Two teams changed the trajectory of their future in the 1998 NBA Draft. The Milwaukee Bucks traded their sixth overall pick, Robert Traylor for the Dallas Mavericks’ ninth pick, Dirk Nowitzki.

Looking back at that trade from today’s perspective, it was Dallas that clearly won that deal. This left former Bucks shooting guard Ray Allen wondering about the “what if” of that historic trade.

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According to Allen, the Bucks may not be the perfect team for a foreign player like Nowitzki, who had to develop both physically and mentally in the NBA. However, Ray is confident that with him and Dirk leading the charge, the Bucks could’ve probably achieved the unthinkable.

“It’s like Darko Milicic going to Detroit,” Allen said of Nowitzki going to Milwaukee. “He had too much pressure on him going to a good team. Maybe that happens with Dirk if he winds up with us in Milwaukee. So, maybe he would be great and we would win a championship, but maybe things would turn out a lot different.”

Ray believed Dirk was meant for Dallas, though

Taking a quick trip down memory lane, the Mavs were one of the worst teams in the league when they traded for Nowitzki in ’98. On the other hand, the Bucks were already getting the hang of it in the East and were winning more games than the Mavs.

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The way Allen saw it, the Nowitzki situation could have gone either way. However, Ray-Ray speculated that Dirk wouldn’t be given the time and space he needed to hone his game with the Bucks.

Moreover, playing time would’ve also been a problem for Nowitzki as Glenn Robinson, the Bucks’ starting small forward, was averaging more than 20 points a game. Moving Dirk to the power forward position wouldn’t be a smart move, as well, because Milwaukee had just gotten All-Star power forward Tyrone Hill at the time.

Looking back at it, Allen believes that it would’ve been interesting to see how he and Nowitzki would’ve performed as teammates. Yet, it was also evident that Dirk was a better fit for the Mavs.

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“I would have liked to have found out how we would have done with him,” Ray added. “I know that.”

“That’s a coulda-woulda-shoulda scenario,” he assessed. “I would like to know what would happen if he’d gone to Milwaukee. Him going to Dallas, though, you have to remember, it did give him the freedom to find his own way. What if he had gone to Milwaukee and it didn’t work out for him?”

What Dirk had to say about Milwaukee

As it turns out, Nowitzki also thought about what if the Bucks hadn’t traded him back then. For Dirk, it’s hard to imagine how things would’ve played out on the court, but he was certain he would’ve enjoyed what the city had to offer.

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“I think Milwaukee would have been great,” Nowitzki once said. “A lot of bratwursts, I think Milwaukee would have been fun. Being in Dallas, I enjoyed my time. It’s my new home. I still live there. It ended up working out for me. But I think Milwaukee would have been fun.”

As far as Nowitzki could tell, being traded to the Mavs was one of the best things that had happened in his life. He won an MVP and a championship there and he spent his entire career in Dallas.

This story was originally published by Basketball Network on Feb 21, 2026, where it first appeared in the Old School section. Add Basketball Network as a Preferred Source by clicking here.