During his 13-year NFL career, offensive lineman Will Wolford was on the losing side in three Super Bowls with the Buffalo Bills and two AFC Championship Games (with Indianapolis and Pittsburgh). By the time he retired in 1999, he'd given up on ever getting his hands on a winner's trophy. Then his luck changed in May 2003, when his 4-year-old colt Honor In War, a 24--1 shot, pulled away for a one-length victory in the Woodford Reserve Turf Classic on Kentucky Derby Day at Churchill Downs. "I wasn't much of a whiskey drinker until then," says Wolford, "but I do like Woodford Reserve now."
Wolford, 40, has come a long way from his days as a young man growing up in Louisville, when he used to sneak "jungle juice" (vodka and fruit juices) into the riotous Churchill infield on Derby Day. But those fun-loving experiences inside the far corner of the track inspired a new career as owner of his aptly named 3rd Turn Stables. Wolford has invested in more than 30 horses and currently operates a stable of six. None have been as successful as Honor In War, who has earned more than $725,000 in his three-year racing career. "Some of them have cost me a lot of money, and other ones have made up for it," says Wolford. "Last year worked out extremely well."
Much the same can be said for Wolford's career as a guard and tackle. After being selected for two Pro Bowls while playing for Buffalo, he was perfectly positioned in 1993 to take advantage of the NFL's inaugural year of free agency. The Indianapolis Colts made him the highest-paid lineman in the league at the time by signing him to a three-year, $7.6 million contract--more than Wolford could have imagined. "I would have signed for probably half that amount," he says.
Wolford, who has been married to his wife, Jude, for 16 years, and has three daughters (Grace, 11, Lauren, 9, and Bridget, 6), has spread the wealth across a variety of businesses, mostly in his hometown. He owns the Arenafootball2 Louisville Fire, which has led the league in attendance for the past two seasons, and Wolford Printing. He's also a principal investor in the Papa John's spin-off, Pizza Magia, and a part-owner of Fitness Systems, a Nashville fitness and equipment chain. This time of year he is busy at his high school alma mater, St. Xavier in Louisville, serving as an assistant coach and molding the next generation of offensive linemen.
"It's a big time commitment," he says of his ventures, "but sitting around and doing nothing for a living--it's not realistic." --Andrew Lawrence
A 13-year NFL veteran who played in three Super Bowls, Wolford owns a racing stable and an Arenafootball2 team.