In the 1980s, there had been changes in the Ownership and arena changes.
They would be playing in the smallest arena in the league and a Milwaukee businessman named Herb Kohl bought the Milwaukee Bucks. Before the deal, the Bradley Center was donated by Jane and Lloyd Pettit.
In the 1990s, the Bucks just remained as a mediocre team. They were headed by several coaches such as Frank Hamblen, Mike Dunleavy and Chris Ford. Starting from 1991 until 1998, the Bucks had seven straight seasons with losing records. In this era, they had Glenn Robinson as the first overall pick in the 1994 NBA Draft and acquired Ray Allen in 1996 draft from the Minnesota Timberwolves.
The Bucks signed George Karl in 1998 and with the addition of other talented players like Tim Thomas and Sam Cassell, the Bucks would rise to become one of the top teams in the Eastern Conference. The Bucks would win 52 games in 2001 season and they would also win the Central Division title. In the playoffs, the Bucks advanced through the 2001 Eastern Conference Finals but eliminated by the Philadelphia 76ers in seven games.
They acquired high-flyer Anthony Mason at the start of the 2001-02 season. Acquiring Mason, the Bucks seems to be the team to beat in the season. But with the presence of Mason, the team’s chemistry in or off the court has struggled and destroyed.
They were the fourth seed in the midpoint of the season of the Eastern Conference but later on be eliminated from the Playoff contention. There was a tension between the three stars of the team and with the coach that would result to a trade of Glenn Robinson to Atlanta Hawks for Toni Kukoc and a first round pick.
In 2002-03 season, Ray Allen and Flip Murray was traded to the Seattle Supersonics in exchange for Gary Payton and Desmond Mason. It opened the opportunity for Michael Redd to play more minutes and with the leadership of Gary Payton they finished the season with 42-40 record. They advanced in the playoffs but eliminated immediately by the New Jersey Nets.
Starting from 2003 to 2008, the Bucks were just struggling and had been redesigning their team with numerous trades and acquisition. In 2005, they acquired Andrew Bogut as the number 1 pick of the draft. Bogut has struggled with injuries but later on be a key player for them contributing more in points, rebounds and blocks.
In 2009, they acquired the famous flashy player Brandon Jennings. They also acquired John Salmons in the season. With Salmons, Jennings and an improved Bogut and Ilyasova leading the team, they became a playoff contender finishing with a 46-36 record.