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From homelessness to undisputed world champion, Jessica McCaskill’s tenacity has driven her forward

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Jessica McCaskill pulled the upset last week, but she wasn’t surprised at all.

Ed Mulholland/Matchroom

Last weekend, boxing reminded you how good it can be, why it still matters, and introduced you to Jessica McCaskill, if you hadn’t already acquainted with the 35-year-old Fighter — yep, deliberately used that capital “F” — who upset Cecilia Braekhus in Oklahoma, and on DAZN.

The Chicago resident McCaskill entered the ring in downtown Tulsa the underdog, with the undefeated Braekhus getting a lion’s share of love by the hypers who were hoping under their breath that she’d win, setting up a higher-profile scrap with the winner of the next weekend’s Katie Taylor-Delfine Persoon rematch.

I was curious, what was McCaskill’s level of confidence that she would be messing up some best laid plans? Did McCaskill know she’d beat Braekhus?

“Going in, I was very confident, when I added up everything coming together, I thought it would work in my favor,” McCaskill said, on an audio call. “Yeah, I felt it would happen the entire time.”

Coach/manager Rick Ramos owns a gym (Body Shot Boxing Club in Chicago), so she was able to train in a controlled environment, and got solid sparring work. Hearing media or fans talk like it was a given that Braekhus would leave Tulsa 37-0 didn’t get under her skin.

“We’ve always been the underdog,” she said. “That didn’t take me by surprise.”


A few days after the victory, I checked in with the now 9-2 titlist. I wanted to get a bit deeper into that portion of her history which so moved me, her days dealing with being in fourth grade, and being homeless.

Jessica and her two older brothers lived in Belleville, Illinois, in the southern part of the state — it’s 16 miles from St. Louis — with her great aunt Christine, whom she thinks of as her “mom.” Christine dealt with a divorce, and the whole gang sort of fell through the cracks. Adrift and unable to pay rent, a church took them in.

“In the middle of fourth grade,” the boxer told me, “I was kicked out of my grade school. They found out I moved past (the line which allowed students to attend that facility). They packed up my desk.”

McCaskill paused. She was back in that moment. I felt a bit bad, she’d just finished telling me that she was still knee deep in euphoria.

Ed Mulholland/Matchroom

“I changed schools, and we lived in the church for a handful of months. There was no refrigerator. Maybe there was a microwave, or maybe it was a toaster. But I looked to mom, and I saw her strength. Did I feel different from the other kids? It’s one of those those things, it makes you grow up real fast. You can’t compare yourself to other kids, you can’t really talk about your life, people won’t understand. Me talking about how I was kicked out of another school? Yeah, I was not gonna be having that conversation.”

And so a nine-year-old has to sit with complex feelings, maybe a combo of anger, shame, and fear. The other kids are talking video games, shows they like to watch, what was said in history class. McCaskill’s story got me thinking about living in New York, the stories I’m hearing about people out of work who are four months behind on rent, and worried that tolerance will cease, and a tidal wave of evictions will soon be put in motion.

McCaskill is a special sort, in the top 1% or so on the combined mental/physical toughness scale. She has been able to use the experience as fuel, but what about those not able to rebound with the same tenacity? Maybe a few can boost their own spirits and energy when dealing with looming homelessness by harnessing some McCaskill spirit?

While the uncertainty from COVID has inserted itself into many peoples’ minds, de-stabilized them, not so with McCaskill.

“I could have very well kept that homeless mindset, but instead my mindset was and is, ‘I’m unable to be crushed. I can get through anything.’’’

The grit and willpower were in evidence in that main event on the Matchroom card. McCaskill last Saturday threw more (499 to 269, according to CompuBox) than Braekhus, but this must be pointed out, again, credit should be given to judges Gerald Ritter (97-94) and David Sutherland (97-93) for scoring it how they saw it, for the underdog, instead of the more heralded athlete.

McCaskill waited for the ring announcer to end the dramatic pause in Oklahoma, and when he said “new,” she was now the undisputed welterweight champ, emotion flooded her system.

She held it together quite well in the minutes directly after he life changed so considerably, cracking wise to Todd Grisham and Sergio Mora about streaking. Then it dawned on her, how far she’d traveled. Her coach Rick Ramos had told her she could win, and reminded her that if there was a point when she doubted herself, she should remember the strength of will she summoned in fourth grade.

During the 10 rounds, McCaskill stayed focused and didn’t fast forward or start thinking about something that would be out of her control, that being how the judges might be scoring the action. Instead, she looked at the Norwegian vet and dissected what was in front of her, and how she could best use her skill set to maximal effect.

“In the first minute of the fight, I wanted to see what she was going to do, would she jab and move, or come forward,” McCaskill said. “Cecilia was presenting herself to me, all the way through, so I just pushed the pace.”

As I watched, it did surprise me when I saw Braekhus so squared up at times, I shared. “I expected more jabs, her to be on her bike,” McCaskill answered.

Hey, that made for a better fight, and it’s always so easy to from the sidelines weigh in and offer a theory why someone in the arena “failed” and try to sound smart by announcing the strategy that should have been employed.

“I wanted to see, what can I get off, would she bite off my flinches.”

I admitted, if I was someone who didn’t come to the fight having done some homework, I would not have known that McCaskill isn’t some young gun who used a better stamina reservoir stemming from an “age edge.” The Illinois fighter turns 36 on Sept. 8, in fact. Braekhus, a welterweight titlist since 2009, turns 39 on September 28. McCaskill laughed when we spoke about how a youthful visage can result in assumptions.

“I guess it’s good genetics, and good defense!”


It’s human nature, we find someone like McCaskill, so easy to root for and we come to hope that she gets more make-up calls in life, that outside the ring things fall into place and she achieves serenity and closure in her personal life. McCaskill said that she has met her birth mother, she went to find her in Illinois.

“I met my blood brother and sister, my dad I haven’t met in person, we’ve done text messaging,” she said. “We’re still pretty distant. Hey, Christine is what I have and need and love.” Yes, she says, it’s correct to say she was “adopted” by Christine.

Coincidentally, or not coincidentally, probably, Braekhus was also adopted from Colombia when she was two years old. She never knew her birth parents or why she was given up.

Christine, by the way, didn’t come to Tulsa to watch the fight with Braekhus, but made herself massively useful regardless.

“She came to Chicago to house sit for me, with my two pitbull rescues,” McCaskill said, laughing. “I made sure she knew how to get DAZN on the TV!”

In the days after she had her hand raised, McCaskill said how she felt about the win changed up some. People saw her near tears when talking to Grisham and Mora.

“Am I still at the same level of high? There’s no comparing to the high on fight night, the actual night of. There’s the hustle and bustle, you’ve been there for a week. But then I packed up, I was trying to fit all my stuff into a duffel bag, and I went home and crashed.

“It’s still an amazing feeling, people are still contacting me, calling me, my phone was going insane, people were contacting me on social media. There’s a lot of love. It’s a different kind of high. I told someone the night of, I felt unbalanced. I’d look up, I’d be on my phone, it was 3 am, time was escaping me. But I’ve been enjoying the moment. Now I’m trying to get back to normal.”

Starting Monday, probably, she will go back to the “regular” grind. That means getting up at 3:30 am to do a workout. This past week, she was back to her day job, so she’d get up at 4:45 am, to be in for 6 am.

She’s been at the Chicago futures brokerage R.J. O’Brien for about four years, and does her thing in the regulatory reporting department. Basically, she helps make sure that all the figures match up, make sense, and are filed and processed and declared in a manner that follows industry regulations to a T. One could excuse her, if, at her desk, she gets a faraway look in her eyes. She planned to watch Taylor-Persoon 2 and she’ll tell you that she’d like the Irish star to win. She has seen Taylor up close over 10 rounds in 2017, where Katie snagged a decision victory.

“I want Katie to win,” said McCaskill. “Katie is one of the biggest fights for me outside of a Cecilia rematch. We just have to go to the drawing board and figure it out. I hope to fight before the end of the year, but we have to see how Katie gets out of this fight. If she’s cut or anything like that it will take longer with suspensions but I’d love to fight before the end of the year. I am already back in the gym so I am staying ready.”

You don’t dare interject with anything resembling a hint of dubiousness when she articulates her desired scenario of how a Taylor vs McCaskill rematch would look.

“Something like Wembley Stadium where there are 100,000 fans, if that’s even possible in the times that we are in right now, then of course that is something we wouldn’t pass up. Our preference is to have the fight in the States since the first fight was in the U.K. This one should probably be in the U.S. If it was in Chicago, it would be insanity. It would be massive.”