The Milwaukee Bucks, considered a small-market team, are not typically a favored choice for top free agents. However, this hasn’t hindered their success in winning titles, as they proudly hold two NBA championships, the latest in 2021.
Throughout the 2020s, they have emerged as one of the decade’s top teams by strategically enhancing their roster through astute free agency acquisitions. Here’s a look at the Bucks’ top five signings in free agency of all time.
5Pat Connaughton (2018)
Contract: 2-years, $3.3 million
During the 2018 Free Agency, the Bucks signed Pat Connaughton to enhance their shooting, seizing the opportunity after the Portland Trail Blazers opted not to retain him. This decision completed a circle for Connaughton, who had been initially drafted by the Brooklyn Nets in 2015 via a Bucks pick.
Connaughton faced challenges initially with his shooting in Milwaukee, shooting only 33 percent from three-point range over his first two seasons. However, his energetic play, particularly his hustle on rebounds, impressed the team enough to secure him a three-year contract extension valued at $16 million.
| Pat Connaughton – Milwaukee Bucks Stats | |
|---|---|
| Category | Stat |
| PPG | 7.0 |
| RPG | 4.2 |
| FG% | 43.9% |
| 3PT% | 35.7% |
During the 2020-21 season, as the Bucks approached their championship run, Connaughton made significant contributions. After shooting 37 percent from three-point range in the regular season, he elevated his performance to 38 percent in the playoffs. In the Finals, his impact intensified, averaging 9.2 points and 5.8 rebounds per game while shooting an impressive 44.1 percent from beyond the arc, aiding the Bucks in securing their first NBA title in half a century.
Following this success, Connaughton rightfully earned a contract extension, signing a three-year deal valued at $30 million. His contract extends through the 2025-26 season, with a player option set at $9.2 million.
4Greg Monroe (2015)
Contract: 3-years, $50 million
It was unprecedented for free agents to choose the Milwaukee Bucks over the Los Angeles Lakers and the New York Knicks until Greg Monroe broke that trend in 2015. He signed a maximum contract with the Bucks, matching the offers from those other teams, marking him as arguably their most significant marquee free agent acquisition.
However, Monroe struggled to mesh with the Bucks’ youthful core at the time, which included Giannis Antetokounmpo, Khris Middleton, and Jabari Parker. Within a year, he transitioned to a bench role with the Bucks, a position that suited him better in Milwaukee. He made a notable impact, even contending for the Sixth Man of the Year award by averaging 11.6 points and 6.6 rebounds per game during the 2016-17 season.
| Greg Monroe – Milwaukee Bucks Stats | |
|---|---|
| Category | Stat |
| PPG | 13.1 |
| RPG | 7.5 |
| APG | 2.2 |
| SPG | 1.0 |
| FG% | 52.6% |
However, small-market teams face constraints when it comes to spending on bench players, which ultimately led to Monroe being traded. By the middle of his third season with the Bucks, they dealt him to the Trail Blazers in exchange for Eric Bledsoe. Although Monroe briefly returned to Milwaukee on a 10-day contract in February 2022, that marked his final appearance in a Bucks uniform.
Following his time in the NBA, Monroe played in China and Puerto Rico before signing a contract with the Big 3 in April 2024, just ahead of the league’s seventh season.
3Mo Williams (2004)
Contract: 3 years, $5.2 million
Mo Williams started his NBA journey with the Utah Jazz, drafted in the second round. He moved to the Bucks in his second season after signing an offer sheet that the Jazz decided not to match. Unlike high-profile signings such as Monroe, Williams, a standout from Alabama, left a notable mark during the Bucks’ challenging period in the early 2000s.
He quickly endeared himself to fans, especially memorable was a regular-season game against the Pacers in 2005. Williams spearheaded the Bucks’ comeback from a 14-point deficit and clinched the victory with a buzzer-beating game-winner.
| Mo Williams – Milwaukee Bucks Stats | |
|---|---|
| Category | Stat |
| PPG | 14.1 |
| RPG | 3.5 |
| APG | 5.7 |
| SPG | 1.1 |
| FG% | 45.0% |
| 3PT% | 36.4% |
After the Bucks traded TJ Ford, Mo Williams stepped into a full-time starting role and flourished. His statistics improved significantly, rising from 12.1 points and 4.0 assists per game to 17.3 points and 6.1 assists per game during the 2006-07 season. As a result, the Bucks rewarded him with a six-year, $51.5 million contract extension.
Despite maintaining similar statistical performance with improved efficiency in his fourth season, the Bucks traded Williams to the Cleveland Cavaliers after the 2007-08 season. He went on to play for several teams before retiring with the Cavaliers in 2017.
2Bobby Portis (2020)
Contract: 2 years, $7.4 million
Bobby Portis joined the Bucks in 2020, expressing a desire to be part of a “winning culture” that he believed was lacking with the Knicks. Prior to his arrival, the Bucks had secured the top seed in consecutive seasons but had struggled in the playoffs.
Initially serving as a bench player in Milwaukee, Portis provided valuable contributions on both the boards and with his impressive shooting prowess. He achieved career-best efficiency in his first season with the Bucks, shooting 52.3 percent from the field and 47.1 percent from three-point range.
While his shooting percentages dipped slightly in the postseason, Portis’ energetic play off the bench proved pivotal as the Bucks clinched the 2021 NBA championship.
| Bobby Portis – Milwaukee Bucks Stats | |
|---|---|
| Category | Stat |
| PPG | 13.5 |
| RPG | 8.3 |
| FG% | 50.0% |
| 3PT% | 40.3% |
During the Eastern Conference Finals, Portis stepped into the starting lineup for two games when Antetokounmpo was sidelined, seamlessly fulfilling his role and aiding the Bucks in securing the series. Following this inspiring performance, Portis has endeared himself to Milwaukee fans and become a beloved figure in the city.
During the off-season, Portis agreed to a fresh two-year contract valued at $9 million, with a player option for the second year. As anticipated, he maintained his strong performance, leading to a substantial raise in 2022 when he signed a four-year contract worth $49 million. His current commitment with the Bucks runs until the 2025-26 season, with a player option for that year.
1Brook Lopez (2018)
Contract: 1 year, $3.3 million
In the 2018 Free Agency, the Lakers opted not to retain Brook Lopez after just one season, prompting the Bucks to seize the opportunity by signing him using their bi-annual exception. This move provided Lopez a chance to rejuvenate his career following a challenging season in LA.
Lopez quickly established himself in Milwaukee, securing the starting center position previously held by John Henson, who had fallen short of expectations. Despite concerns about his rebounding on a Bucks team that ranked last in the league in rebounds during the 2017-18 season, Lopez mitigated this with his effective box-out techniques. Since reinventing his game in 2016, known affectionately as “Splash Mountain,” Lopez has been a consistent threat from beyond the arc, a crucial asset for the Bucks’ offensive strategy.
| Brook Lopez – Milwaukee Bucks Stats | |
|---|---|
| Category | Stat |
| PPG | 13.0 |
| RPG | 5.2 |
| BPG | 2.2 |
| FG% | 48.2% |
| 3PT% | 35.4% |
In Lopez’s debut season with the Bucks, the team achieved 60 victories, during which he averaged a career-best 2.2 blocks per game. These contributions led to him signing a four-year, $52 million contract the following year. Lopez continued to elevate his defensive prowess, earning his first All-Defensive team selection in 2020. His impact was crucial in the Bucks’ 2021 championship triumph, as he started every game and served as a cornerstone of their defense.
Following his second-place finish in the Defensive Player of the Year voting in 2023, Lopez secured a substantial two-year contract valued at $48 million to remain with the Bucks. He is set to enter the final year of this deal during the 2024-25 season.
