Michael Jordan Once Handed $20K to Tracy McGrady After Losing Boxing Bet

Tracy McGrady got a first-hand look at Michael Jordan’s competitive spirit when betting against him on a boxing match.

Michael Jordan Once Handed $20K to Tracy McGrady After Losing Boxing Bet

Tracy McGrady on Michael Jordan (Image credits - Firstsportz)

In Short
  • Tracy McGrady won a $20,000 bet against Michael Jordan during a boxing match.
  • Jordan handed McGrady the cash after he successfully predicted the fight outcome.
  • McGrady expressed concerns about NBA expansion, stating there isn't enough talent for more teams.

Tracy McGrady was drafted into the league in 1997. Coincidentally, Michael Jordan called time on his NBA career after the 1997-98 campaign, ending it with his sixth NBA championship with the Chicago Bulls.

While McGrady was not able to go head-to-head against a prime Jordan, he did get to compete against the all-time great when he made his return to the Washington Wizards for two seasons. However, McGrady came from a generation that grew up watching Michael Jordan take over the basketball world.

Jordan, who was known for his accolades and achievements, was also known for his gambling habits. On the “Cousins with Vince Carter & Tracy McGrady” podcast, McGrady spoke about his experience of gambling with Jordan

We’re at the fight and I’m sitting directly behind MJ and Oak. Roy Jones Jr is a Jordan athlete. That’s why Mike is at the fight. They asked who I had and I got Tarver. Of course these two Jokers want to bet. Mike said put some money on it. I said I’ll do $20K. That was me talking out my a** I was nervous as hell. These two dudes want the money now.

Tracy McGrady on betting against Michael Jordan

It worked out well for the two-time scoring champion as he ended up winning the bet.

I’m praying to my lord and savior because I don’t got $20K on my right now bro and I don’t want to deal with these dudes. Tarver knocked that n**** out BOOM! WHERE MY MONEY. GIVE ME MY MONEY DOG! The whole world was lifted off my shoulders…. MJ called me over, we went and sat down. He’s like ‘you got me MF.’ He handed me a bag of $20,000 cash. I told him ‘I’m glad I won this cause I didn’t have that $20k to give you.

Tracy McGrady on Cousins with Vince Carter & Tracy McGrady

While Tracy McGrady was fortunate to win the bet as he did not have the money on him, it also goes to show Michael Jordan‘s competitiveness even outside the court. During his 15-year NBA career, Jordan cemented his place as one of, if not the greatest, players of all time and was widely known for his ultra-competitiveness and killer instinct.

Michael Jordan was an avid gambler even during his playing days and often went gambling with former NBA star Charles Barkley. A former NBA player, Troy Bell, once claimed that Jordan challenged him to a one-on-one contest for $10,000 and ended up losing.

Tracy McGrady does not want NBA expansion

Over the last few years, there have been talks of the NBA expanding after nearly two decades. While the idea was floating around, there were no major talks about it until recently.

The league is exploring the idea of adding two more teams in Seattle and Las Vegas beginning with the 2028-29 season. The response has been mixed from the NBA community. On the Cousins podcast, Tracy McGrady had his reservations regarding the expansion.

We got 30 teams. We don’t have the talent to be trying to start two more teams. Can we take away two teams and add two teams? I’m saying keep it at 30. The talent to me is down bro.

Tracy McGrady on NBA expansion

It is not going to be an easy process for the NBA if and when they do expand to 32 teams. A lot of changes will have to be made, and the NBA system will be restructured.

Carmelo Anthony leaves Tracy McGrady in disbelief with his Western Conference pick

There is no doubt that the Western Conference is highly competitive this season. The defending champions, the Oklahoma City Thunder, will be looking to go back-to-back this year, but face competition from the likes of the San Antonio Spurs, the Los Angeles Lakers, the Denver Nuggets, the Houston Rockets, and the Minnesota Timberwolves.

When asked about his pick from the West, Carmelo Anthony picked the Rockets, which left McGrady in disbelief.

Kevin Durant and his Houston Rockets teammates
Kevin Durant and his Houston Rockets teammates (Image via Rockets Wire/X)

Yes, they (Houston Rockets) can. Because we got a matchup now.

On hearing his pick, Tracy McGrady responded with a “Oh My Gosh…”

The Rockets are coming off a two-game loss to the Lakers at home. They are currently sitting at fifth place in the Western Conference standings with a 41-27 record.

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