Who Are the Parents of Rai Benjamin? Learn Everything About the Olympian’s Family

Rai Benjamin’s quest for Olympic gold started with a glass of water. Yes, that’s all it took his mother, Jeanette Mason, to recognize his athletic abilities. She remembers asking her son for water and watching him fly out and then in with a glass of it. In fact, by age two or three, he was already running!

We can think about this as a blessing today, but when Benjamin was a kid, his mother received several complaints about him being too active. “I honestly thought he had ADHD (attention deficit hyperactivity disorder) … I was always praying there’d be something he could put his energy into,” Mason once revealed. That’s how sports came into the picture. But none of this would be possible without Rai Benjamin’s parents recognizing his talents. Here’s all we know about his parents, who propelled him to success!

Were Rai Benjamin’s parents athletes?

Rai Benjamin, born on July 27, 1997, is a Bronx native, but his roots go all the way back to Antigua, thanks to his parents, Jeanette Mason and Winston Keithroy Matthew Benjamin.

His father was a professional cricket player. He was part of the West Indies squad that went undefeated for eight straight years. Winston played 21 test matches and 85 One-Day Internationals for the team (1986–1995). So Rai got a mix of NYC hustle and proud Caribbean heritage growing up.

In an interview with Men’s Health in June, Rai reflected on his upbringing, saying, “I’m fortunate enough just to have this be the focus and have a supportive family that understands that I’m not gonna talk to them every day. My family has always known sacrifice. My mom and dad know what it’s like to sacrifice and put things aside to be successful.”

His mother, however, was not an athlete and never played any sport. Yet, she had a keen eye on her son’s talents. “I don’t want to sound too haughty, but the first day of (athletic) registration at Mount Vernon High School, I said he was going to play sports in college,” she recalled. And she was right!

After two seasons at UCLA, he transferred to USC. He achieved several milestones there:

• In 2017, he came second and earned the All-America honors in the 400m hurdles with a PR of 48.33 at the NCAA Championships. Interestingly, he was just .01 seconds away from coming first. His time matched the USC school record set by two-time Olympic gold medalist Felix Sanchez in 2000.
• He also won the Pac-12 400m hurdles title in 2017.
• Rai Benjamin won the Dual Meet 400m hurdles title with a time of 54.58. He also came second in the 400m with a time of 45.72 (2017).
• Finished sixth at the NCAA Championships and earned the All-America honors (2016).

But all this didn’t come easy. He had to sacrifice some of his dreams. When he was at Mount Vernon, he was quite interested in football. But his coaches saw a different potential. Benjamin could run fast but didn’t have the build needed for football. Hence, the coaches convinced him to try track. He could run the 400 meters in 51 seconds back then.

Mount Vernon’s junior varsity football and head track coach, Marcus Green, was impressed. “If he stays in school and gets good grades, I’ll guarantee he’ll get a full (college) ride (in track),” he promised Jeanette Mason. In fact, Benjamin’s coaches were thankful that the mother allowed them to have an impact on her son.

She motivated him to excel in his academics so he could go to a great college and his coaches did their best to push his athletic skills. But what about his father?

How did the cricketer father influence his son, Rai Benjamin?

Growing up in New York, Rai gave cricket a shot, preferring batting over bowling, unlike his dad. Winston, now 59 and having played internationally from 1986 to 1995, excelled as a bowler but also boasted two centuries and 21 half-centuries in first-class cricket.

Despite Rai’s brief cricket stint, Winston didn’t mince words about his skills, once calling them “absolutely crappy.” But seeing the 2021 Tokyo Olympian sprint down the track brought immense joy to his dad. Rai’s “graceful and joyful” strides, as Winston shared with Olympics.com in 2021, made him feel younger.

Rai Benjamin’s path to becoming a two-time Olympian wasn’t straightforward. While he looked up to cricket legends like Brian Lara, he admitted it wasn’t his game. But things seem to have worked out for him in the long run.

But coming back to the father, after his playing career, Winston moved to coaching. He started with the Leeward Islands and stayed there until 2005. He now coaches at Clare Hall Secondary School in Antigua.

Rai Benjamin and Winston share more than athletic genes; they’ve had heart-to-heart talks about the highs and lows of elite sports. Reflecting on their bond, Winston shared in 2021, “We might have played different games, but there are things that are common in every sport, and he won’t commit the mistakes that I have in mine.”

He also shared that “If he wins a medal, Antigua will celebrate as much as America.”

With the 2024 Paris Olympics, fans are hopeful that Rai Benjamin’s dream of winning a medal will come true. What do you think about this tight-knit family and their passion for sports?