In this episode of the Draymond Green Show, Draymond interviews Golden State Warriors sharpshooter Klay Thompson about two major passions in his life: boating and his professional representation. Thompson recounts how his long‑standing dream of owning a fishing boat finally materialized in 2019 after a rehab period, describing the process of buying a closed‑cabin sport‑fishing vessel, taking boating courses, and the freedom he feels on the San Francisco Bay, Catalina, and the Delta. He explains how the nickname “Sea Captain Klay” emerged during that time, noting the irony of his first boat outing coinciding with a suspension and a Bay Bridge shutdown that forced teammates to pick him up by water. The conversation then shifts to the business side of basketball. Thompson reflects on his early representation by Bill Duffy (BDA/Wasserman), the personal connection through his father, and the pivotal moment in his sixth NBA season when he decided to explore new avenues for his brand, leading to a switch to agent Greg (Klutch Sports) around 2016‑2017. He discusses the emotional difficulty of changing agents, the desire for greater control over his brand, philanthropy, and future investments, and emphasizes that navigating these decisions requires tough conversations. The episode closes with a brief DraftKings sportsbook promotion by Colin Cowherd. Throughout, the tone remains conversational, enthusiastic about boating, and reflective about career decisions.
Chapters
Welcome to the brand new Draymond Green Show YouTube channel. Hit subscribe so you don't miss out on any of our content. 2019, 2020, right after this, Sea Captain Klay's born.
Yes, he is.
You're kind of away from the team doing your rehab, and then all of a sudden you come back around and you like, "Yo, y'all gotta come on the boat." Yeah. And we like, "What?" You like, "Yeah, y'all gotta come on the boat. Like, I got the boat up here. I got a boat." Mm-hmm. When you got the boat, was that always in your plans to get a boat or was that kind of like, I'm hurt, I need something else to do to kind of take my mind? Yeah. Like what was the process of that for you?
Oh, there was always a plan to get a boat. And believe it or not, there's a San Francisco Chronicle article from 2014 or '15 where I'm quoted saying, "My dream one day is to own a fishing boat." And it just so happened I had some free time. I got healthy enough where I was mobile again. In 2019, and I pulled the trigger. I got a big old sport fishing closed cabin boat, and, uh, everyone was— all my family, my friends were like, you don't need a boat, you don't know how to drive a boat. But I was like, I'm gonna take the courses, I'm gonna take all the steps, I'm not gonna make any shortcuts because I love the ocean. I love having that freedom, the freedom to go, you know, to Catalina or to freaking Sam's Anchor Cafe in Tiburon. There's just a whole new world out there when you get on the water. So I was doubted, but it happened, and I'm so grateful it did because I've seen a whole new side of the bay being able to get on the water and get out to Stinson or go up the Delta. There's just so many cool waterways and Now it's a lifelong skill I have as well. So it was always a dream of mine ever since I was a kid to own a boat and become a skilled fisherman. That part I'm not there yet, but I got the captain skills down.
I love it. My first time on the boat, I told y'all, my first time on the boat, I get suspended for coming and grabbing dude 'cause he was grabbing Klay. And ironically, I couldn't get to the Bay the next day or 2 days later. I was trying to get across to San Francisco to Chase Center. The Bay Bridge was shut down. Captain Clay E. Howson and CD came across the water to Jack London and picked me up.
That was a beautiful day.
Oh, it was a beautiful day. Pulling up to Chase. By the way, to go to work like that.
It's nice, isn't it?
It's fire.
It's nice. It's the best. Besides like getting shots up and winning basketball games, the best part of my day is really just like getting a coffee, going to Harbor and making my way down south to Chase Center. It's so beautiful, man.
Yeah.
It's the best.
No, it's absolutely amazing. A couple more questions before we get outta here. And you spoke about Jermaine O'Neal and teaching you about the business of basketball. And I've learned a ton through the business of basketball. Jermaine O'Neal was represented by Wasserman. Throughout his career. You are a representative, you are a Wasserman athlete as well. I've had 3 agents. My 3rd agent is Rich Paul, Klutch Sports, in my career, learning different things along the way and feeling the need for something different. You've had 2 agents in your career. What was a turning point for you when you decided, "Ah, I'm gonna go in a different direction"? Like what knowledge did you gain up until that point to where you felt confident enough to say, ah, I think I want something different at this point in my career in representation. What was some of the things that you picked up at that time to make you make a decision like that? 'Cause I feel like representation today, you get so many kids like, my mom gonna represent me, my dad gonna represent me, or this person. It's like, yo, there's a whole business out here that they don't have a clue what it means.
No, they don't.
And it kind of goes by the wayside. What was that for you at that time to make you make the decision who's, you know, now your current agent, Greg, that you've been with since 2000 and what, '18, something like that?
Yeah, '17 maybe, '16, around there. Wow, that's a good question. Well, I mean, I give credit to Bill Duffy as well. Bill was an incredible agent. He's been a super agent. He's been around the NBA forever. I mean, Bill was a freshman when my dad was a senior at the University of Minnesota. So that was easy for me. My dad been around the game so long, he's like, "No, no, no, we're gonna go with Bill." So I was like, "Okay, that's cool." Love Bill. And we did great things together. He's based out of Walnut Creek and he's still a really close friend. I know he's BP's agent, so I still get to see him and chop it up with him.
Mm-hmm.
But I think there came a time, you know, my 6th year where I was like, you know, we've done greatness, we've done great things together, but maybe I can explore some new avenues like, and just try and, you know, grow my brand, I guess. And I met with Greg and, I mean, we just kind of had similar thoughts of what the KT line could become or my interests, what I could grow those into, whether that be business or philanthropy. And that's the hardest part of this business is having to have those difficult conversations. And it, It hurt, like, separating with BDA, but at the end of the day, like, I was just thinking, like, um, I kind of want some more control over just, just, just a company just for me, in a sense, I guess. But it's still awkward to even talk about because I feel bad in a sense. Like, dang, it was never personal. Like, I never really meant knew what that meant as a teenager or college kid when someone's like, "It's not personal, it's business," 'cause, you know, emotions are involved. But that's really what it was. And, you know, I love Bill to death. I mean, that guy's like my dad's one of his best friends. They played college ball together. And it was just a tough switch-up, really.
And—
Uh— Had great success since, had some back then. And I don't, I'm not the most hands-on person, so helps when I have somebody in my corner who like will vet a lot of deals or bring to the table what they think is worthy of my time. And it takes a lot to get to that point. I wasn't really worried about the, uh, other ventures until we started winning and people started noticing us and we got some national notoriety. And then like, okay, I can kind of manage my time a little better. I've been in the league 5, 6 years now. I know what I want my future to look like. And that was that. And it was still— it was hard and it was a good lesson for what was to come if I do want to keep continuing to do investing and business after basketball, you're gonna always have to have those difficult conversations. And that was the first one in my career that was really like, dang, that was hard to do. And it didn't feel good, but kind of had to be done.
All right. The NBA season is in full swing coming down the stretch. Then we move right into the playoffs in April, May, and June. I can't wait. Spice things up with DraftKings Sportsbook, an official sports betting partner of the NBA right now. All you have to do is put down $5 and get $150 instantly in bonus bets. Pretty good trade-off. I pay $5, I get $150. North Carolina listeners, do not forget. Welcome to the party. DraftKings Sportsbook now live in your state, North Carolina. Download the DraftKings Sportsbook app. Takes 90 seconds. The code is Colin. C-O-L-I-N. Again, 90 seconds. Download. DraftKings Sportsbook app, put in Colin. New customers bet $5, get $150 back in bonus bets instantly. That is the trade. All right, the code is always Colin. The crown is yours.
