When a baseball player finds out only the day before that he is about to be promoted to the major leagues, family members and friends are often left scrambling to make travel arrangements to see their loved one’s debut first-hand.
Braden Montgomery’s family was tested more than most.
Monday afternoon, Richard Willock, Braden’s stepfather, left Jackson, Mississippi, with his youngest son, 17-year-old Mason, on a six-hour drive to Georgia, where Mason was scheduled to attend a baseball camp. It rained for much of the ride.
At around 7, with Mason about an hour into his first session, Richard’s phone rang. “He said, ‘Good news,’ ’’ Richard said, “and that’s when the fire drill started.’’
A special moment for Braden and his family 🤍 pic.twitter.com/5bNneMvrqz
— Chicago White Sox (@whitesox) June 11, 2026
Braden’s mom, Gretchen, was scheduled to work the overnight shift as an emergency physician at St. Dominic’s Hospital in Jackson. She was asleep when Braden called Richard. They chatted for about an hour, then called Gretchen to share the news. She still went to work, but swung into action, making flight plans, and arranging for someone to cover her shifts the next two nights.
Mason’s first session of camp ended at 9 that night. There would be no session for him the next day. “Guess what?’’ Richard told Mason, informing him of Braden’s callup. “We’re driving back to Jackson.’’
They arrived back in Mississippi around 3:30 a.m. and only had a short time to sleep before they had to catch an 8 a.m. flight. To get to Chicago, they connected in Charlotte, where Braden had been playing for the Triple-A Knights. “We could have picked him up,’’ Richard said with a laugh.
Braden’s older sister, Skylar, was in medical school at Case Western and would not be able to arrive until the next day. They had one unhappy passenger in their midst: Braden’s younger sister Marley.
“She was kind of a grump,’’ Richard said.
In fairness to Marley, she had a good reason: It was her 15th birthday, and this was not the first time big brother had stepped on her day. On her 13th birthday, Braden had fractured his ankle sliding into home plate while playing for Texas A&M in the NCAA Super Regionals.
All was forgotten by the time they gathered at the Rate on Tuesday night. Braden’s pass list was 32 names long. Richard said counting the friends who purchased tickets, they were 50 strong in all.
“Let me tell you about this dream I had last night…” Gretchen Montgomery posted on X.
Braden’s walkoff home run was not a dream. It was history. He became the fifth player ever to hit a walk-off home run in his big-league debut.
Watch the video Gretchen shot of the moment and posted on X.
“Oh my God, oh my God, oh my God, oh my God,’’ you can hear someone screaming in the background, as the Rate Field crowd erupted.
After it was over, and all the interviews were completed, Braden emerged from the clubhouse and joined his family on the field for hugs and photos. He’s a huge fan of deep-dish pizza.
“Let’s go to Uno’s,’’ said one of his agents, who called the restaurant and arranged for the kitchen to stay open after-hours.
There, Richard said, everyone exchanged their “disbelief stories.”
“I shouldn’t say everybody,’’ he said. “All these people, you know, are in disbelief. I’m sitting there watching them, listening to them. Like, ‘I’ve been telling y’all this.’ ’’
It was after midnight before they got back to their hotel. While most everyone else went upstairs, he said he stayed downstairs, chatting with friends.
Wednesday morning, Pastor Joe, minister at the Word of Life Church in Flowood, Mississippi, the place where Braden’s family worships, texted Richard. He also texted Braden.
Richard thought about Braden breaking his ankle, screaming into his pillow in his hospital room because he refused pain medication. You would think it was a horror movie, Richard said, he was screaming so loudly.
And now, two years to the day, this. “Yeah,’’ Richard said, “that’s God blessing him. Letting him know that what he went through was for strength. Not just to strengthen his ankle and be physically healthy, but be spiritually healthy. He was really put through a test.’’
