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Making it, keeping it, growing it

How athletes stay rich: What we can learn

David Osborne
Nov 7, 2012 | 3:30 pm

It’s not uncommon to hear that professional athletes are broke. Sudden big paychecks often lead to big purchases and shortsightedness when it comes to the considerations for life after sports.

After all wealth doesn’t come with a coach or a playbook. In fact, many pro athletes set their spending patterns early on and find themselves working to keep up a good front with material items but have nothing invested away for the life-after-sports future.

Working with an experienced financial advisor and mentor early on in an athlete’s career can help that individual avoid the obvious pitfalls. Most recently ESPN’s “30 for 30” featured a segment looking at the subject of broke high visibility athletes. Everyone can learn from some of the pitfalls which include:

“In 1992, I was drafted by the Dallas Cowboys and I’d say 80 percent of my team from that year is now broke.”

• not having any guidance from a financial advisor early on and thinking that such guidance is only for the wealthy
• not fully appreciating the true value of money and assets when managed properly
• letting non-financial managers oversee financials
• spending before making or as fast as the money is made
• ignoring advice about saving for tomorrow. Phil Hanson, former NFL defensive end for the Buffalo Bills told his teammates, “A dollar saved today is 10 dollars tomorrow”
• feeling the pressure and obligation to financially support family members or friends or even making loans to friends and teammates in dire straights
• feeling overwhelmed by the financial pressures and expectations to the point of negatively impacting the athlete’s abilities and performance
• waiting too long to get a handle on the spending and making a lot of mistakes before figuring out there is a true need for managing toward a healthy financial future

Take Lomas Brown, former NFL offensive tackle and current ESPN broadcaster and analyst for example. He points out that when he was young he felt he would be playing the game forever and so mapping out his exit strategy wasn’t something he planned for. “I bought a car before I actually got signed by the Detroit Lions in 1985. I bought my mom a house and spent a lot more money than I needed to. When you’re young you think you’re invincible.” While Lomas was fortunate to have a longer playing career (eighteen seasons) and figured out his financial management in time, this isn’t the case for many other professional athletes.

Darren Woodson, the former NFL safety, is quoted in ESPN’s Athletes Being Broke saying, “In 1992, I was drafted by the Dallas Cowboys and I’d say 80 percent of my team from that year is now broke.”

So why is this happening to pro athletes? Well the truth is it isn’t just happening to pro athletes. It’s happening to successful people every day who are not accustomed to managing a windfall of money.

“The lifestyle is a gift and a curse. My third year in the league I had a Pro Bowl player ask me to borrow money. It can happen. You have to be smart with your money because the big paydays don’t last forever.”

Agents need to be coaching their rookies to have a financial advisor long before they make big money.

A good financial advisor will work with clients early on in their career to set up good habits and build toward future goals. Each athlete needs a senior mentor who has been there and appreciates that most athletes have a short window of playtime in their career and that’s when they need to capitalize on their savings and investments. Every athlete needs a financial advisor so they can clearly outline who they are paying and why.

A financial advisor should also analyze the potential for loss, the deprecation of assets, the impact a career-ending injury could have and how to plan ahead, as well as the impact that property damages and loss can have. Plus they look at some of the bigger legal liabilities a coach may have looming as well as the simple concern of overpayment on taxes because of poor portfolio planning and management.

The goal is for each athlete to have the A-team supporting them and empowering them toward a smooth transition into “life after sports.”

For many professional athletes, planning for the future may not be on their agenda. Playing the game is. However, it’s essential to have a financial advisor, a seasoned sports mentor and a game plan well before they head out to play hard and score big.

It’s easy for each athlete to get caught up and mismanage their income and assets whether big or small. Each rookie deserves to be educated on the good and bad of becoming wealthy fast. As Tutan Reyes, NFL free agent guard, points out, “The lifestyle is a gift and a curse. My third year in the league I had a Pro Bowl player ask me to borrow money. It can happen. You have to be smart with your money because the big paydays don’t last forever.”

---

David Osborne is the founder of Osborne Advisors, an independent private wealth management firm offering wealth management to high net worth individuals, families, estates and corporations since 1999. An extension of Osborne Advisors, Osborne Advisors Pro, is a sports wealth management offering created solely to focus on the unique financial management needs of professional athletes and coaches.

Securities are offered through SWS Financial Services, Inc., 1201 Elm Street, Suite 3500, Dallas, TX 75270, 214.859.1800, Member: FINRA/SIPC.

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Former Cowboy news

Ex-Dallas Cowboy Tony Romo placed on leave from CBS Sports after arrest

Associated Press
Jul 31, 2026 | 11:35 am
New York Upfront Partnership Event 2026 – Thursday, April 23rd
Photo by Noam Galai/Getty Images for Paramount
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Tony Romo has been placed on leave from his role as the lead analyst on CBS’ NFL coverage following his arrest last week on suspicion of operating a vehicle while under the influence.

CBS Sports announced Friday, July 31 that the former Dallas Cowboys quarterback was on leave “until further notice.” JJ Watt will join Jim Nantz and Tracy Wolfson as CBS Sports’ lead NFL team during Romo’s absence.

Romo, 46, was arrested July 23 after he was stopped while driving south on Interstate 43 in Wisconsin. According to the Milwaukee County Sheriff’s Office report, Romo performed poorly on field sobriety tests before getting taken into custody, booked and released.

He has a court date set for September 21.

CBS Sports’ announcement comes after citations released by the Milwaukee County Sheriff’s Office indicated an open bottle of an alcoholic beverage was found in the passenger’s side of Romo’s black Jeep during an inventory before it was towed.

According to the citations, police stopped Romo after he was seen passing cars in a gore area, which separates interstate traffic from cars entering from an on-ramp. Police said Romo questioned what a gore area was during the stop.

Body camera footage released earlier this week showed Romo telling deputies he had been coming from a golf course and was on his way “to visit grandma and grandpa” when he was stopped. A deputy told Romo he suspected him of being impaired because he had “red glassy eyes” and an “odor of an intoxicating alcoholic beverage.”

Romo went to high school about 35 miles from Milwaukee in Burlington, Wisconsin.

He has been the lead game analyst for CBS’ NFL coverage since 2017 after making four Pro Bowl appearances during an NFL career that ran from 2004-16 and was spent entirely with Dallas.

Romo remains the Cowboys’ franchise leader in career touchdown passes with 248. He held the franchise record for career passing yards (34,183) until Dak Prescott overtook him last season.

Super Bowl LVIII - San Francisco 49ers v Kansas City Chiefs Tony Romo has been placed on leave by CBS after arrest on suspicion of operating vehicle under the influence. Photo by Rob Carr/Getty Images

Watt joined CBS in 2023. He was an analyst on “The NFL Today” for two seasons before teaming with Ian Eagle on the network’s No. 2 crew beginning last season.

Romo wasn’t expected to have his first game until the opening Sunday of the regular season on September 13. CBS will air a preseason game between the Cincinnati Bengals and Philadelphia Eagles on August 28.

CBS likely will reveal its game assignments and announcer pairings for the first three weeks of the regular season in the next couple of weeks.

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