The Milwaukee Bucks are no strangers to going all-in at the trade deadline. In recent years, they’ve repeatedly mortgaged draft picks and young talent for veterans billed as “win-now” pieces. But as the team approaches another trade deadline, it’s worth asking: can they afford to repeat this cycle?
The answer, increasingly, feels like a resounding no among the Bucks faithful. Gone are the days of "letting Horst cook" or what have you. When the Bucks are this strapped for cash and trade pieces, and with an Eastern Conference playoff race shaping up to be the most competitive it's been in years, the pressure is on for what their next move might be.
A cursory look at this team's trade history shows us that the front office just hasn't been the most forward-looking in this regard. Look no further than the acquisitions of Serge Ibaka, Jae Crowder and Pat Beverley—moves designed to bolster championship aspirations but which failed to deliver any significant impact.
The Bucks should have learned their lessons from past trade deadlines
Ibaka hardly played for the team and eventually made more noise off the court rather than on it. Crowder contributed briefly but disappeared when the stakes were highest. Beverley looked good for the Bucks when he suited up, but his age meant it didn't make sense to re-sign him later on.
And look at what it took to acquire them. Donte DiVincenzo thrived on the Golden State Warriors and then again on the New York Knicks. Jordan Nwora was a rotational player on the Toronto Raptors and the Indiana Pacers for a time. Cam Payne is still on the Knicks averaging seven points and three assists on 39.8 shooting from distance.
Meanwhile, all three veterans are out of the league, save for Crowder, who has yet to carve out a meaningful role on the Sacramento Kings after going unsigned in free agency.
Each of these deals came with a cost: young players who could have grown into contributors or draft picks that could have helped replenish an aging core in its later years closer to 2030.
The one time it did work out with PJ Tucker, the Bucks managed to blunder it once again by failing to re-sign their championship-winning forward. Tucker has gone on record saying he felt disrespected by the front office's approach to their initial talks.
While Giannis Antetokounmpo and Damian Lillard keep Milwaukee’s title window open, relying on patchwork solutions and undrafted free-agent signings may no longer be sustainable.
Milwaukee can't keep targeting veterans who aren't staying long
This year’s trade deadline presents an opportunity for the Bucks to pivot toward a more balanced approach. It seems as though they're keeping things under wraps this time around, but one can only hope they've shifted their former approach somewhat.
Rather than chasing another aging veteran who might not fit long-term, Milwaukee could target younger, more versatile players who align with their timeline and have room to grow. The league is full of promising players in need of a change of scenery, and the Bucks are one of the NBA’s best at developing talent once they’re in the fold lately. It's clear they know what they're looking for, but the hope is that they also know where to look.
With an eye on the future, the Bucks can make moves that not only enhance their title odds this season but also ensure their viability beyond it. Another short-sighted trade could push them further into a corner—one where their championship aspirations and their flexibility both vanish.
It’s time for Milwaukee to think bigger, smarter and younger. With their relative lack of assets these days, the stakes are simply too high to gamble on another quick fix.
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