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Rip Hamilton Gambled on Half-Court Shots with Michael Jordan for Two Hours

When Bomani Jones and Dan LeBatard (to say nothing of Papi) have an athlete on Highly Questionable, the odds are astronomically high that they’ll get at least one quality story out of their guest. Yesterday’s episode with Rip Hamilton was no exception, as Rip provided excellent anecdotes on Rasheed Wallace’s sense of style, Carlos Boozer’s shoe-shine coif, his reaction to the Pistons drafting Darko Milicic over Carmelo Anthony, and the time he looked for Doug Collins to save him from a two-hour marathon of gambling on half-court shots with Michael Jordan.

Asked about his best Michael Jordan gambling story, Rip didn’t hesitate:

"“We actually had shootaround, and we were shooting half-court shots. We were actually shooting — I can’t tell you how much — for each shot that you make. I’m dogging him. I’m making every shot for the first 30 minutes. So Michael doesn’t want to quit, and you look at Doug Collins, Doug Collins is a coach that’s very respected, and when it’s time to leave, it’s time to leave. And I remember looking over at Doug and saying, ‘Doug, it’s time to go, you said, ‘Guys, be on the bus at 11 o’clock’ and it’s 11 o’clock now.’ So Michael was like, “No, we ain’t leaving.’ I’m like, okay, Michael, coach Doug Collins, who do I listen to? So I’m looking at Doug, giving him the eye, saying, ‘Doug, it’s time to go.’ [But] we kept shooting; we shot for two hours, and I’ll never forget it, because I was like an hour and a half into it, and I’m like, ‘I’m tired, I can’t keep shooting half-court shots.’ And we kept on shooting and kept on shooting, until he got even, and then we got on the bus, I looked Doug in the eye and said, ‘Come on, man, you’re supposed to be the coach.'”"

https://www.youtube.com/watch?v=07xEVLEhOsg

All of the details place this squarely in the 2001-2002 season — Rip’s third year in the league, and Jordan’s second-to-last.

Check out the full video for the aforementioned anecdotes; each and every one of them is worth your time. For now, we’ll leave you with a couple of double-takes. First, Bomani and Dan react to Rip’s comment that he considered going with the infamous Carlos Boozer Bigen hair style:

And, of course, the image that’s making the rounds — Rip’s reaction to the Detroit Pistons’ selection of Darko Milicic over Carmelo Anthony:

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