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Theo Epstein on Brookline, field-goal contests, the horror of Game 6, and Boston sports memories

(Winslow Townson/USA TODAY Sports)

Up next in our continuing New England Roots series:  Theo Epstein, president of the Chicago Cubs, who shares his remembrances of growing up playing youth sports in Brookline, and rooting for the Red Sox, Patriots, Celtics, and Bruins.

Boston Sports Journal: What was your experience like growing up – did you have the typical experience of playing neighborhood pickup games, Little League and all before competing in high school?

Theo Epstein:  Yeah, organized baseball and soccer from a really early age. I think soccer was from kindergarten on, then Brookline Youth Soccer. I think I skipped T-ball and then got in at first level of Little League, and played both of those sports my whole life. We played pickup street hockey with the neighborhood kids and then this game called “Tenny Ball,’’ which was like stickball, but we used a tennis ball in this parking lot down the street from us. Those were the main sports – baseball and soccer. But I played a lot of pickup basketball and touch football, during recess and after school. And my (twin) brother (Paul) and I used to have these epic head-to-head field goal kicking contests. We would sneak onto Parsons Field at Northeastern and have field-goal kicking contests all day long, until we blew out our hamstrings. Paul had more leg, but I was probably more competitive, so it was a question of who could get the last kick in most of the time. And on a self-serving note, when I worked for the Padres, my friends and I had a competition and with a tailwind at La Jolla High, I once kicked a 53-yard field goal.

BSJ: What was the competition like with your brother?

TE: I think he only played a couple of years of organized baseball. We were on the same team one year, but then he stopped (baseball) and focused on track. But we always played soccer together; I never ran track and he stopped playing baseball. But we always played soccer together. We actually both suffered eye injuries while playing soccer, so our parents made us wear “rec specs,’’ remember the old “Kareem’’ goggles? We played travel team soccer and we were known as the “rec spec twins,’’ which I don’t think is how you want to be known, that’s for sure. We were on all the Brookline (youth) teams, then we played a bunch of indoor soccer at the South Shore Center in Hingham. We played there all the time and that was a lot of fun.

BSJ: How about your high school experiences in baseball and soccer?

TE: We were decent at soccer. I think we got into the Bay State League finals a couple of years, but we would always get our ass kicked by Wellesley or Newton North. And in baseball, (the teams) were horrific, truly terrible. I think I faced (Salem’s) Jeff Juden one time in a scrimmage and I remember being completely blown away. I couldn’t hit. I was a good field at shortstop and no-hit. And then pitched a little bit, but I was the kid who wouldn’t listen and spun way too many curveballs at an early age, so I had a good arm but threw too many curveballs growing up, so by the time I got to high school, my arm was hanging.

BSJ: What were the challenges of playing sports in New England?

TE: A not-so-fond memory was baseball in the spring, but during preseason, it was so cold and snowing out that all your practices would end up moving indoors. So, we’d be in the gym at Brookline High with these balls flying everywhere, off walls, guys getting smoked in the nuts. So your first real game of the year might literally be the first time you played outside because it was so cold. So you go right into a game situation not having seen live pitching outside. I didn’t realize how big a disadvantage that really was until I moved out to San Diego and saw the high school baseball out there. It was like a whole different ballgame.

BSJ: From a fan’s standpoint, what are your earliest memories of the Boston sports scene growing up?

TE: I remember watching Steve Grogan hobble around and people calling for Matt Cavanaugh to be put in the game (laughing) and then getting all excited about Tony Eason. Nineteen eighty-five was a big year. Those playoff games were epic. They were always causing turnovers. The whole town was captivated by the ‘’Squish the Fish’’ game. That was the Patriots team I was most connected to in my adolescence. And then the Super Bowl, I remember thinking they actually had a chance. They scored that first field goal and I remember thinking that we had it; it was in the bag. And then utter destruction, seeing the fear in Tony Eason’s body language as the pocket collapsed around him.

It was a great time for all of the teams. I remember when the Bruins finally beat the Canadiens (in 1988); I was really the only hockey fan in our fan, so I was the only guy in the house that would watch the Bruins game. I dragged people to Bruins game and watched them always lose to the Canadiens. It was a huge breakthrough when they finally beat them. The (Brad) Park overtime goal against Buffalo (in the 1983 Stanley Cup playoffs) was huge, but that was a few years before that. And I was always a big Rick Middleton fan, and then, Cam Neely. How could you not be? I was at the last game of the 1990 (Stanley Cup) finals when the Oilers won the Cup.

BSJ: Any Celtics memories?

TE: I don’t remember them being bad, so I think I caught on as (Larry) Bird came along.  I happily missed the (Sidney) Wicks-(Curtis) Rowe era and came along with Bird. I watched a ton on TV with my Dad, who was a pretty big Celtics fan. I got educated about the passing game. They made it look so easy; you were just basically waiting to see if they were going to win 70 (games during the regular season) and waiting for the Lakers seemingly every year. I remember the Rockets’ finals, with Ralph Sampson. I went to one of the games (in the 1984 finals), the one right before (Gerald) Henderson stole the ball. Then, they got so good that I got a little tired of it. I liked rooting for the underdog, which was easy to do with the other teams (in town). I kind of moved away from the Celtics, then got sucked back in with Reggie Lewis, being a local kid. I was a big Reggie Lewis fan.  And I remember Len Bias. I remember exactly where I was. We had Greek Day at school and we were outside on the playground, at a fair-type thing and word started getting around. It was just devastating.

BSJ: What do you remember about the 1986 Red Sox?

TE: Yeah, that whole season was incredible. We’d go to five-to-ten games a year, and watch all the others. I remember every pitch of Game 5 of the ALCS in Anaheim, watching the late innings. I saw (Dave) Henderson’s homer through my fingers, because I couldn’t bear to watch. I couldn’t believe they actually won. And then we went to Game 7 (at Fenway) when they won the pennant. Jim Rice hit a huge homer and they blew them out. And then we went to Game 3 of the World Series. That one didn’t go well. Lenny Dykstra led off the game with a homer that landed about 10 rows in front of me in the right-field seats.

BSJ: I think there’s a famous story about you and your brother, home alone, watching Game 6 of the 1986 World Series, isn’t there?

TE: Yeah, my parents were out at a dinner party for Game 6, so Paul and I are watching at home together, hanging on every pitch. We get to the bottom of the 10th and it looks like it’s over, we’re finally going to win. It was an out away, then a strike away. So we asked each other, ‘What do you want to do when it happens?’ and we decided we’d be in mid-air, untethered to the earth at the moment when the final out was recorded. So we got up on top of the couch, leaning against the wall, in this small den in the condo we grew up in.

We were up there for like 40 minutes. (It was) base hit, base hit, base hit. Then the ball goes through (Bill) Buckner’s legs and the winning run comes home, we both crumbled from the top of the couch and land on the ground, in agony, writhing, in disbelief. Then, the phone rings. We didn’t answer it, but we later learned it was my Dad’s cousin calling to tease him about what had happened.

I remember going to school on Monday (after the rainout on Sunday) and our math teacher said: “How many of you guys watched Game 6 on Saturday night?’’ We all raised our hands and groaned. Then he asked, “How many of you guys still think the Red Sox have a chance in Game 7?’’ And 90 percent of the hands went up, including mine. And he looked at us, shook his head and laughed and said, “You’re so young, naïve and stupid. They don’t have a chance in hell.’’ Then, when they had the lead in Game 7, I’m thinking about that, "Man, our math teacher was so wrong; in your face!" And of course, he was right and rubbed it in.

BSJ: How about favorite players?

TE: For some reason, I liked Quinn Buckner, probably because he looked like he wasn’t a good enough athlete to be on the court. He had a very low center of gravity but managed to be a pretty good player.

With the Bruins, as I said, Middleton and Neely were big, but I also liked, strangely, Vladimir Ruzicka (who had 39 goals in 1991-1992). He was really shifty with the puck. He never passed. He would just try to go end-to-end, and if he gave up the puck, he’d just smoke a heater and wait for the Bruins to get the puck back. No backchecking whatsoever.

On the Patriots, I really liked Andre Tippett. I liked the Weathers brothers, Robert and Clarence. And Mosi Tatupu. I liked the field goal kickers, too. I went to John Smith’s soccer camp, so I was a fan of his.

With the Red Sox, I was a sucker who thought that every athletic rookie who came up was going to be a Hall of Famer: LaSchelle Tarver, Chico Walker, Randy Kutcher. I was incredibly excited when Tim Naehring went up. I was kind of into the Latin shortstops – Rey Quinones, Jackie Gutierrez. I could hear him whistle all over the ballpark. I thought Carlos Quintana was going to be stud. And of course, Jim Rice and Dwight Evans. And Ted Williams, even though I obviously never saw him play.

BSJ: Any good Ted stories?

TE: Yeah, I got to spend some time with him in San Diego around 1995. We got to have a few minutes with him. My aunt’s husband was Fred Kaplan, who was a pretty well-known sports photographer he knew, so we caught up with him. My cousin Lee, gave Ted the nickname “Teddy Ballgame,’’ because he would ask his Dad, “Where are you going?” and (Fred) would say, “I’m going to go see Teddy at the ballgame.’’ And Fred told him about that and that’s how he became Teddy Ballgame. I still have hundreds of negatives and personal photos of Ted Williams that Fred had taken – at the ballpark, but also at home with his family. So that’s pretty cool.

BSJ: As a kid, how aware were you of the Red Sox’ tragic history and what became known as the curse?

TE: I was actually born in Manhattan and moved to Brookline in the summer of ‘78. So the Bucky Dent game was a pretty big deal, just because we had been in New York. But even in New York, my Dad had rooted for the Red Sox and persuaded us root for the Red Sox just because he was an iconoclast. But I remember after 1986, that really cemented that narrative and I was very conscious of it from that point forward.

BSJ: And the Patriots, who had never won either ... you went to Super Bowl XXI with (childhood friend and current Red Sox president) Sam Kennedy, right?

TE: Yeah, 1997. Sam and I went to Bourbon Street the night before and I think we both got concussions. The game was an afterthought pretty quickly.

BSJ: Now that you’re living in Chicago, how much do you keep up with the non-baseball teams in Boston from afar?

TE: Mainly through my brother, who’s still a big Celtics fans. (Danny) Ainge and (Brad) Stevens do an incredible job. This year’s team, in particular, is so much fun. I still root for them. I can’t believe what they’re doing without (Gordon) Hayward. If I’m flipping channels and the Celtics' game is on, I’ll watch that for a little bit. Paul knows the players 1-12, so I watch to be able to keep the conversation going.

BSJ: How about going to see any Boston teams when they’re in Chicago?

TE: I went to one of the overtime games in the Bruins-Blackhawks finals (in 2013). I was rooting for the Bruins. I still have a Bruins hat, a Celtics hat and a Patriots hat that I wear now and then, and a couple of shirts. I don’t wear Red Sox stuff, obviously; that’s put away in a memory box. But I still root for the other Boston teams, although I don’t follow hockey very closely anymore and my football rooting interest is pretty much wrapped up in my fantasy teams.

But I have so much respect for what (Bill) Belichick and (Tom) Brady and the Krafts have done. It’s just a model franchise. I’m trying to make my son (Jack, who’s 9) a Bears fan, but he remembers Boston a little bit and knows I used to be a Patriots fan and he likes a winner. So I’ve kind of rekindled a little bit of my Patriots fandom through him.

BSJ: Finally, because it’s Thanksgiving: any Turkey Day sports memories?

TE: My best Thanksgiving sports memory is actually the day after Thanksgiving, 1984. I was 10 years old, in our den, watching every second of (Doug) Flutie’s “Miracle in Miami’’ with my Dad and my brother. I can still see the veins popping out of my Dad’s neck as he lurched forward and yelled, “He caught it!’’ A Cinderella story, an unreal ending, and one of the best games of all time. Thanksgiving itself was usually reserved for watching Brookline High gets its ass kicked in football by Newton North, then pickup football games and field goal kicking in the afternoon with my brother and friends.