From sleeping in a church to the top of the boxing world - with the help of a milk carton

Jessica McCaskill: from homelessness to investment banking, willing a Katie Taylor fight into existence, and becoming a living legend in her own right.

McCaskill Undisputed welterweight champion Jessica McCaskill (L) and her trainer-manager Rick Ramos (R). Source: Ed Mulholland, Matchroom Boxing

ONE DAY LATE last August, Jessica McCaskill received a package in the post. At the time, she was expecting the delivery of four world-title belts, all of which she had won from the previously undefeated Cecilia Braekhus in Tulsa, Oklahoma, a few days beforehand.

McCaskill had denied boxing’s ‘First Lady’ a world record; Braekhus, the female sport’s first ever undisputed champion, had needed just one more win to surpass Joe Louis’ 72-year-old record of 25 straight championship defences in the same weight class but lost for the first time ever in what most considered a stunning upset.

When McCaskill tended to her delivery, she found not a belt but a book: Joe Louis: 50 years an American hero, a 1988 biography co-written by Louis’ son, Joe Louis Barrow, sent to her by the next line of Louis’ kin. Inside, there was a note: “Congratulations on your victory.”

“That helped for it to settle in: what I had actually done in boxing’s history book,” McCaskill says. “Not only was I writing my own way into that story but I also kept another story going.

“I made history and I stopped history at the same time,” she smiles.

“Coach kept telling me to fight for myself, to do it for myself”, McCaskill says of her first fight with the legendary Braekhus, whom she went on to beat even more convincingly in a rematch in March, adding the Ring Magazine belt to complete her set at 147 pounds.

“And for a couple of days beforehand, I was thinking, ‘What does that actually mean, to do it for myself?’

“And it meant acknowledging where I’ve come from — acknowledging my story.

“Becoming undisputed champion was for that weird little girl who never knew what was going to happen the next day, who never knew what life was going to throw at her next. And if I could, I would definitely go back and high five that little girl for being completely random and weird and resilient, because that’s what got me here.”

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boxing-mccaskill-vs-farias Jessica McCaskill. Source: SIPA USA/PA Images


McCaskill grew up in St Louis, Missouri, in America’s Midwest. Born to a very young mother whose own mother was tragically killed in a car accident not long afterwards, she and her brother were raised instead by their great-aunt, Christine.

“My real mother and my real father, they’re kind of distant. I kind of keep tabs on them here and there,” McCaskill explains.

Indeed, she tracked them down over several years but only in adulthood in order to draw a line under the whole thing. So, great-aunt Christine always has been, and always will be, ‘Mom.’

But Mom too fell on tough times. When McCaskill was in the fourth grade, aged nine or 10, Christine went through a divorce which resulted in the family being forced to temporarily relocate to the back of a St Louis church.

“I just remember being there and, you know, that was where we were going to be sleeping,” McCaskill recalls.

Some of the things I remember were, like, if we had cereal in the morning, we’d have evapourated milk — like, out of a can — and we’d mix it with water because we didn’t have a refrigerator. And this was not normal; any other fourth-grader I knew would have been like, ‘Oh my God — what is this?!’

“There were a lot of instances which just make you grow up a lot faster. You have the bare necessities so you cherish them, and your values change. It became a cornerstone for where I was going to grow from; having deeper values and understanding the smaller, simpler things in life, and not being flashy, and not caring what other people say.

“And, in having to grow up so fast, you realise that kids your age are not going to understand that conversation. You have to be an adult and, in any case, you can’t tell people your personal business. That’s kind of the thing that families say, right? ‘Our business is our business and we keep that under this roof.’

It was not the case for me where, ‘a kid is a kid, and a kid won’t know any different’. I knew. It made me hyper-aware of everything: ‘How’s Mom feeling? Is she upset today? [Are we] walking on egg-shells?’ Or, you know, thinking: ‘Don’t use the last of this, don’t use the last of that’. Or convincing yourself: ‘No, I’m not hungry — I’m fine’ because you don’t want to make the problem bigger. All of that made me hyper-aware as a kid, and sensitive to kind of everything.

Thankfully, these days, Mom is doing more than fine. She drives up to Chicago to house-sit and watch the dogs when ‘CasKILLA’ is away for fights, working from home during the week and kitting herself out in Team McCaskill garb come fight night.

Any pre-fight jitters are eased with a prayer as well as the years’ worth of mental preparation that comes with monitoring a “stereoptypical tomboy” daughter who was obsessed with climbing trees and competing with boys at every turn: “who could run the fastest, who could spit the furthest.”

“I think she’s able to relax in her older age and doesn’t have to worry about too much, so that makes me happy!” McCaskill adds.

And to her mind, that contentment for which her mom fought so hard will forever eclipse anything she personally achieves in the boxing ring.

There have been a few times in my life, definite pinnacle moments, that will always override some of those other things. Like the first time we bought a house: we slept on the floor, we didn’t have furniture yet, but we had a house! We were in there, and we all slept together in my mom’s room on the floor. It was amazing.

“Or, I’m a first-generation college graduate, so the day I got my degree in the mail, opening it and seeing it was completely monumental. That was such a major accomplishment in relation to everything else I was going to do with my life. I could say, in that moment, I was a changed person. Whereas becoming a world champion, an undisputed champion — that hasn’t changed me.”

boxing-mccaskill-vs-farias McCaskill lands a right hand on Erica Farias in 2019. Source: SIPA USA/PA Images

McCaskill is a communications graduate. In 2012, she was working at Home Depot’s corporate location in St Louis where she trained customer-service staff.

Home Depot decided to relocate the department, splitting it between Georgia and Utah. McCaskill told her employers that if they gave her a promotion, she’d up sticks and work from one of the two new regions. They instead offered her a lateral career move, so she accepted a severance package.

Before they parted ways, a Home Depot colleague familiar with McCaskill’s work ethic told her he had a sister working in finance in Chicago, about a four-and-a-half hour drive from St Louis. McCaskill was made for finance, he reckoned. He told her to chance her arm. She did.

She fired her CV to an investment bank in the Windy City. She interviewed over the phone. “I can talk my way through any door,” she says. And just like that, she was off.


One of ‘Coach’ Rick Ramos’ core beliefs is that if somebody is truly equipped for his gym, they’ll actually show up and leave all of their external bullshit at the door.

It’s a place of serious work, and he lived in it for three years in order to become the prodigious trainer-manager he is today. Ramos can usually tell after five minutes whether or not someone has the minerals to stay the course in the Body Shot Boxing Club.

So, when he received an email from a novice fighter in September 2013 inquiring about his and his Chicago premises’ availability for training, he responded warmly while remaining sceptical, as always.

McCaskill had been searching for nine months for a boxing base in her new hometown. Having seemingly exhausted her options,
her breakthrough came by way of some social-media fad called ‘Instagram’ in September 2013, when by perusing hashtags she learned that Ramos would staging an all-female amateur card in Chi Town just two months later.

He was the only trainer ever to respond to her queries.

Thankfully, McCaskill didn’t have any bullshit with which she could darken his door. Mind you, she didn’t have much in the shape of equipment either.

“I mean, she came in here, she had like basketball shorts on, loose shirt, I think she was wearing two different-coloured socks, and I’m like, ‘Oh, this girl…’” Ramos winces. “It looked like she had jumped off the bus. And I’m like, ‘Aiite, lemme just…’ — Look, I just want to get the people who don’t want to be here out of the gym. So, I’m like, ‘If this girl is for real, I want to find out and I don’t want to wait.’

So, second day, I tell her, ‘You’re going to spar today, see where you’re at.’ And she just came out of the corner brawlin’. She hit one of the girls from my gym with a body shot and my girl went down. And she was hurt. And I’m just like, ‘Ohhh, man!’ And I was also kind of like, ‘Is this girl Jessica a hothead? Do I have a kind of female Mike Tyson here?’

“And I was just curious as to how good she could be because she was wild — she had a different style to anything that I was used to.

“…And as you can see, I still haven’t been able to get rid of it!” Ramos laughs. “She looks like Katie Taylor in the gym! And then we go out there [into the ring] and she turns into Jessica McCaskill…”

McCaskill chuckles, saying she finds boxing — or at least its premise as the art of hitting and not getting hit — “boring”. She adds: “If I stop to think for too long, then I get hit. I have to be active. I’m an ‘action’ person. I can think while I’m moving, you know?”

And it was all action from the get-go: in her first ever amateur fight, McCaskill headlined Ramos’ all-female show.

As was par for the course for women’s boxing at the time, people who saw the event advertised initially considered it to be some sort of joke. The laughing stopped fairly quickly, though: all 350 tickets were snapped up less than 50 minutes after going on sale.

Ramos recalls:

Jess fought this girl who was just about to turn pro, and Jess gave her — I think — four standing eight-counts; she just beat her up. And the girl never turned pro. She’s actually a friend of ours now. She got married, had kids and she was like, ‘I’m good.’

The brick-fisted McCaskill was subsequently fast-tracked, knocking people out left, right and centre in the Chicago Golden Gloves, winning the competition twice.

After she turned 30 in 2015, she and Ramos made plans for her to turn pro.

Screenshot (12)

“It’s just so ironic,” Ramos recalls. “Like, everything just came together, right? Jess had just turned pro and six rugby players from Ireland had just moved here. They all took my classes and we were cool with them, we would always talk with them. And I used to make fun of them too — one of them used to wear these little shorts, tiny little shorts.”

O’Neill’s shorts?

“Well, I used to always call him Tight Shorts. ‘Take it easy, Tight Shorts!’” Ramos laughs.

“And he would always talk about ‘Katie Taylor, Katie Taylor, Katie Taylor… D’you see Katie Taylor?’”

“– ‘KEE-tee THAY-lur!’” interjects McCaskill, in stitches, with what can be described only as an excellent impression of a Scottish person.

“The Irish guys would always talk about Katie,” Ramos continues. “And one day I’m like, ‘Let me look her up.’

“But after the [2012] Olympics, she was kind of quiet for a bit, and then in the UFC, Ronda Rousey just took off.

“And I honestly started to gun right after Ronda Rousey because she was supposedly about to make a crossover into boxing; she was on the cover of Ring Magazine wearing an MMA glove on one hand and a boxing glove on the other. And I’m good friends with Oscar De La Hoya’s brother, Joel, as well as a couple of guys who work for Golden Boy (Oscar De La Hoya’s promotional company). So, I really was pretty confident that I could make that fight because Jess was like 2-1 or 3-1 as a pro at the time — she was the perfect opponent.

“I kept telling people, ‘Ronda Rousey does not have a chin and she cannot fight. Put one on her chin and its over.’ And people were like, ‘Wooahh‘, you know, because at the time, Ronda was a megastar. It felt like the fight was becoming doable.


Ramos, however, was right. Too right. Rousey got sparked in the Octagon by former boxing world champion Holly Holm. Her aura of invincibility dissipated and so too did any shred of credibility to a Rousey-boxing crossover.

“Then Katie turned pro,” he recalls. “‘This Katie Taylor girl is still around?’

“So, then I’m like, ‘How do I get into this thing? How do I make this happen?’”

That’s where Ramos’ and McCaskill’s self-promotional genius properly kicked into gear. Likely before Taylor had even heard of McCaskill as a potential opponent, they created a missing-persons notice for her on a milk carton, cheekily suggesting that the WBA lightweight world champion had gone into hiding to avoid the less experienced American.

Beneath the word ‘MISSING’ and a picture of Taylor, they listed her physical traits: Eyes: Brown. Hair: Brown. Height: 5-5. Weight: 135 [lbs].

“If you can identify this woman,’’ the next sentence read, “please report any information you may have to Body Shot Boxing Club, Team McCaskill.”

They plastered it all over social media, with McCaskill providing accompanying goading in video form. (In her film, Katie, we see Taylor being shown one of the videos at the time by her manager, Brian Peters. “Who does she think she is?” Taylor responds, brow furrowed, genuinely annoyed).

Then, in July of 2017, Ramos caught wind of Taylor and her team claiming they had approached 20 prospective opponents only to have each of them turn down a fight with the Irish icon before another unheralded American, Jasmine Clarkson, stepped in for a payday and a pummeling.

“That’s my in!” Ramos recalls, beaming. “That’s my in!”

He posted his phone number on Facebook, inviting either Taylor’s manager Brian Peters or promoter Eddie Hearn to give him a shout about a fight with McCaskill.

He first answered the phone to an opportunistic writer from The42, however, and he stirred the pot further in an impromptu interview. Ramos accused Taylor of ‘disrespecting women’s boxing’ when she demanded that fighters in her division “step up”, explaining that McCaskill would have jumped at the opportunity had she been one of the 20 women supposedly approached prior to Taylor’s last fight. “Nobody called us.”

Within weeks, and truly from nothing, Ramos and McCaskill had willed it into existence through brazen arse-chancery: a 135-pound world-championship shot against Taylor in London in December 2017; a Wednesday-night headline event on Sky Sports.

And even in gallant defeat on the night as it transpired, it was a fight which propelled McCaskill into the mainstream boxing consciousness as well as Eddie Hearn’s good books, and onto a legendary run of fights in which she has become a two-weight world champion and undisputed 147-pound queen.

jessica-mccaskill-in-action-against-katie-taylor McCaskill and Taylor trade at London's York Hall. Source: James Crombie/INPHO


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It’s no exaggeration to suggest that in the three and a half years since she lost a decision to Taylor, McCaskill has pieced together a Hall-of-Fame-worthy professional boxing career. She is a living legend of the women’s game, as she continues to discover.

“You know, we just came back from Atlanta and I got to speak to a lot of female fighters at a boxing event there. They were pretty excited to see me so that’s still kind of weird, I guess,” she smiles.

“They kind of fumble and stutter and get really excited. They’re just happy to get a little bit of motivation or advice — whether they won or they lost. It’s really cool.”

All the while, she continues to work her day job at an investment bank in Chicago, dealing with its Asian clients from 6am to 3pm which frees her afternoons for training.

McCaskill has never needed to box for money. But at 36, looking around from the mountain top, does she still need to box at all?

The thing is there are always other mountains, and there remains one that CasKILLA and her trainer-manager remain hellbent on conquering should the conditions allow it.

“I definitely think we deserve the Katie Taylor rematch,” Ramos says. “I don’t think there’s a bigger name out there for Katie. Obviously, they have a history, they’re both undisputed, Jessica’s career has skyrocketed ever since the first fight…”

So, why hasn’t a Taylor-McCaskill sequel happened so far?

“Because they know she’ll get beat,” Ramos says abruptly. “She’ll get beat. Honestly. And I feel like every time Eddie or the boxing public mention a fight between Jess and Katie, they (Taylor’s team) extend the finish line by 10 feet. Brian Peters told us to keep winning and we’ve done that. We’ve done everything he and Eddie told us to do and we’ve done everything we said we were going to do, but still no fight.

“A lot of people give Jess credit for the fact that her last six fights were all for world titles. That’s because they keep trying to get us beat! It just hasn’t worked yet.

“They know Katie’s getting older, she’s not getting better — I mean, Jess has improved drastically as she has progressed while Katie is still doing the same old Katie stuff. And I want Jess to be the first person to beat her because if Katie loses before that, I don’t really have any interest in her. We want to beat her now.

“Eddie said around the last fight (Braekhus rematch), ‘Oh, Jess and Rick don’t get the credit they deserve.’ Well, give us the credit, then. He’s in control, right?

“And you know what? Jess was the first one to step up when Eddie and Katie said they called 20 girls and nobody would fight her. So, now that we’re undisputed, Katie should step up.”

In Taylor’s defence, her own CV scarcely reeks of ducking worthy adversaries: her own last six fights rival McCaskill’s incredible run and, in reality, any recent sequence of fights in all of boxing, female or male.

For the entirety of her own professional career, the 2012 Olympic champion has laid plain that she’s open to fighting anyone and everyone but that equally, she’ll generally fight whoever is proposed to her as an opponent by her team.

“She doesn’t deserve credit for saying that she’ll fight whoever”, McCaskill says firmly, “because Katie has the power to say, ‘I want to fight this person — make it happen’, and she doesn’t. So no, she doesn’t deserve credit for that at all.

“I’m hot right now — I’m at a very obvious peak in my career and you don’t necessarily go after something like that unless you’re ready. And by them dodging it, it just solidifies the fact that they’re not ready. They may be trying to wait me out, wait until I’m a little older… It looks like a plan to dodge me, basically.

She’s had a lot of amateur fights: she started early and maybe she peaked early, and now she’s on a downward trend. I see some of the same vulnerabilities in her now that I saw in 2017 — I’ll tell you that. She still has some of the same old issues that she had before. What’s different is that I was very green back then, but this time I believe I would be equipped to capitalise on those vulnerabilities. And I think she and her team know that, too.

“She has no defence!”, Ramos adds. “Her defence is offence. If you throw at Katie, she tries to throw with you and finish last — so she kind of steals exchanges and steals rounds. It’s very amateur-ish — but elite-level amateur. It’s smart.

” But everyone touches her. I feel like she’s easy to draw in. She even says that herself. I feel like she’s been in way too many wars.”

“Too many,” agrees McCaskill. “Her body has been through way too many fights. In boxing terms, her body is just old. Whereas I’ve had, I think, 37 fights altogether, amateur and pro combined. My ring IQ, my angles, my ability to apply pressure and control the fight — I’m just getting better.”

“And I give it to Katie,” says Ramos.

She’s tough as balls. But the hourglass has almost reached its end. I think at 144, 145 [lbs], if Jess touches her with a big right hand or a left hook, I think she could stop her. I don’t think Katie is foolish enough to get caught clean and knocked out by one punch, but I think we could stop her — too much strength, too much power, too much pressure.

Hitting the brakes a little bit, both McCaskill and Ramos stress that they have nothing against Taylor personally, and that this line of attack is purely about not getting a fight they believe themselves to be ostensibly owed.

“We were in New York when she fought [Delfine] Persoon the first time and we saw her at breakfast and wished her well for the fight,” McCaskill recalls. “There’s no animosity there on my part…

“…Although I did make a Katie Taylor pinata”, she laughs. “It was for Cinco de Mayo — I had a meet-and-greet on the day of her fight (v Jonas) so we did a video and wished her luck, but we also had a Katie Taylor pinata for all the kids who came to the meet and greet. It’s just light-hearted — nothing personal.”

Image from iOS

Image from iOS (1) McCaskill's Taylor pinata.

McCaskill still has the milk carton too, but she hopes she can leave it in the fridge this time around and create the fight through more conventional communication.

“If we beat Katie, we’ll bounce,” Ramos smiles. “I’ll say to the DAZN cameras, ‘I fuckin’ told you,’ and just leave; I’ll go grab a cheeseburger with Jess and talk about the night. I think that’d be it. She could join me training, managing fighters — I could use the help!”

“It would probably take some convincing to find somebody for me to fight after that,” McCaskill agrees. “That’s all I really want. You get one belt, you get all the belts, you beat undefeated people; and if Katie’s still undefeated and I beat her, I’ll have taken two zeroes from the records of two legends.

“That’s the legacy I’m trying to build and I wouldn’t want to jeopardise that legacy by unnecessarily prolonging my career when I could be helping other fighters instead, using my career to build new careers…

“To make new stories.”

– First published 23.55, 30 June

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