The conqueror of Cecilia Braekhus was homeless as a child but now balances a job as an investment banker with her in-ring life, where she is set to defend the undisputed welterweight championship that she won last year in a stunning underdog story; could McCaskill fight Katie Taylor again?
Wednesday 27 January 2021 20:01, UK
Colleagues in the office understand that Jessica McCaskill is just as fierce during her day job as she is inside the ring.
McCaskill is one of the great boxing success stories but there is much more to her than just being the undisputed welterweight champion.
She was homeless as a child in Chicago during the 1980s, a period when the city struggled and people were forced onto the streets in increasing numbers, but has incredibly forged simultaneous successful careers as a boxer and an investment banker.
"I don't have to struggle with the mental elements that come with being in a combat sport."
"Those two worlds intermingle more than people might think," McCaskill told Sky Sports.
"They are both very male-dominated where the female has to outshine them, take control, do her thing.
"I do what I do and people fall in line.
"I am aggressive with both; I take the initiative to do extra work-outs and to take on more work.
"I am fearless to try new things, to jump in, to lead the pack."
Her difficult start to life is now a strength inside the ring, she believes.
"It took away some of the mental struggles that people have in this sport," McCaskill says.
"I didn't worry about anything."
She shrugs: "I became fearless. Why should I be afraid of anything?
"I don't have to struggle with the mental elements that come with being in a combat sport."
McCaskill reacted to last year's shocking upset of Cecilia Braekhus, her peak moment in her boxing career, by dedicating it to "fourth-grade Jessica" - the young version of herself who never gave up.
"I've had a lot of different points in my life where I was up and down, in and out," she remembers.
"I had very humble beginnings. We were homeless, we had struggles.
"It made me grow up very fast as a kid to work through these things.
"There were a lot of times when we went without. I've had Christmases where I didn't get any presents and I just had to keep my chin up. I had to grow up.
"So [beating Braekhus] was for the person who had to sacrifice. I gave myself a present."
McCaskill's upset of Braekhus, who was undefeated in 36 fights and considered one of the pound-for-pound best in women's boxing, means she must be held in similar esteem to the likes of her former opponent Katie Taylor and Claressa Shields.
Unlike Olympic gold medallists Taylor and Shields, McCaskill did not benefit from a lengthy and decorated amateur career. She found boxing just by chance.
"That person that I started out being was always competitive and into sports. It was my outlet," she said.
"But I was never in an individual sport, I always did cheerleading, basketball, flag football.
"One day I walked into a gym and did a kickboxing class, and loved it.
"In the same gym, there was a boxing coach. After my trial period with the kickboxing, I went over to the boxing.
"The first time I got punched in the face I thought: 'That wasn't so bad! Now it's my turn…'
"It's all fun and games until you get punched in the face. Then it gets real - what do you want to do?
"I didn't have a problem with it at all.
"I felt like I was dominating, especially the other females.
"I had a lot more power than anyone that I was sparring with.
"There weren't a lot of other females to begin with so, from an early part of my career, I sparred with men and older teenagers - people who were faster and stronger than me. That helped me."
McCaskill agrees that women's boxing is an altogether different entity to what she discovered a generation ago.
"Definitely," she said. "Now I'm a person that other fighters look up to - men and women. I'm at the top giving what I wish that I had, back in the day.
"When I first started I didn't have any female fighters to follow or look up to.
"I went from what I found in my own gym which was only male fighters. There has always been a higher ratio of males to females but now? I wouldn't say it is catching up but there is a stronger presence of female fighters.
"You see big knockouts, undisputed champions, unified champions, great headliners - the quality of women's boxing is rising as well as the numbers.
"Female fighters are always good to watch, always intriguing. Maybe that's because of the two minutes [rounds, as opposed to three minutes in men's boxing]."
These days McCaskill's days are long and structured - how she likes it, to stop the mind from wandering back to memories of her old life.
On the day she spoke to Sky Sports, her first work-out was a run at 4:45am before she logged onto her laptop to do her banking job. Two more work-out sessions were planned for the afternoon and then, in the evenings, McCaskill teaches a boxing class for non-professionals.
Her role at an investment banking firm, which she still commits full-time hours to, is a success in itself. Co-workers know not to mess with her.
"I bring in my belts for everyone to see because I'm a big community person," she smiles. "They buy the newspapers, they love the stories, I sign things for them.
"I make sure everyone in the office has a t-shirt so they all represent. They are a part of this experience as well.
"Even my co-workers in London and Dubai know, they will ask me questions about things."
When McCaskill lost to Taylor in London in 2017, much of the crowd was actually backing the American.
"People from my current bank and a previous bank that I'd worked at bought tickets. I had support in the flesh which was amazing."
As success inside the ring escalates, the finance world may lose a champion.
"There may be a time when that changes," she says of her day job.
"I don't mind doing both, it helps me to keep a strict schedule. I just move from one thing to the next.
"Over time it will come into play - is it time to give up the finance world? I am very dedicated to boxing so need to make sure I put myself in the best position, mentally and physically."
McCaskill is a contender to rematch Taylor in the future in what would be a battle between undisputed champions of different weight divisions.
But first, she will defend her belts in a second fight with Braekhus on March 13 in Texas.
"I don't know what more Cecilia can bring that would be outside of the box," McCaskill insists.
"The first time we prepared for two types of fights. She brought the aggressive, big puncher type of fight. So we've seen that and we've seen the other type of fight that she brings.
"It doesn't seem like there will be any shocking elements.
"I just kept going. I'm a pressure fighter. It's hard to make me stop or slow me down. It's 20 minutes of fighting and my training is impeccable."
The first fight produced a historic result, McCaskill is reminded.
"I always wanted to impress this element onto female boxing - making history, being the first to do things."
Her unorthodox route is as pioneering as it is inspiring.
