Fun fact: White Sox rookie Braden Montgomery's talent was no secret
It is Wednesday afternoon, the day after White Sox rookie Braden Montgomery claimed a piece of baseball history by hitting a walk-off home run in his major-league debut. The home run that his mom, Gretchen, may not have seen, unless she broke tradition and peeked as her oldest son drove a ball over the left-field bullpen, giving the Sox a 6-5, 10-inning win over the Atlanta Braves.
“How about that?’’ exclaimed Hall of Fame broadcaster Bob Costas, imported just for the night to do play-by-play in a throwback telecast with Steve Stone, the team’s regular analyst.
“Talk about drama, talk about theater. And what a major-league debut for Braden Montgomery.’’
BRADEN MONTGOMERY HITS A WALK-OFF HOMER IN HIS MAJOR LEAGUE DEBUT! pic.twitter.com/ifxPs2t57F
— MLB (@MLB) June 10, 2026
Twenty-five years from now, if Braden Montgomery achieves his stated goal of induction into baseball’s Hall of Fame, a million or so Chicagoans will claim to have witnessed Braden becoming just the fifth player in big-league history to hit a walk-off homer in his debut.
“You know, my wife she doesn’t open her eyes, so she doesn’t see it,’’ said Richard Willock, Gretchen’s husband and Braden’s stepdad.
“Me, I’m sitting there,” says Richard, “and I’m going live on Facebook. Just jubilation. Just pure joy. I was just like, smiling, full of joy because I know so many people that love and support Braden were watching, and they get to see and experience it.’’
Richard is out walking Braden’s dogs, keeping an eye on the skies that would soon empty with a fury.
Ollie, the Morkie — a cross between a Maltese and a Yorkshire terrier (Yorkie) — belongs to Braden and his younger sister, Marley. He came along when Braden was a senior at Madison Central High in Madison, a suburb a dozen or so miles north of Jackson, the capital of Mississippi.
Boosie, named after the Baton Rouge rapper who is one of Braden’s favorite artists, is a cockerdoodle, a cross between a cocker spaniel and a poodle. ”He paid a lot more than I would have paid for a dog,’’ Richard says with a laugh. “Brady’s a dog lover. He’s got to love this dog, as much as he paid for him.’’
Chicago streets are not unfamiliar to Richard. He may have just flown up from Jackson a day ago, but he graduated from Leo High School, the private Catholic school on the city’s South Side.
“Here’s a fun fact,” he says.
Richard likes to drop “fun facts” into the conversation.
“Pope Leo, who the school loves and follows and does an amazing job for the world, is a White Sox fan. And now Braden is playing for the White Sox. That’s my fun fact about me going to an all-boys Catholic school.’’
Richard played three sports at Leo — football, basketball and baseball — though he had to give up baseball for 7-on-7 spring drills for football.
He has two favorite memories of his time at Leo. “They’re 1A and 1B,” he said. “The 1A for sure is graduating from high school. Some people might think that’s a given. You know, you should graduate from high school. I don’t take this lightly.
“But for me, I wasn’t always gifted academically. I’m still not. Nothing against Chicago public schools, but I went to Chicago public schools on the South Side. And then I went to an all-boys private Catholic school where my education increased.
“I used to have to take two buses and the L to get to school. I walked from 91st Street, where I lived, to 93rd and Dobson, catch the 93rd Street bus east, get off at the Dan Ryan terminal, take the Dan Ryan from 95th to 79th Street. Get off at 79th, walk upstairs and take the 79th Street bus all the way west to Sangamon. I usually got off at Halsted and walked to Sangamon. That was my route, and I repeated it going home.’’
The 1B?
“It’s only because I was an athlete,’’ he said. “I had a lot of success. The Sun-Times, they did an article on me. I scored five touchdowns in a game at Gately Park Stadium, on 103rd Street.
“That really catapulted me into the recruiting era where, whether it was Bo Schembechler (Michigan) or Hayden Fry (Iowa) or Tom Coughlin at Boston College, they were coming into the South Side of Chicago to see me. Because I scored five touchdowns and put myself on the map.’’
All eyes on him
There were more than 50 family members and friends at the Rate with Richard, a stay-at-home dad, and Gretchen, an emergency room physician at St. Dominic’s Hospital in Jackson, Mississippi.
From College Station, Texas, where Braden was drafted by the Boston Red Sox in the first round out of Texas A&M.
From Iowa, where Gretchen grew up and met Richard at the University of Iowa, where he played football and she launched her career.
Braden’s agents from Roc Nation. His private hitting coach, Jeremy Isenhower. Marcus Montgomery, Braden’s birth father, who also played football at Iowa and lives in Mississippi.
Among those who could not be there but were watching at home was Texas A&M baseball coach Michael Earley, who was the Aggies’ hitting coach when Braden transferred from Stanford.
“I watched it all, man,’’ said Earley, who saw Braden’s first big-league hit, an RBI single in the fourth, before seeing him go deep in the 10th. His thoughts as the ball left the yard?
“I’m gonna tell you what about that kid,’’ Earley said. “That was the most unsurprising thing I’ve ever seen. He’s the most made-for-the-moment player I’ve ever coached.
Exactly two years before Braden Montgomery is making his MLB debut was one of the best college baseball moments
— Jomboy Media (@JomboyMedia) June 9, 2026
He broke his ankle the day before Texas A&M clinched a spot in the World Series. So his teammates helped him join the celebration pic.twitter.com/ec5PH3ooYr https://t.co/YucD42fMCh
“The body, the makeup, the work ethic was off the charts. The skill set was really evident. And just a really cool dude to be around.
Another No. 2?
Fun fact.
“Braden grew up a Derek Jeter fan,’’ Richard says. “The reason why Braden plays baseball now is Derek Jeter. He saw himself in Derek Jeter, being an interracial kid playing a sport that a lot of Black kids aren’t playing. Braden for the longest time wore No. 2.’’
Danny Watkins is the Red Sox scout who tracked Braden when he was in high school. Watkins’ best signing ever was Mookie Betts.
Fun fact. “Mookie and Braden played for the same travel team coach, Tim Dulin,’’ Richard says. “Different times, same coach.’’
Watkins does not hesitate to compare the two.
“Their personalities are very similar, very mature for their age, very aware of their surroundings,’’ he said. “No red flags in terms of makeup or work ethic on either one. And they both showed clear potential.’’
In spring training, Braden said his goal was to make the Hall of Fame.
“He’s being serious,’’ said Devin Pearson, the Nationals’ VP who was Red Sox scouting director when they drafted Braden.
“He wants to be in the Hall of Fame. I think he also wants to be in the Hall of Fame from a business perspective. He’s got business ideas and things that he cares about outside of baseball, too.
“That’s just who he is. He wants to be great.’’
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