New England Roots

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?