The Basketball Team Owner Who Tried (And Failed) To Ruin My Career

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I wrote about my experience with the Harlem Ambassadors ten years ago on my website.

The content is still there, unchanged. Read that after you read this.

Ten years ago, there were many fewer websites out there, much less social media, etc., especially concerning a small business like the Harlem Ambassadors.

So, googling the Harlem Ambassadors in 2009 would return as the top result. I’m still on the first page of Harlem Ambassadors search results even today, but no longer at the top — all of which was good for the Ambassadors, because I didn’t say all great things about them, which maybe hurt their chances of recruiting new talent (I don’t think so, but you never know).

I did (and will also do here) my best to be objective about the Ambassadors, sharing real experiences and real facts about what I dealt with in playing for them.

  • We traversed the entire midwestern United States (Colorado, Texas, Wyoming, the Dakotas, New Mexico, Arizona, etc) in a 15-passenger van. Google an image of a 15-passenger van. It does not fit 15 average-sized passengers, let alone 7-10 basketball players.
  • The players took assigned turns driving the van from state to state.
  • We stayed two-to-a-room in cheap hotels and motels. Super 8s and such; the kind of places where there would be a Super Walmart down the road.
  • You’ve probably never heard of this team I am speaking of. Well, The Harlem Ambassadors were like the Harlem Globetrotters (who you have heard of)  — but the Costco version. Smaller venues, lesser-known players (like me in 2006), 15-passenger vans, Super 8 motels for four days). You get the idea.
  • We did all the same stuff you may know the Globetrotters for: choreographed dunk routines, pulling the referee’s pants down for laughs (they would be in on the joke), grabbing 8-year-old kids out of the stands to dance, throwing buckets of confetti on fans.
  • Our normal opponents would be the local weather woman, the mayor of some small town, a charitable trial lawyer, some washed up ex-community college player who still played pickup on Saturday mornings. We would play one quarter of normal basketball, and three quarters of the dancing/tricks/family fun nonsense show.
  • Players would get fined for messing up a dance routine.
  • After our first exhibition game, one of my teammates, a Philly guy who, like me, had serious-basketball aspirations, summed up his/our current reality. I’m not a hooper no more. I’m an actor.

The Ambassadors structured their player contracts in such a way that a percentage of your money was withheld by the team, pending that you actually finished playing out your contract. I guess they’d had many issues with players defecting for better basketball opportunities.

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Being young and dumb, I’d signed the contract without fully understanding it; after our first time being paid, I had questions.

From the road (the Harlem Ambassadors were based in Littleton, Colorado, believe it or not) — we were in Texas by that point — I called the home office and asked some contractual questions that the receptionist told me the team owner would be best fit to answer.

Harlem Ambassadors owner Dale Moss came to the phone.

Dale answered my questions just fine, and did so again the next time we got paid and I still wasn’t clear where the rest of my money was.

Upon pickup up the phone on the second call, Dale chuckled and quipped, “Dre! I only hear from you when it’s about your money!”

While on those long ass rides in the 15 8 passenger van, I got to know a teammate whose contract was shorter than mine. G had a playing situation lined up in Mexico, a country where G already had years of playing under his belt, and after being impressed by my game during a day of normal-style pickup ball on one of our off days, G offered to help get me on a team in Mexico when my Ambassadors commitment was up.

Actually, G lightly strongly medium-level suggested that I maybe cut short my time with the Ambassadors, and just come to Mexico while the opportunity was warm.

This left me in a bit of a pickle.

On one hand, I knew that G was a player in Mexico, not a coach or GM or owner — while he could put me on, all that meant to me was that he could guaranteed that I’d get a fair looking-at by someone in Mexico who had power. That’s all that any player could do for a friend.

G didn’t have to say this in so many words, and I didn’t have to ask. Mexico and G were an opportunity, not a guarantee.

On the other hand, though, for me and my playing career, the Harlem Ambassadors wasn’t shit.

There were three, and only three, good things for me re playing for the Harlem Ambassadors.

  1. It was a paying job.
  2. It involved playing basketball.
  3. 1 & 2 meant that I didn’t have to have to do other paying jobs, like the overnight shelf-stocking gig I’d left when I’d gotten the call from the Ambassadors.

Nothing that happened while playing for the Harlem Ambassadors was gonna help my basketball future. The Ambassadors gig was nothing more than a stopover job for me and everyone else in that van.

So, non-guaranteed opportunity in a foreign country vs. wasn’t shit.

Which would YOU take?

Now, I told you about the shady way the Ambassadors structured their contracts, withholding money and such, as a deterrent for a player defecting — which sounds slightly reasonable.

But I looked more closely at the schedule and realized the real reason why they found a need for doing this.

After touring all these random, small, mountain time zone places, there was a two-week gap in our travel schedule with no games or commitments — which sounds like a great thing. The van would return us all (well, we were driving, so I guess we’d return ourselves) to Colorado, and we were free to do as we wished until the date our touring resumed. Two weeks without having to work? We call that a vacation.

But this “vacation” came with problems:

  1. We got paid by the game as private contractors, not as salaried employees. Two weeks without games = two weeks without income.
  2. Aside from the hotels we stayed in on the road, the Harlem Ambassadors did not provide housing.
  3. The Ambassadors did not plan to provide housing for this two-week off period. I know this, because I explicitly asked.
  4. In case you cannot tell from the context clues in this story, the Harlem Ambassadors weren’t paying me so much that these two weeks off would give me time to have fun exploring Colorado. By simple math, both options of A) Getting a hotel for two weeks or B) Flying home to Philly, then coming back to Colorado would leave me with less money than I’d arrived with.

So it was here that the Ambassadors often lost players, with, as you can see, good reason. This two week break would leave me in the red!

So off to Mexico I went.

I never got a chance to ask Dale why the schedule was structured that way, but he and I did communicate again.

About a year later, I was signing in Montenegro. The team there told me that I’d need to produce a letter of clearance from any prior teams that proved that I had no contractual commitments to any other team worldwide. Being ignorant of my own ignorance, I didn’t understand that what the Montenegrin team actually meant was any FIBA-recognized clubs (read: real, serious five-on-five basketball), which the Harlem Ambassadors were not.

I emailed Ambassadors owner Dale Moss, asking for such a clearance letter.

Dale, probably sore from the fact that another player had left his company/team for greener basketball pastures before their contract was completed, told me that if I would connect them, he’d be happy to let the club in Montenegro know how I had left his team in the middle of my contract.

I replied to Dale with an LOL and left it at that. We have not communicated since.

As I was considering what story to tell next for this post, I started googling past teams, and looked up the Ambassadors.

According to a Google ad purchased by the rival Harlem Wizards, the Ambassadors are out of business.

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Facebook hasn’t been updated since Spring 2017. Their website is a blank page.

This feels like going to one of my old schools of jobs and seeing that the building’s been torn down. Ashes to ashes, I guess.

Oh, and if anyone reading this sees or knows Harlem Ambassadors owner Dale Moss, please pass along a message — and make sure to tell him that it’s from Dre Baldwin:

I won. Bitch.


How did this experience — and many others in the randomness of pro basketball create the philosophy my business is built on today? I’ll show you in my book Work On Your Game: Using The Pro Athlete Mindset To Dominate In Sports, Business and Life coming February 20. Get all these bonuses for preorders now.

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