How the 1986-87 Milwaukee Bucks Fought Through Adversity, Depth Challenges, and Boston Heartbreak to Nearly Topple the Eastern Conference Giants

The 1986–87 Milwaukee Bucks season remains one of the most compelling and underrated campaigns in the franchise’s rich history. Spearheaded by head coach Don Nelson—renowned for his creativity and player-friendly schemes—the Bucks fielded a balanced, tough-minded squad headlined by All-Star forward Terry Cummings and defensive maestro Paul Pressey. Despite roster turnover, injuries, and the Eastern Conference gauntlet that featured the dynastic Boston Celtics, Milwaukee clawed its way to a 50-32 record and came within one win of upsetting the top-seeded Celtics in the Eastern Conference Semifinals.

Milwaukee’s season began under the radar, but the team’s blueprint was clear. John Lucas, the veteran point guard who joined midseason in January, brought leadership and passing savvy to an already fluid offense. Sidney Moncrief, still resilient despite dealing with persistent knee issues, provided a veteran presence and leadership that couldn’t be measured in a box score. Paul Pressey, the prototype for the “point forward” role, orchestrated the offense with precision while locking down opponents’ best perimeter threats nightly. His averages of 7.2 assists and 1.8 steals per game led the team, and his impact landed him a deserved spot on the NBA All-Defensive Second Team.

Terry Cummings was the offensive engine, delivering a team-best 20.8 points per game during the regular season and ratcheting that up to 22.3 in the playoffs. His midrange mastery, rebounding toughness, and quickness in the post made him a matchup nightmare for opposing forwards. Stretching the floor and controlling the boards was veteran big man Jack Sikma, who added 10.0 rebounds and 1.1 blocks per game, serving as the Bucks’ interior anchor and emotional core.

Despite these stars, Milwaukee’s depth proved equally critical. Ricky Pierce’s explosive scoring off the bench earned him NBA Sixth Man of the Year honors, and rightly so. Pierce could swing games with a sudden scoring burst, making him a perfect complement to Pressey’s pass-first tendencies. Add in the sharp-shooting Craig Hodges, future NBA head coach Scott Skiles, and the ever-reliable Junior Bridgeman, and Nelson had a capable second unit that could hold leads or change momentum when starters rested.

Yet, Milwaukee’s season was anything but smooth. Early-season roster instability saw players like Kenny Fields and Mike Glenn waived, while Chris Engler was traded to Portland in exchange for a future second-round pick. The Bucks’ front office worked to stabilize the bench, signing veteran defenders like Dudley Bradley in October and Junior Bridgeman in January. Later additions like John Lucas and Jerome Henderson provided the right mix of experience and energy as the playoff race heated up.

Even with a strong core, Milwaukee faced adversity all season long. The Eastern Conference was stacked—Larry Bird’s Celtics were still in full force, the young Detroit Pistons were emerging with the Bad Boy identity, and the Chicago Bulls had just seen the arrival of a certain Michael Jordan. The Bucks weathered the storm and finished with a 50-32 record, earning the No. 4 seed in the Eastern Conference.

Their first-round playoff matchup against the Philadelphia 76ers proved to be an epic. With Charles Barkley and Maurice Cheeks leading Philly, the Bucks found themselves in a five-game war. Cummings, Sikma, and Pressey delivered consistently, while Moncrief’s clutch shot-making and Pierce’s bench scoring proved decisive. The Bucks escaped with a 3-2 series win, setting up a much-anticipated showdown with the top-seeded Celtics.

What followed in the Eastern Semifinals was a battle that tested Milwaukee’s resolve to its core. Boston had homecourt advantage and the aura of champions, but the Bucks refused to fold. With Don Nelson’s coaching wizardry on full display, Milwaukee slowed the tempo, spread the floor, and leaned heavily on its defensive principles. Pressey averaged 8.6 assists and 2.3 steals per game during the series, becoming a two-way force the Celtics struggled to contain. Sikma continued his dominance on the glass, and Cummings played inspired basketball, going head-to-head with Boston’s rugged frontcourt.

The series extended to seven grueling games. Game 7 in Boston Garden was a classic, with the Bucks staying close until the final minutes. Despite their heroic efforts, Milwaukee ultimately fell 119–113, ending their season just shy of the Eastern Conference Finals. It was a heartbreaking loss, but one that etched this team’s grit and heart into Bucks lore.

Off the court, this season also marked a pivotal period in Don Nelson’s long tenure. Known for his willingness to adapt, Nelson frequently shuffled lineups and adjusted roles. He transformed Paul Pressey into one of the league’s most unique players—an oversized playmaker capable of guarding multiple positions and running the offense. Nelson’s “point forward” innovation would go on to influence generations of basketball, with Pressey often cited as a pioneer of the position.

Behind the scenes, the Bucks also saw the arrival of second-round draft pick Keith Smith, a 6’0″ guard out of Loyola Chicago. While Smith didn’t log major minutes, his development was part of Milwaukee’s long-term planning. Meanwhile, players like Randy Breuer and Paul Mokeski provided size and physicality off the bench, often used to counteract bigger lineups in the Eastern Conference.

There was also an emotional component to the year. Junior Bridgeman’s return brought nostalgia and leadership—having been a key piece of Milwaukee’s strong 1980s teams before leaving in a trade, his January signing was celebrated by fans and teammates alike. John Lucas, who had battled personal demons and overcome addiction, became a locker room inspiration. His story of redemption and his reliable play at the point guard position helped galvanize the team during its playoff run.

As the season concluded, Milwaukee stood as a franchise at a crossroads. The Celtics dynasty was aging, the Bulls and Pistons were rising, and the Bucks—though consistently excellent—were caught in the middle. Yet the 1986–87 squad proved that with the right mix of stars, savvy coaching, and selfless depth, they could contend with anyone.

Their seven-game series against Boston remains one of the most thrilling playoff matchups in franchise history—a true David vs. Goliath story where Milwaukee very nearly toppled the NBA’s reigning powerhouse. Paul Pressey’s vision and defense, Terry Cummings’ scoring and leadership, Jack Sikma’s inside toughness, and Ricky Pierce’s electric bench production created a team that was equal parts graceful and gritty.

Although they didn’t hoist a championship banner, the legacy of the 1986–87 Milwaukee Bucks lives on. They were a blueprint of resilience, a product of brilliant coaching, and a team that left everything on the hardwood. For Bucks fans, that season is remembered not just for how close they came—but for how valiantly they fought, and how loudly they announced their place among the elite.