By Jana Allen
It was April 22, 2010, when Kelli Masters made history without even realizing it.
That was the night of the NFL Draft and Masters, who had been an NFL agent for just four years, was representing Gerald McCoy. It came time for the third overall pick, and McCoy’s name was called, drafted by the Tampa Bay Buccaneers.
During the hustle and bustle of the event, taking care of McCoy’s family, making sure they got on stage for the pictures and simply doing her job, Masters didn’t once think about this being ‘her moment.’ However, she had just made history as the first woman to represent a top-five, first-round draft pick and only the second woman to represent a first-round draft pick at all.
“I had the satisfaction of, ‘Okay, this was a goal and I’ve reached (it),’” Masters said. “But it wasn’t something that was about me.”
In a male-dominated industry, Masters has been making waves for over two decades now. She owns her own Oklahoma City-based agency and has a clientele of about 30 athletes, 8 of those being NFL players.
This wasn’t always her dream, but she knows she has found her calling.
‘If you’d been an agent, we would have signed with you’
Before Masters career as an NFL agent, she was working for Fellers Snider law firm doing litigation and nonprofit law. She began doing legal work for former NFL players, helping them out in the creation of foundations.
She hadn’t worked in the sports legal world before, but one former player’s mother said something that caught Masters off guard.
“(She said,) ‘Where were you at the beginning? If you’d been an agent, we would have signed with you,’” Masters said.
This was something that had never crossed Masters mind as something she wanted or was supposed to do, but after that she couldn’t get the idea out of her head.
So, like any good lawyer, Masters began doing as much research as she could. For months, she talked to anyone and everyone she could get ahold of and gathered all the information she would need about the world of being an NFL agent.
“After about a year, I realized it was probably the most insane career move I could make,” Masters said. “It made no sense. But at the same time, I also knew I had found my calling.”
So, she took a leap of faith and founded KMM Sports.
And Masters was no stranger to career changes. She received her Bachelor’s degree from the University of Oklahoma in Journalism, with the plan to become a broadcast journalist.
Before she could fully launch into her career in TV news, Masters decided that she would go to law school to become a better journalist. She felt that it would give her an extra skill set and help her better understand a lot of the things she was covering.
In the middle of law school, she decided she would practice law instead of returning to the studio. And then, just a few years later she again made a new career decision: starting her own sports agency.
‘I didn’t plan on being the first anything, I didn’t plan on being a pioneer’
At Masters’ first NFL Combine as an agent, she was approached by one of the more successful agents for some unsolicited advice.
“(He) point-blank told me I didn’t belong there,” Masters said. “That women never make it as agents… And I said, ‘You don’t know me, you don’t know I am here. I’m going to prove you wrong.’ And I have.”
At the time, Masters said there were about a dozen women who were agents, and only two or three who actually had clients on NFL rosters.
Just being a certified agent doesn’t guarantee you clients, and it especially doesn’t guarantee you will have clients that actually get signed by teams, Masters said.
Today, out of 795 total NFL agents, 41 of them are women; of those, only 21 have a client on a current NFL roster, Yahoo Sports reported in May, attributed to the National Football League Players Association.
It’s also extremely rare for an agent, man or woman, to go out on their own and start their own agencies, Masters said.
“Not only is the agent business brutal, and highly, highly competitive, it’s also virtually impossible to start an agency and compete against the established companies,” Masters said.
But she did exactly that because she said she knew she wanted to approach representing athletes different than most agents did.
As a lawyer, Masters said she was in a “protection and advocacy” mindset.
“As opposed to just negotiating the biggest deal, I look at every situation very comprehensively, almost like a general counsel of a company,” Masters said. “On the personal side, I genuinely care about the person that I’m representing, not just his athletic ability.”
Dale Reneau III, director of Operations for KMM and lifelong friend of Masters, said Masters’ agency has an extremely high retention rate compared to most others.
Reneau III said he believes the reason Masters has found so much success is the way she treats her clients.
“Every decision she makes, even from the beginning of the recruiting is what’s best for the player,” Reneau III said.
‘With Kelli, you feel like you are ‘The Guy’’
Tress Way, punter for the Washington Redskins, has been Masters’ client for over six years, signing with her when it was time for him to enter the 2013 NFL Draft.
Way said Masters is a rare kind of agent. She consistently checks in on his overall well-being, along with sending an encouraging message or prayer before every game.
“I say this pretty proudly, just to kind of really boost up what Kelli does: I can confidently tell you that I don’t know of anybody in my locker room that has that kind of relationship with their agents,” Way said.
Masters doesn’t make you feel like just another one of the players she represents.
“With Kelli, she makes you feel like you are ‘The Guy’” Way said.
Way said there was a time when he was considering no longer playing in the NFL. It was 2013, and he had just been dropped by the Chicago Bears who had signed him as an undrafted free agent just months earlier.
A job offer had come up in Oklahoma City, and Way and his now-wife were weighing the options of him moving back to Oklahoma versus continuing his career in the NFL. Way reached out to Masters for advice, and after hearing him out she told him she still believed he could make it.
“She just said, ‘Hey, Tress, this is how it goes with kickers and punters, you have the hardest time actually cracking the surface and getting in. (But) once you get in, and you prove to everybody what I know you can do, you set yourself up for a great long career. But you’ve got to withstand the battles and the adversity right now,’” Way said.
So, after talking it over with his girlfriend and family, he decided to give it another try. The Bears signed him in 2014 but waived him again before the season started. However, just two days later he was claimed by the Redskins and is still with them today.
In his rookie season, Way led the league in gross punting average with 47.5 yards per punt. But he may never have gone on to the Redskins had he not had an agent like Masters who believed in him more than he believed in himself.
‘If I don’t get this, it’s going to change the way the rest of my life works’
Masters said she feels like another thing that helps her stand out from other agents is that, as a former athlete herself, she can relate to those she’s representing.
“I understand the sacrifice on a daily basis to be better,” Masters said. “Doing the things that nobody sees, so that when you do step onto the field, you’re prepared to be at your best.”
From a young age, Masters and her twin sister began to dream of becoming the baton twirler for OU.
“The twirler at half-time just captivated me,” Masters said. “She’s out here in a funny costume and she’s throwing her batons in the sky and everyone’s cheering. I just thought, that’s what I want to be, I want to do that.”
One had to have national recognition to be considered for the OU twirler spot, so the competition was on, so to speak. Masters mother became their daily twirling coach, practicing 4-6 hours a day.
The twins attended a Tahlequah twirling camp a few summers in a row, where they got connected with the OU twirler at the time and ended up driving to Norman to take lessons from her.
When Masters was 14 she won her first national title and later became a world champion in baton twirling, all to become the twirler at OU.
When it was time to audition, the Masters twins tried out against each other, knowing either one or neither of them would get it.
“And I remember that day thinking, how I do today is going to determine what my life looks like because I’ll either be twirling for Oklahoma, fulfilling my dream, or I’ll be moving to a different state,” Masters said. “I just realized the gravity of the situation, that this is my entire life goal… And if I don’t get this, it’s going to change the way the rest of my life works.”
A few weeks later, the twins were called to the principal’s office of their high school in Midwest City. They were told OU’s band director had called and wanted them to come to Norman to talk to him.
Masters recalls the heavy silence between her twin and herself on the half-an-hour car ride as the two had no idea what news they were soon going to hear.
Thankfully, it was better than they had ever hoped for. They were both OU’s future twirlers.
“The ultimate goal was being a twirler for OU and my sister and I achieved that,” Masters said. “It was the experience of a lifetime.”
Masters was right about the decision OU would make deciding what the rest of her life would look like. If she hadn’t gone to OU, she may never have gone to law school, become a lawyer, or ever be approached by former football players because of her connection to OU.
After the 2010 NFL Draft ended, Masters said there were dozens of messages from colleagues and friends congratulating her, but it didn’t make the news and wasn’t something she was widely recognized for immediately after. A few years later, Masters was contacted by a member of the media to talk about that night, about being “the first.”
Originally declining, Masters decided to go ahead with the interview in an attempt to inspire others.
“I thought, there are maybe young women out there, people out there, that are holding back on pursuing things that they want to because they don’t see anyone else like them doing it,” Masters said.
Masters said she started receiving messages from women all over thanking her for sharing her story, and she’s thankful she can be a point of inspiration for anyone who is facing an uphill battle, just like she did when she walked into that room full of other agents for the first time.