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Five Most Legendary Sports Agents

If you know anything about famous sports athletes, you know that there’s probably a very smart, rich, and powerful sports agent behind them. We’ve scoured the record books to find you the five most legendary sports agents the industry has ever seen. From the richest, to the most infamous and inspirational, we’ve got them all. The agents on this list will forever be remembered for their cut-throat negotiations, dedication, and heart.

1. C.C. Pyle (“Cash and Carry”)

You can’t have a legendary sports agents list without “Cash and Carry” making an appearance. He is known as the first modern sports agent and is known for earning unheard of sums of money per-game. Pyle earned his nickname from his legendary, record earnings, and he was also the founder of the very first professional tennis tour in the country. C.C. Pyle even founded the American Football League in 1925, beginning the competition for players with the NFL and starting what we now know today as a ‘professional sports agent.’

2. Scott Boras

Boras is a modern-day agent that has been (and still is) dominating the sports agent business. He currently holds more than $2 billion in active MLB player contracts and has been ranked as one of Forbes’ World’s Most Powerful Sports Agent. Before becoming an agent, he was an attorney who specialized in pharmaceutical law. In 1983, he negotiated “one of the largest contracts in baseball history, a $7.5 million deal for relief pitcher Bill Caudill.” Ever since then he has been agent to superstars like Greg Maddux, Kevin Brown, and Alex Rodriguez.

3. Gary Wichard

Many people may not know this famous person’s name, but know him better as the man who inspired the movie Jerry Maguire. His career was extremely accomplished and interesting; priding himself on forging close, unique bonds with each of his clients. Wichard described each one of his players as sons and was one of the most loyal agents in the world. He always represented each of his clients for the long haul, quickly becoming the most sought-after agents in the business. Wichard will be remembered for years to come for his remarkable player loyalty.

4. Don Meehan

Meehan is known as the most intimidating agent in the business. Alongside Pat Morris, they represent roughly 125 players. Sports Illustrated claims that “Meehan has dominated the industry of NHL player representation” for the last three decades, as a sports agent. He’s known for his stubbornness and has even threatened to sue players for libel. Anyone in the industry who knows Don Meehan knows that you don’t mess with him. He represents his players and defends his own with a serious ferocity.

5. Tom Condon

This legendary sports agent is known for his unique prospective. He is a former offensive lineman who tries to understand things from his player’s prospective. During the mid-80’s, he was the president of the National Football League Players Association and quickly learned he would be an effective agent. Since then he has negotiated record-breaking contracts and has represented an astounding six number 1 overall draft picks. Condon holds an impressive clientele list of 75 professional football players.

Professional athletes earn millions of dollar each year, and the agent behind them is responsible for it. Sports history has seen some of the most ruthless, inspirational, and effective agents possible. These five legendary sports agents have made their own marks on the industry in their own ways, earning their place in history.

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