Portland Trail Blazers (2015–2018) Connaughton was drafted with the 41st pick by the
Brooklyn Nets in the
2015 NBA draft. His draft rights, along with
Mason Plumlee, were then traded to the
Portland Trail Blazers for
Steve Blake and the draft rights to the 23rd pick in the draft,
Rondae Hollis-Jefferson. He signed a three-year deal with the Trail Blazers on July 9. The first two years of the contract were guaranteed, with the stipulation that Connaughton would not be allowed to play professional baseball during that timespan. He made his debut for the Trail Blazers on October 30, 2015, scoring five points in a loss to the
Phoenix Suns. He appeared in 34 games for the Trail Blazers as a rookie. On April 13, 2017, in the Blazers' 2016–17 season finale, Connaughton scored a then career-high 19 points in a 103–100 loss to the
New Orleans Pelicans. In the Trail Blazers' 2017–18 season opener on October 18, 2017, Connaughton scored a then career-high 24 points while making 4 of 6 3-pointers in a 124–76 win over the
Phoenix Suns.
Milwaukee Bucks (2018–2025) On August 1, 2018, Connaughton signed with the
Milwaukee Bucks. He competed in the
Slam Dunk Contest at the
2020 NBA All-Star Game, dunking over
Milwaukee Brewers outfielder
Christian Yelich and finishing third in the tournament. On August 20, 2020, Connaughton scored 15 points and grabbed 11 rebounds in a 111–96 Game 2 win during the Bucks' first round postseason matchup against the
Orlando Magic. Connaughton won his first NBA championship on July 20, 2021, averaging 9.2 points per game and 5.8 rebounds per game while shooting 44.1% from three-point range in six games in the NBA Finals as the Bucks defeated the
Phoenix Suns. On November 10, 2021, Connaughton scored a season-high 23 points and made a career-high seven three-point shots during a 112–100 win over the
New York Knicks. On February 14, 2022, he underwent right hand surgery and was ruled out for at least a month. On April 27, during the first round of the
2022 NBA Playoffs, Connaughton scored 20 points in just 23 minutes of playing time in a decisive 116–100 Game 5 win over the
Chicago Bulls. On June 22, 2022, Connaughton opted into his $5.7M player option to remain with the Bucks. Later, on July 13, 2022, Connaughton signed a three-year, $28.5M extension with the Bucks. On January 26, 2023, Connaughton scored 19 points and recorded a season-high 12 rebounds during a 107–99 win over the
Denver Nuggets. On April 13, 2025, Connaughton scored a career-high 43 points in a 140–133 win over the
Detroit Pistons.
Charlotte Hornets (2025–present) On July 6, 2025, Connaughton was traded to the
Charlotte Hornets alongside two second-round picks in exchange for
Vasilije Micić. On February 4, 2026, Connaughton was waived by the Hornets. However, he was re-signed by the team on February 9. ==Career statistics==