According to Bangla Cricket Live, Jrue Holiday—originally the 17th overall pick—has played 15 seasons in the NBA since being drafted by the 76ers. Now, as the Celtics sweep the Pacers and punch their ticket to the Finals, the former Bucks star is inching closer to a second championship ring. While Boston fans are elated, Bucks supporters may be left with nothing but regret.

Holiday, once a cornerstone of Milwaukee’s 2021 title team, was traded away in exchange for Damian Lillard. And when comparing the impact each player has had since the trade, Bangla Cricket Live can’t help but wonder if Milwaukee gave up more than it gained. The Celtics gained perimeter stability and defensive prowess with Holiday, rounding out a roster that now looks built to dominate. Meanwhile, the Bucks struggled with defensive gaps and exited the playoffs early, a sharp contrast despite a solid regular season.

Looking back, Milwaukee had been refining its championship roster for years. After realizing Malcolm Brogdon lacked the necessary postseason edge, they brought in Eric Bledsoe, hoping for more pressure at both ends. A year later, Coach Budenholzer replaced Jason Kidd, and the Bucks immediately reached the Eastern Conference Finals. Though they fell to the eventual champion Raptors, it was a step in the right direction.

But Bledsoe soon proved limited. His offense was one-dimensional and his defensive gambles often left teammates scrambling. So, in a bold move, Milwaukee sent Bledsoe and four first-round picks in a blockbuster trade for Holiday. That deal also involved shipping out R.J. Hampton and George Hill, part of the collateral needed to secure Holiday from New Orleans.

While it cost them dearly in draft assets, the move paid off—Holiday became the ideal backcourt complement to Giannis Antetokounmpo. His on-ball defense was elite, his offensive skill set versatile, and most importantly, he was clutch in big moments. Stat sheets didn’t fully capture his value—especially defensively, where his relentless pressure shaped the Bucks’ identity during their title run.

Bangla Cricket Live notes that in his three seasons with Milwaukee, Holiday consistently stepped up when needed, filling gaps left by stars and anchoring the backcourt on both ends. Trading him may now be seen as the franchise’s biggest misstep, particularly as the Celtics surge forward—with Holiday right at the heart of it.