regressing statistically across the board thanks in large part to the inconsistent play his opening three games foreshadowed. 20 points one night become single digits the next. And across the season’s first three months, he seemed to be hurting more than he was helping (a plus/minus of -46). He would amend that on the back of a season-high 26 points (including 5/9 from three) in a two-point loss to the Houston Rockets to begin February, finishing the second half of the season at +95 despite the Bucks going just 17-20 over this stretch.

Overall, Simmons’ first year with the Bucks was solid if unspectacular: 13.4 PPG, 4.4 RPG, 2.3 APG, and 1.1 SPG on .453/.420/.825 splits. More importantly, the Bucks had made good on that playoff promise.

A post-season taster

Despite the excitement, Milwaukee’s playoff run didn’t last long. Playing the second-seeded “Goin’ to Work” Detroit Pistons—Ben Wallace, Rasheed Wallace, Tayshaun Prince, Rip Hamilton, and Chauncey Billups—the Bucks were beaten in a gentleman’s sweep, experiencing their only taste of victory in Game 3 thanks to a combined 60 points on absurd 23/31 shooting from Redd and Williams, and a team-leading seven rebounds and 15 assists from Ford. Simmons chipped in with a steady 10 points, four boards, and three assists.

Across the series, though, to say he struggled would be an understatement. In his first taste of post-season action, Simmons was held to just 6.6 PPG, 3.6 RPG, 2.0 APG, and 1.8 SPG, shooting a paltry 33% from the field while not attempting a single free throw, despite playing 31.8 MPG. Still, it was a season of growth and Simmons and the Bucks headed into the offseason full of optimism.

The E.N.D.

Despite being released in 2009, much of the Black Eyed Peas’ fifth studio album, The E.N.D., was recorded in 2006. And its vocally-manipulated spoken-word hidden intro could easily be seen as an epigraph for the 2006-07 Bucks: “Everything around you is changing. Nothing stays the same. This version of myself is not permanent. Tomorrow I will be different. The energy never dies.” After all, the 2006-07 Bucks were changed.

In June, Ford was traded to the Toronto Raptors for Charlie Villanueva. In July, Magloire was traded to the Portland Trail Blazers for Steve Blake, Ha Seung-Jin, and Brian Skinner. In August, Smith was traded to the Denver Nuggets for Ruben Patterson, while Jiří Welsch left the Bucks for Spanish ACB league club Unicaja Málaga. Then, in September, Toni Kukoč retired.

But the most devastating change happened in October. Simmons suffered an ankle injury in training camp and, in December, the Bucks announced that he’d undergone “successful arthroscopic surgery [and was] expected to be sidelined for the rest of the regular season.” With it, the energy did die.

New recruit Villanueva was limited to 39 games, Redd played just 53, and the Bucks finished the season 14th in the Eastern Conference with a 28-54 record. In June’s NBA Draft, they controversially used the sixth overall pick to select Yi Jianlian out of China.

Simmons returned in 2007-08, mostly in a reserve role, putting up 7.6 PPG, 3.2 RPG, and 1.1 APG. But the winning didn’t—the Bucks finished just 26-56. Then, on June 26, less than three years after inking his 5-year $47m deal, Simmons was traded along with Yi to the Nets for Richard Jefferson. And, just like that, the Bobby Simmons era in Milwaukee was done.

By that time, high school had finished for my best mate and me.

Our adolescence had too.

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