shared a picture of his daughter and partner on July 11, 2019, after the Milwaukee Bucks re-signed his contract.
Two years after they welcomed their daughter, the couple had their second child, a boy, on July 21, 2021, at a local Milwaukee hospital. His birth happened hours after the Milwaukee Bucks defeated the Phoenix Suns.
With the arrival of his second child, Middleton had doubts about leaving his family to join Team USA at the Olympics in Tokyo, which started a few days later.
On Mother's day in 2020, he took to Instagram to wish Dutton a happy mother's day. In the caption of his post, he wrote:
"Happy Mother’s Day to this Mom and all the Moms out there! We are lucky to have you in our lives and thank you for everything you do!"
The 2020 Summer Olympics in Tokyo, Japan, began on July 24, 2021, and ended on August 8, 2021. With the start date being three days after his son was born, Middleton considered not going.
The athlete was torn because being a part of an Olympic team was one of his dreams for his professional career. In addition, becoming a father again was another dream.
The basketballer's dreams came true simultaneously, and he did not want to be away from them. He thought about giving up his Olympics dream for his family.
In an interview, Middleton, who starred as himself in Adam Sandler's sports drama "Hustle," revealed that Dutton encouraged him to play in the Olympics. She promised him everything would be fine when he returned.
He eventually joined Team USA at the Olympics and won a gold medal. In addition, he was among the few players to win Finals and gold medals in one summer.
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