Ray Negron's Playball Weekly Blog

Dick Bily, The Boss’s personal John Wayne

Legendary New York Yankee owner George Steinbrenner had his own personal John Wayne. His name was Dick Bily.

The reason for the Boss’s adulation of Bily was because the Boss always admired those that weren’t afraid to try different things in life.

In the case of Bily, you’re talking about a guy who was signed by the Chicago White Sox and when things didn’t work out he joined the Air Force during the Korean War.

After his time with the Air Force ended he would move to Florida and start a career in the insurance industry.

Bily would become a giant in the insurance world and his path would cross that of one George M Steinbrenner. They would become fast pals and Bily would go on to do most of the Yankees insurance needs.

I always loved when Bily would come by the office because he always had a way of making the Boss laugh. Mr Steinbrenner could be in the worst mood in the world yet as Bily would walk into Mr. Steinbrenner’s office you would see the Boss’s spirits improve.

Bily always seemed to of had wild and crazy things always happen to him and the Boss always loved to hear about it. The stories would make for a wonderful sitcom. The Boss always thought that Bily’s stories were better than watching Seinfeld.

The best time that I ever had with the Boss and Bily was when we went to Hernando County to visit baseball’s greatest hitter Ted Williams. Williams had recently opened the Ted Williams Hitters Hall of Fame and Museum. After the ceremony, there was a little party. The Boss did not know how close Ted Williams was, a man that the Boss had great respect for and Bily was.

The Boss loved that Williams could really let his hair down around Bily and Bily could tell Ted his craziest jokes.

Bily is now 92 years old and mentally as sharp as ever.

I love talking with Bily because he always takes me back to a great time in my life when he was one of the very few people that could be real with arguably the most powerful person in sports.

Most people not related to the Boss were usually intimidated by him. He could give you that very hardcore exterior and if you didn’t know him like I did then he could scare the heck out of you.

Dick Bily always understood the friendship that I had with the Boss and always had one word of advice. Always be you and be real with that man and he in turn will always be loyal to you.

Nothing was further from the truth.

I miss the Boss every day and am grateful to still have the Boss’s personal John Wayne still here giving me and others positive words of advice.

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