Over four decades in baseball, Diamondbacks GM Dave Stewart has done nearly everything in baseball. He was a solid pitcher for 16 years, with 168 wins and a 3.95 ERA. Over four superstar seasons with the Oakland A’s, he collected 17.8 bWAR and four straight top-four Cy Young Award finishes. Upon retirement, he was a pitching coach and an assistant GM for multiple teams, and was a finalist to manage the Milwaukee Brewers upon Davey Lopes’s firing in 2002.
After failing to ascend to general manager in Toronto (with the Blue Jays instead hiring J.P. Ricciardi), Stewart formed a player agency and represented several stars, including Eric Chavez, Matt Kemp, Chad Billingsley and Chris Carter.
Years after Stewart had admittedly given up hope of ever being a big-league GM, Tony La Russa was hired to run baseball operations in Arizona and selected his former ace as the Diamondbacks GM.
Last week, we spoke to Stewart about his Diamondbacks team. This week, Stewart reflects on his career and his path to the big chair in this exclusive conversation.
You were drafted in the 16th round by the Dodgers in 1975, but you also had a ton of football scholarship offers, and played some pretty good basketball, too. Why did you choose baseball?
[Laughs] It was the sport that I was least likely to get hurt playing. There are obvious injuries that happen in baseball, but in football, even at 6’2”, 210 pounds, that’s not big enough to play the sport, for me. In basketball, there were some size restrictions as well. What’s great about baseball is that anybody can get on the diamond and show their skills. At the time, among the three sports, baseball was not my favorite, and probably not my best sport. But it’s just funny how things turn out.
Did you have any idea L.A. was going to convert you from catcher to pitcher?
No clue whatsoever [laughs]. Once I reported to [rookie ball in] Bellingham, Washington, the picture became clear what they were going to do with me.
You blossomed into stardom in front of your hometown Oakland fans, with four straight seasons for top-four Cy Young finishes. Meanwhile, your A’s teams made it to three straight World Series and not afraid to put somebody on their backsides to get there. But Oakland was under .500 in 1986, your first year in Oakland, and just .500 in Tony La Russa’s first full year as manager in 1987. When did the A’s develop their swagger?
We had a good group of players, [Mark] McGwire, [Jose] Canseco, Carney Lansford, Dave Henderson, Rickey Henderson. And you look at the pitching staff of myself, [Bob] Welch, Mike Moore, Curt Young; our rotation was good, we had Dennis Eckersley on the back end, and Rick Honeycutt and others in the pen.
But what really makes the team is the guy who leads the team, the manager. Tony was a great example of what we should be and how we should play the game. His message went through our clubhouse. We believed we could win, and when we stepped on the field, we were going to win. That all started with Tony and his coaching staff, and the things they brought to us day-to-day as players.
Since retiring, you’ve been a player agent, a pitching coach, in the front office, and even have gotten consideration as a manager. You seem to have your choice of baseball gigs. Why GM?
The general manager has the most impact on an organization and a franchise. I get the opportunity to pick the manager and put the players in place. It’s the biggest responsibility in an organization. I like that kind of pressure. I like being in that situation. I’ve won championships as a player, now I want to win a championship in the front office. In this capacity now, I want to be able to shape and form an organization, and build a tradition during my tenure.
You’ve been outspoken about the role of race in your goal to become a baseball GM. Was there ever a point when you thought it just wasn’t going to happen?
No, there wasn’t a single point, because by a certain time I definitely didn’t think it was going to happen. But the thing about baseball, especially at the upper levels of management, if you get the right person in the right position, it can affect your life immediately, as this did for me. Tony La Russa is a guy I’ve had a relationship with for over 30 years, and once he was put in a position where he could hire me, he did. If Tony would not have gotten his opportunity, I wouldn’t haven’t have gotten mine.
As you say, in many ways you learned how to play winning baseball under Tony, have been friends for decades, have discussed your futures in baseball together. Is it ideal to be working toward a championship in Arizona with him?
I know enough about Tony to say that our friendship had nothing to do with giving me the opportunity to do this job. But having a friendship makes it easier to do the job. Our communication is wide open. We feel free to talk with each other about anything. Most of the time our conversations are good conversations. Sometimes they’re not so good. We both have some fire. And that’s the great part about it, whether it’s a good conversation or a bad one, we walk out of the room united.
You were fresh-faced in 1981, winning your first title with Los Angeles. You were a pitching stud in 1989 when you won a second title, with Oakland. A few years later, you got a third in Toronto. Is there a favorite?
They were all good, because they were all at different points in my life. In 1981, I was just a rookie coming into the game, so I had an opportunity to win one right off the bat, which was great. I wasn’t of great impact to the Dodgers, but I was able to help them get there. In 1989, as you said, I was in the middle of it, and I made a difference in winning that World Series. In 1993 it was my last one, at the tail end of my career. I was on my way out of the game, contributing any way I could, but still having impact. I was ALCS MVP that year. But they were all significant and good because they were all different parts of my career and my life.