In this episode of the Draymond Green Show, host Draymond Green interviews former NBA guard and assistant coach Sam Cassell about his ongoing quest for a head‑coaching position. Cassell explains his coaching philosophy – the importance of knowing players off the court, balancing toughness with empathy, and tailoring "buttons" to individual personalities, citing Phil Jackson’s relationship with Dennis Rodman as a model. He recounts personal anecdotes, including a candid conversation with a struggling John Wall during his early years with the Washington Wizards, and his missed opportunity to draft Klay Thompson, which he believes would have changed the franchise’s trajectory. Cassell reflects on his varied experiences across different team contexts – from rebuilding young squads to contending with veteran‑laden clubs – and emphasizes his resilience, stating he will not give up on coaching. Throughout the interview, he stresses the value of relationship‑building with staff, maintaining a positive attitude, and his belief that his player‑respect and championship experience (four rings as a player) qualify him for a head‑coach role. The conversation ends with Draymond affirming Cassell’s potential and a brief promotional spot for DraftKings.
Chapters
Welcome to the brand new Draymond Green Show YouTube channel. Hit subscribe so you don't miss out on any of our content. Not only your journey through coaching, but your journey through what has been multiple times, to me as it seems, your name coming up in these head coach searches. Because like I said, I don't think you can get an argument outta anybody, if many people, if anybody, of where you stand as assistant coaches in the NBA, who you are, who you were as a player, your resume speaks for itself. And yet to me, these are my words, not yours. But to me, I think it's bullshit that your name just keep coming up because these guys don't be as proven as you, as players or coaches, not as respected, but for some reason, still not a head coach. What's it been like on these journeys, in these interviews, meeting with these owners, meeting with these general managers, and then ultimately falling short every time it comes around? Mm-hmm.
It's crazy, man. Like, hmm. It's been, it's a hard question to answer. You know what I'm saying? I have the experience. I know what buttons to push, get the best out of players. Can I be hard on players? Absolutely. Ask the guys that I have coached. Can I be hard on them?, but being hard on them don't mean you get the best production out of them.
Absolutely.
It don't mean you get the best production out of them. You got to know someone off the court to really understand them. I remember I was watching The Last Dance and I seen Phil Jackson and Dennis Rodman. They just vibing. And Dennis said, he took the time to know who I am off this court. He took the time to find out who I am off the court. I heard Michael Jordan say that about Phil. He took the time to find out who I am off this court. 'Cause on the court, I'm gonna be who I am. To find out who I am. So Phil knew the right buttons to push with Dennis Rodman, who was back then was a wild boy. You know what I'm saying? But when he came to work, he came to work. Yeah. You know what I'm saying? And as far as me not getting a head coaching job, I'm not giving up.
Yeah.
I'm not giving up. Good. 'Cause I love this shit. I love the game of basketball. You can ask anybody in Boston, when I come to work, I never have a bad day. Even though I might have a bad moment before I come into the office. You know, we all have families. You know what I'm saying?
Absolutely.
You know, I might have a bad moment, but I don't bring my bad moments to that basketball court, my players. 'Cause I know my players might have a bad day. So if I'm miserable, not miserable, if I'm not in the right state of mind and they not in the right state of mind, we not getting nothing accomplished. So I always have a great attitude around the facility. I go around every day, I speak to everybody with our traveling party, the trainers, the equipment manager. I speak to everybody. Draymond Green. Everybody, you know, what's up y'all? You can ask anybody on that staff because I understand that means something.
Absolutely.
You know what I'm saying? 'Cause I'm coming to a new staff and they don't, they really didn't know, they don't know who I am. You know, they heard and all of 'em say, oh man, Sam's a great dude. Knows the game of basketball. I know how to push and get the best outta players. You know what I'm saying? I'm just not, I'm not a yes me man. And that may hurt me. You know what I'm saying? I'm not a guy who, how I wanna put this, I'm a company man, but I'm gonna do things the way I think it should be done.
Absolutely. You know?
Absolutely. Somebody else, I'm not gonna, you earn playing time. You don't just get playing time. Not someone that's afraid of that aspect of me. You know what I'm saying? I'm just not giving up coaching this thing. I love it too much. You know what I'm saying? I got the respect of the players and I know how to get the best outta players.
Before we go, when you look at your journey, I truly in my heart believe that you will be a head coach in this league.
Yes, one day.
But when you look at your journey, and as you know, the drastic differences where teams can lie, a team can be super young with no experience, à la Detroit Pistons. And you could have a team that's getting older with a ton of experience, à la Los Angeles Lakers, Golden State Warriors. When you look at your journey, all that you've gone through, if you could pick and you said, I'd rather start with one of these teams that don't know much and help those guys get to the top, or I'd rather take one of these teams that could be right on the cusp on either side of the hill because— Good or bad. Yeah, good or bad. In 2022, They said we were on the cusp. They said we were on the wrong side of the hill. We won a championship, right? So on the cusp was on the cusp. Or would you prefer a team like that to where you can help push them to that championship right away?
It don't matter. It don't matter. I've been, I coached the Washington Wizards. My first 5 years in coaching. We won my first year, I think 18 games. Next year, 20 games. Third year, 24 games. And my fifth year there, we won 47 games and made it to playoffs. Won the first round. So I've been through every aspect of coaching. I seen the good, I seen the bad, I seen the real bad. You know what I'm saying? And as a coach, it humbled me. I just grew as an individual. I seen, I'll tell you a story. John Wall, his rookie year, he lost 8 games from high school to college, 2 years. He came to my room one day. I know he was in Cleveland. We 5 and like 25. Bad year. He knocked on my door. I said, "Oh, who? What's going on?" John Wall in tears, in tears crying. He lost 25 games, it ain't December yet. He lost 25 games, it ain't December yet. He asked me, say, "OG, is it gonna get any better?" And you ask any guys I ever coached, I'm not gonna lie to you. I ain't gonna lie to you. I ain't gonna lie to you. I said, I looked him in the face, I come on, I broke on him, I said, No. And guess what, J-Dub? I throw him a towel, went in the bathroom, throw him a towel, wipe your face, man. I say, "It's gonna be bad next year too." But we gotta grow.
Absolutely.
You gotta keep working.
Absolutely.
You gotta keep working. 'Cause if you don't, if you stop working with this, it's gonna get real, real bad. You the number one pick in the draft now. You the number one pick in the draft. And the city of DC, thinks that you're gonna bring a title to this city. Well, the owners did. I didn't think that. I didn't think that. I knew that he needed more pieces. And I'm telling you, the one that got away from us is Klay Thompson. I wanted them to draft Klay Thompson. I wanted the Wizards to draft Klay Thompson.
Mm-hmm.
Klay had the trouble with his background. With that old boy with the weed shit in college and shit.
Man, smoke the joint, man. Give it a break, man.
Like, but John needed a guy who was a flat out shooter.
Yeah. Yes.
When I seen Klay Thompson shoot the basketball, I remember I delayed the weight flip. I said, "Flip, that's the guy. That's what we need. Him right there. That's what John Wall needs." We drafted Jan Vesely. You know, I never knew him. I think Wesley was a decent ball player. He's no Klay Thompson. Not at all. John Wall needed shooting. So I saw, that's the best thing about me. I know what a team needs.
Yeah.
Been around this 32 years. You know, 4 champions. I won 4 championships. Been to what, 6 conference, 7 conference finals. So I know what winning look like. But I also know what losing look like.
Absolutely.
I know what losing look like. I look at the personnel, our team personnel, like, "Whew, this ain't gonna be good. This is not gonna be good." But I'm not gonna stop teaching. It's all about teaching. Any player I would work with, they say, "Oh man, OG know what the hell he talking about." All I'm looking for is a chance to show the world that I can coach the NBA ball club.
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