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I remember the day vividly. August 18th, 1992.

My dad finishes the sports page(well, really, the classifieds that were attached to it) and tells me to look at the front page.

It said “Larry Bird retires!”

Now, I don’t think I was really that shocked. He’d missed 35% of his games the past three years with that bad back, and they had just won that gold medal in Barcelona. After all those years of carrying a city on his shoulders, it was cool to see others carry him to the gold medal.

But see, it was time.

He knew it was time. He had a little magic left occasionally. Game 5 against Indiana in 1991 was the final deciding series win. He had his final triple double with a 49/14/12 after missing 40% of the year in 1992.

His final Boston Garden game was a near triple double with 14 assists.

Again, a little magic would come out from time to time. He knew it would disappear forever if he stayed. That is one thing Bird knew how to do that the vast majority of athletes don’t.

He knew when to go.

He knew when to go as a player, he knew when to go as a coach. He said it over and over he’d only coach three years…that players stop listening to a coach after about three years. I never believed him.

He had three division titles, three Eastern Conference Finals, and his final loss as a coach was in the Finals. I absolutely thought he’d be back to finish the job. Few were more competitive than he was.

Nope, he did exactly like he said. He left. Took a job in the front office. Won Executive of the Year, making it MVP, Coach of the year and Executive of the year in his career. Made the playoffs the majority of the time as an executive, but after a couple eight seeds, he retired for good.

Bird always had this uncanny knack for truly knowing when to go. We don’t see him shooting baskets on video or doing cool athletic feats at 60+ years old.

There is one video out there of him shooting a basketball in old age, and it’s him “missing” a free throw so that the players had to do more suicides. The video was shot from a great distance, like the guy knew Bird would hang him by his ankles if he was caught.

The shot had terrible form, on purpose, and he still almost made the shot. It was the smallest reminder that the guy would smoke any of us in HORSE to this day. We are left to hearing Paul George witnessing him hit fifteen threes in a row for the hell of it, then walking out.

That’s why he’s called Legend. Legends have stories you aren’t supposed to witness.

The problem is that Larry’s a rare bird. Many athletes have all kinds of trouble getting out at the right time. We just saw Evander Holyfield at 58 years old get bludgeoned by Vitor Belfort at an event where the highlight was finding out Donald Trump knows a ton about the history of boxing, and that was the only highlight.

A few months earlier, Roger Federer got smoked out of the quarterfinals of Wimbledon by Hubert Hurkacz in straight sets…6-0 in the third. Despite that, and despite having a business empire that’s going to take over tennis in a few years, he still doesn’t want to retire.

We have seen many a player try to pull off one more Jimmy Connors at the US Open in 1991. The results are usually the same. They have a five hour, five set, first round, and get smoked out of the second. We don’t need to see a legend like Federer do this.

You applaud a guy like David Ferrer leaving tennis by hitting his final running forehand by Nadal with a torn hamstring, but he’d always done that, and he was so low in the rankings that this was a first round match.

Also, Roger’s results after 35 far surpassed Connors anyway. He doesn’t need a Connors moment. His Connors moment was winning two straight Australian Opens far after his prime. We don’t need to see Roger drop to 174 in the world.

We see this from big stars, and we see this from athletes of all statures. They try to hold on. Moses Malone was an all-time great center, but he went twenty-one years, and it was easily a decade too long. He ended his career with five different teams and didn’t start one game for his final three years.

He also limped painfully up the court for his final decade, and ended his career with a 2.9 PPG average, a far cry from averaging 31 and 15 in one year. Even Bird ended his career at 20/10/7.

Look up any random player who had a cup of coffee in professional sports, and the ones that don’t become coaches keep lingering on in the craziest of places. It usually starts in Europe for basketball, or Japan for baseball. It usually ends with some long defunct basketball or baseball league that went bankrupt.

Football is even worse.

Former professionals will literally sell tickets in some outdoor league or arena league so that they can get enough clips to hopefully get a tryout somewhere, and with that tryout, they’ll hope to get in on the practice squad.

An NFL practice squad member makes $9,200 a week, which is $165,600 a year if you stay all 18 weeks. IF. There are no guarantees. One injury and someone else can take that spot. It’s all over.

This is why I’m spending a lot of time focusing on sports business. I’m interested in Kevin Durant’s venture WHOOP, I’m interested in Steph Curry’s business ventures, I’m interested in all those athletes. I am interested in an era where we might see less and less athletes go broke and try to hold on to their careers for dear life. David Robinson started a charter school for inner city kids twenty years ago. He followed that up with a venture capital firm, and he owns a couple Land Rover dealerships.

Junior Bridgeman started it all in the late 70s and early 80s by learning the business model of Wendy’s franchises and investing in Wendy’s franchises after he retired. He owned over a hundred Wendy’s and Chili’s restaurants before selling out in 2016.

He became a bottler for Coca Cola.

In 2020, he bought Ebony and Jet magazines for $14 million. He’s worth over $600 million now after never making more than $350,000 in a season. We need these stories. We need athlete success stories in this new era. We don’t need any more 30 for 30: Broke documentaries.

And most of all, we don’t need any more Ben Roethlisberger’s holding on and hurting their team.

That was then…this is now.



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