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Lamonte Winston:
The Player Development Guru
By: Julie Nelson


“Trust starts with truth and ends with truth.” – Santosh Kalwar

In the game of football and life, Lamonte Winston knows the importance of building relationships and ultimately, trust with players.

Winston, who is entering his 28th year in the industry, has over 25 years of experience advising and consulting professional athletes in both life skills development and post-NFL career development.

Today, you will find him sharing his experiences and talents at his business, The Winston Group (TWG), where he consults with high school and collegiate athletic departments and player development professionals about building world class programs for athletes.

“TWG helps leaders navigate and adjust to the increasing opportunities for athletes whether it’s personal branding opportunities or the next thing on the horizon,” said Winston. “I have enough subject-matter expert connections that if a person has a need or special circumstance, I have the contacts and way to connect them.

What I really love is working with people, not just athletes, when things aren’t going well. That’s when I’m at my best. You can say it, but when you’re working with people from the inside out, that’s what you’re dealing with.”

The San Francisco State University graduate and former wide receiver started his career as an assistant football coach in the collegiate ranks for years before transitioning into the National Football League with the Kansas City Chiefs as an administrative personnel assistant in 1993.

“Coaching was part of my steppingstone, but I didn’t want to be a coach forever,” said Winston. “I really wanted to be in personnel. I love evaluating talent. I wanted to be a general manager, but God had other plans for me. I did not know that I would have a 24-year career in pro football through something that wasn’t even on my radar. That was my start in it.”

Two years into his stint, he was approached by then Vice President Tim Connolly about watching a video on player programming. He was told, “If this takes up more than 12% of your time, it’s not worth doing.”

However, Winston found the film and information to be very beneficial for the team. The NFL produced a 12-minute segment on player programs which talked about internship opportunities and family assistance. It was an eye opener for Winston about what available resources were out there for players and their families and was encouraged to attend the NFL Business Symposium to learn more.

At the time, the Chiefs did not have anyone in the ‘player space’ that was working directly with players in the engagement capacity. Then Vice President of Player Personnel Lynn Stiles informed Winston that they might not have a full understanding of the responsibilities but with support from then General Manager Carl Peterson and Head Coach Marty Schottenheimer, Winston was tasked with building programs that would help players excel in other phases of life.

He spent 17 years with the Kansas City Chiefs, including 14 as Executive Director of Player Development, and is a founding member of the NFL Player Development Steering Committee. While in Kansas City, Winston established the Chiefs Player Development Program and the NFL/ NCAA Champs Life Skills Program to educate athletes on the business of the NFL and their preparation for life after football.

“My engagement with the athletes was really about developing relationships and their awareness of where they are, their circumstances, and learning how to strategically, safely confront things in their lives instead of hiding it before it becomes a problem.”

Life doesn’t discriminate or protect you because you are in the NFL. When it comes to the success and support of players, heads of player engagement (HPEs) are responsible for “everything outside the stripes” and play an integral part in building a stable locker room. They help players manage everything from mental to financial health and will guide those navigating major life changes, like a divorce, loss, or the birth of a child. They game-plan in a different way by devising strategies for building a support system around each individual on the roster and practice squad.

This role allows players to learn how to get pertinent information that will allow them to make alterations in what they do and how they do it without changing who they are.

“I’ve often said the players are employees, too,” said Winston. “They deserve to have HR. They deserve to know what’s going on. They deserve to know a lot of things. They need to understand what the business side of this looks like and therefore, how that impacts their whole ecosystem. Not only for the players, but it’s really helping them learn how to educate their families, their friends, and their relationships about what they all are in for."

For the Oakland, California native the value of this position helps players understand how to effectively communicate. It helps them understand how to build trust when they don’t come from areas of trust, especially with men other than with football coaches. It teaches them about accountability to an organization that’s going to help you when this game leaves you because it’s going to leave you. The role of the person in this position is vital because they help players clear out and see those blind spots. It’s important that the good HPEs go further than the players and they get to the families and help them understand this is different than college football.

A well-respected leader and mentor, Winston relates to players on another level and provides real life examples of things he himself has experienced.

“Everyone feels that their son or boyfriend or husband is going to get taken away from them,” said Winston. “The answer is, ‘yes.’ Who’s going to take them away? Pro football. Football is the only relationship that they are going to enter in to and fall in love with that’s going to tell them, 'you know I’m going to leave you, right? for someone better.' I’m not going to tell you when, but I am going to leave you. And you know what they do? They just fall in love and then get mad at her when she leaves. Well, she said she was going to do it. You have to take care of her while you can.”


When the Chiefs ‘divorced’ him in 2010, he found himself in a similar position of ‘what now?’ He just knew he needed to regroup and use all the tools and resources he had been given to apply to his next venture.

Thus, The Winston Group was established.

“I wanted to create The Winston Group because I felt my name and experience at least gave me some credibility,” said Winston. “We do programming and consulting whether it’s working with athletes in challenging circumstances or draft eligible juniors and seniors preparing for the draft or providing resources for personal and professional development.”

Knowing this is where he was called to be and wanting to stay in the ‘player space,’ Winston confirmed what he truly believed his purpose was with ‘Pushing Excellence.’

“That became my tagline,” said Winston. “I started in Kansas City reaching out to high schools. The model was to train former athletes and put them back in the schools and in front of students. We would give them a level of education that’s relatable to the students and for those athletes that are participating, we would train them for a specific skill set to public speak and build their brand.”


Nevertheless, his expertise in working with professional athletes by providing highly supportive athletic growth and development opportunities to achieve success both on and off the field did not go unnoticed and then General Manager Reggie McKenzie and the Raiders came knocking in 2012.

Having been a former player himself, McKenzie knew the importance of the position and the value of having Winston help him transform the Raiders’ team culture that would further foster the success of players both on and off the field.

Across the NFL and player development community, Winston is known as one of the best to ever do it. The NFL commissioned The Winston/Shell Award in 2002, which recognizes the Most Outstanding Player Development Director/Program in the NFL. The NFL named the award after Winston and Pro Football Hall of Fame inductee Donnie Shell because the NFL considered them the indisputable leaders and innovators of Player Development in the League.

For Winston, his advice to players or anybody that wants to be involved in this business is to be willing to give yourself permission to look at your entrance simultaneously with your exit. It could be a long career, or it could be short. But the key is what are you going to be willing to do to stay and maximize every part of the middle of that as you can?

“It’s all about one’s willingness to make alterations to his or her own custom suit so it always fits right,” said Winston.

Winston has answered the call and found his purpose. He continues to be a great resource for those building player development programs across universities and other professional leagues.


“I know what I am. I know what my purpose is. When one finds their purpose, there is joy. I just want to share it. It all starts with trust.”

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