Wondering whether 10 years of helping kids stay off the streets and on a basketball court or football field was enough.
Doubting whether all the tutoring and feeding of disadvantaged kids and fundraising for them was enough.
Fearing that if he didn't do more, more kids would end up in caskets, as Jaykwon did.
Then, when he thought the night couldn't get worse, he received a Facebook message from a parent who had been nothing but a headache in the past.
"I couldn't believe it, but the message was telling me how much we had done for their kid and what a difference we had made in the kid's life," Whitlow said. "The timing of that message was everything. It wasn't going to bring Jaykwon back, but it reminded me of the hope we give these kids."
Whitlow and his wife, Maree, are president and treasurer, respectively, of a Groveport-based nonprofit organization called Columbus ICE - short for Inspiring Children to Excellence, a reference to its work in youth sports, the classroom and beyond.
The Whitlows' inspiration for the program came after watching the 2008 LeBron James documentary "More Than A Game," which chronicles the rise of young athletes from the inner city. Michael started by creating an Amateur Athletic Union boys basketball team in 2009, and it grew quickly and officially was established as the nonprofit Columbus ICE in 2011.
ICE has about 225 boys and girls, ranging in age from 4 to 14, in its football, basketball and cheerleading programs.
It takes at least $75,000 a year to pay for the equipment, travel and other program expenses. The Whitlows have had some success in winning grants through foundations, but much of the nonprofit's revenue is from year-round fundraising that includes carwashes, sales of baked goods, and partnerships with local bingo halls. There are 30 coaches and 10 team moms for just the five football teams, plus six cheerleading coaches and four basketball coaches. And all are volunteers.
But the program is far more than sports and competition. It has to be.
Many of the kids come from poor, single-parent homes or are being raised by other relatives because their parents are incarcerated or aren't part of their lives.
When there is trouble at school, teachers sometimes call the ICE coaches because the kids know there will be consequences: They won't be allowed to practice or play unless they can show proof that their grades and behavior are good.
Michael and Maree spend hundreds of hours tutoring the children at their home in math, English and other subjects. And that's between Michael's jobs as a real estate agent and high school football coach at Groveport Madison High School, Maree's job as a senior human resources director, and the couple's efforts to help to guide their three adult kids, who are in their 20s. Michael has also has been battling Crohn's disease for a decade and drives to the Cleveland Clinic regularly for treatment.
Maree sighed when asked how they juggle it all, then paused.
The program received little citywide attention until that night in late May when authorities say that Jaykwon, who played for one of the ICE football teams, was shot by a 13-year-old boy and died about an hour later in Mount Carmel East hospital.
Maree has struggled with the memory of seeing Jaykwon dressed in a grown man's suit in an open casket when she attended the funeral service.
"I saw his mother's pain, and I want to make sure that no other parent has to endure that," Maree said. "We love these kids; they know they can count on us. I walk out on the practice fields, and they yell, 'Hey, Miss Maree!' and then they tell me about their day. That's the sense of belonging we want to give them."
Michael walked back to the lunch table at a Mexican restaurant in early June with a sheepish grin and told his wife that their house was about to get a little more crowded.
"I'm sorry, Maree, but they have nowhere else to go," Michael said.
Alyssa Morris was stranded at a cheap motel with her five young children, all involved in the ICE program. The 35-year-old single mother had lost her apartment in Columbus, then had to leave her sister's home in Cleveland due to a domestic situation, and was back in town.
Michael was already trying to raise money for Morris to find proper housing, but he was now offering to open his home to her family for as long as they needed it.
Morris' 9-year-old son, Drayton, is one of the stars of the ICE football program. With his speed and agility, almost every youth football team in the area would covet him as its running back. But Alyssa knows that Michael and Maree aren't using her son to win football games.
"They have been helping me raise my children the past couple of years," Morris said. "It's been a scary time for me, having no place to go, and I don't know what we would do without them. I want them (her children) all to make it to college someday, and without this, they wouldn't have a chance."
A few weeks ago, Michael kept his promise and helped Morris and her children find a place to live on the South Side.
LaQwanda Walker had the same dreams for her son, Jaykwon, until he was fatally shot near Sherwood Middle School, where he was a student.
Jaykwon played football in the ICE program for three years, and his mom and coaches said they witnessed a transformation. He came into the program stubborn and defiant. When he would get into trouble at school, it was the coaches who would pick him up from the office and hold him accountable, Walker said. Eventually, he became one of the leaders who used his lovable, infectious, positive attitude to inspire the other kids.
They helped inspire him to become a graduate of the Columbus police Teen and Police Service Academy, or TAPS, a program in which students partner with police mentors. It made Jaykwon protective of his neighborhood, friends and family.
"I watched Bobby totally change. I've never had a kid like him," said Terry Johnson, one of Jaykwon's football coaches. "These boys are like my sons, and it hurt so much that we lost one."
Walker said she will be eternally grateful to the Whitlows and all the other mentors who helped Jaykwon.
"They were role models for my son," Walker said. "Nothing can bring my boy back, but I hope people hear about what happened to my son, and they make sure their child is getting guidance or help showing their kids the right path."
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