Born on 5 June 1991, to a Danish mother and an American father, he began to test his football skills at a local club, SGI after which he moved to Esbjerg.
His versatility and playmaking skills helped him secure a move to Danish club FC Midtylland at age 15. Injuries forced him back to his former club Esbjerg, where he penned a three-year youth contract in 2007.
After trial spells at Reggina and Newcastle United, he finally made his debut for his home club Esbjerg FB under the guidance of coach Jess Thorup. Under the new manager, he became a key figure for the team, featuring in every single game.
The 2012/2013 ended with him scoring 12 times in all competitions. After he grabbed a brace in the semi-finals of the Danish Cup, he provided an assist for Youseff Toutouh for what would be the goal that gave them their first Danish Cup title in 43 years. Esbjerg also finished 5th place in the league that season.
Amidst interests from clubs like Auxerre, Rennes, Celtic, and Hull City, Braithwaite signed for Toulouse in a move worth £2 million. In his 4 year stay at the club, he played 163 games in all competitions and scored 44 times. In the summer of 2017, Middlesbrough signed him for £9 million.
After playing a couple of games for the team in the first half of the season, he was loaned out to French club Bordeaux for the remainder of the season.
On his return to Boro in July 2018, he expressed his interests to leave the club on loan in Spain. The club reluctantly obliged to his request and was loaned to Leganes in January 2019.
In the summer of July 2019, Braithwaite completed a permanent move to Leganes for a rumoured fee of €5 million - the second most expensive player in the Leganes's history.
July 2019 - June 2023
July 2019 - July 2019
January 2019 - June 2019
July 2018 - January 2019
January 2018 - June 2018
July 2017 - January 2018
August 2013 - July 2017
July 2009 - August 2013