UConn alumna makes a dream come true at high school graduation

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Grace Merritt

2 min read

Calibe Simpson, a Jamaican immigrant who struggled with homelessness, got the surprise of her life at her high school graduation in Hartford last week.

The commencement speaker, UConn alumna Trisha Bailey ’99 (CLAS), called her up on stage and announced that she was going to cover a significant portion of her costs to go to UConn.

“I was so surprised I started crying,” Simpson said after the ceremony at Weaver High School. “This is a dream come true for both me and my family. Until today, I did not know where I would get the money to pay for college.”

Bailey’s generous support over the next four years will supplement the financial aid UConn is providing. Bailey, a Jamaican-born philanthropist and successful entrepreneur, says she saw herself in Simpson and was moved by her story.

“UConn gave me my first chance,” Bailey says. “Now, in collaboration with UConn, we’re going to give Calibe her first chance at success.”

Simpson grew up in an extremely poor area of Jamaica. She was raised by a single mother, who tried mightily to support Simpson and her younger brother but often struggled to put food on the table.

When Simpson was invited to come to the United States two years ago to live with her aunt in Hartford, she jumped at the chance. She enrolled in Weaver and quickly got involved, playing three sports, becoming class president, and working part-time at a local restaurant. But her housing arrangement fell apart and she suddenly found herself homeless. Weaver and DCF officials stepped in to help her find a new legal guardian.

As she got ready to graduate this spring, she applied to and got into more than 15 colleges with UConn as her top choice. But she had no idea how she’d pay for college.

A teacher saw Simpson’s potential and reached out to Bailey. The teacher had been friends with Bailey since they had gone to Weaver together. She knew that Bailey provides scholarships to hundreds of students in her home state of Florida.

“I told her that I see something in this young woman,” the teacher, Colette Daye ’00 (CLAS), says. “Calibe has a big heart. She has nothing, but she is always trying to help someone. She tries to give to others who don’t have anything. I’ve listened to her encourage her classmates to apply for college. I was just so impressed with her.”

When Bailey heard Simpson’s story, she decided to surprise her at graduation.

“I saw myself in this young girl,” Bailey explains. “I grew up in Jamaica and I was pretty much below the poverty line. I’m impressed that she’s excelled so well in her studies despite all her challenges outside of school. What touched my heart more than anything else was her kindness, and how she is always helping everyone else. Her level of kindness resonates with me because that’s who I am and that’s the type of people I want to support.”

Simpson says Bailey’s generosity has changed her life.

“I’m going to be able to go on and get my degree,” Simpson says. “It’s going to help me build my career. I know I’m going to work hard and I’m going to make her proud. It’s a dream come true.”

Bailey is a highly successful entrepreneur who founded several medical equipment and real estate companies. Her autobiography, “Unbroken,” is due out in July. While at UConn, she was a student-athlete on UConn’s cross-country and track and field teams. A proud alum, she recently committed a major lead gift to build the Bailey Student Athlete Success Center on the Storrs campus.


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