Former Portland Trail Blazers General Manager and lead executive Bob Whitsitt had a storied, and occasionally tumultuous, run at the helm of his franchise. He took over the team in 1994 after having served with the Seattle SuperSonics in a similar capacity. He continued with the Blazers through 2003, overseeing the trade of Clyde Drexler, the acquisition of Rasheed Wallace and Scottie Pippen, and countless other moves.
“Trader Bob” has authored a book on his life as a professional sports executive. Game Changer: An Insider’s Story of the Sonics’ Resurgence, the Trail Blazers’ Turnaround, and the Deal that Saved the Seahawks will be available on October 10th, and it’s sure to contain plenty of interest to Trail Blazers fans.
This week Sam Yip of HoopsHype interviewed Whitsitt about the upcoming publication, asking about Whitsitt’s history, philosophy, and regrets. Here’s the response to the greatest regret Whitsitt had among the many trades he engineered:
Well, I could second guess every deal. There’s always something I can do better. There’s no question about it. I think the one thing I fought for at the time, and I was overruled, and I don’t mean that in the wrong way… at the end of the day, I’m an employee, I do the best I can do but owners ultimately make the final decision on everything. But I drafted a player in the first round in Portland. It was the 1996 draft, Jermaine O’Neal.
He didn’t bloom quite as quickly as Kobe did. They were the same draft but he was blooming and I knew he was gonna be a really good player. Around 1999 or 2000, somewhere in there, maybe 2001, we were in a situation where we were going to lose Brian Grant to unrestricted free agency and the owner just didn’t want to give him a new seven-year contract at the max because he has some injury history and I didn’t disagree with that. I wish we could have kept Brian but I just couldn’t talk them into a three- or four-year contract, which is as far as the owner was willing to go. He was able to get a seven-year max from Miami, so we knew we were going to lose him.
But at that time, rather than trade and bring Shawn Kemp in – which I really wanted to do – we traded Jermaine for Dale Davis, we would get a player a little bit more seasoned and probably can help us win a little bit more right now, but Jermaine was good enough that I knew if he got the playing time, and with Brian leaving, the playing time would open up. I wish we could have kept him. Then I would have had a young guy in place for the next 10-15 years. I don’t know if we would have won it that way, but I would rather keep a guy that I knew was on track to be an All-Star and was young as opposed to bringing in a guy in who only had a couple of years left in them. We traded Jermaine to Indiana, and I think he was a four, five, six-time All-Star.
So I get when you’re in the now-mode and the coach and everybody wants to have the little extra veteran piece. But sometimes you’d like to stay a little bit more [for the future]. This guy is pretty good, but more importantly, in three or four years, he’ll be really good. As a general manager that’s always wrestling with the now versus the tomorrow. So that’s one I wish I could have maybe done a little bit better and hung on to the younger player as opposed to bringing in a veteran player.
The rest of the interview is similarly detailed and well worth a read.