Here’s what NCHS ’73 grad Brian Sikorski—standout NCHS Rams football player and son of legendary New Canaan High School varsity coach Joe Sikorski—told me about a player just a few years older than he.
Though Brian Sikorski never played with Jeff Caldwell, he went to all of his dad’s games and loved watching the hard-hitting safety and linebacker.
“Jeff Caldwell was an assassin,” Brian Sikorski said. “Jeff Caldwell used to lead with his head and was one of the hardest-hitting players who ever played at New Canaan High School. Jeff Caldwell was the real deal. And if you got hit by Jeff Caldwell, you knew it.”
For this installment of “Ex-Canaanites”—where we reconnect with former residents to talk about their experiences here and plot New Canaan on the arc of their lives—we caught up with Caldwell at his Stamford home. A relative late-comer to New Canaan (his family moved here when he entered high school), Caldwell talked to us about what the town was like in the late-1960s and shared not only his personal story but some great anecdotes about well-known locals.
Here’s our conversation.
New Canaanite: Where were you born, Jeff?
Jeff Caldwell: Stamford.
No, actually, St. Joe’s.
St. Joe’s. Where Tully is now?
And when did you move to New Canaan?
So, what age were you at that point?
I had just turned 15.
So you moved there when you were in high school.
Actually, I went to Dolan Junior High School in Stamford, and they go through ninth grade. At that time they went through ninth grade. And when I moved to New Canaan, I was a sophomore and they had freshmen. So it was a little unusual.
So that was ’65 and you graduated when?
Whereabouts in New Canaan did your family move to?
Whereabouts on Jelliff Mill?
128. It’s about a halfway up. You go by the mill. I can’t remember the road that’s on the right.
Spring Water, maybe?
It might be. Might be. Maybe 100, 200 yards up on the left.
They’re gonna have a bridge replacement there. They’re going to close at least one lane for two years.
No kidding? Over the mill?
Well the mill is gone. They developed that whole property. I’ll show you a picture at some point, but there’s 10 condos there where the mill was.
No kidding? I remember when the mill was there and they actually built a new paddle wheel outside of it. Shortly after they put on that new paddle wheel, we had this ridiculous rain storm and the paddle wheel was going so fast it self-destructed. Just fell apart. It broke.
What was New Canaan like back then, in the mid-‘60s, the late-‘60s? What kind of town was it?
It was small. I mean, there was like one light. It was real quiet. It’s hard to explain.
You ever go back to New Canaan?
What do you go back there for, you visit friends or go back and visit certain places?
I go back to see my family.
Your family is in New Canaan still?
My two daughters, my ex-wife.
OK, so they live in New Canaan still.
They actually moved back from South Carolina. My daughters were born in Myrtle Beach.
Myrtle Beach. OK so let’s back up a little bit, then. You finish high school. What did you do after high school?
I originally went to college.
Albert Lee. How many years did you do there?
I only went for a half a year. I mean, I hated it.
You hated it?
I hated it.
And did you come back to New Canaan?
Who was waiting for you at home? Do you have brothers or sisters? Mom, dad?
I’ve got two brothers.
Older or younger?
One of each. My younger brother was still in high school. He played football with Brian.
OK. What’s his name?
So now tell me: You come back, you finish your thing, it’s the middle of the academic year. What do you do? You go to work?
What are you working at?
Working at Weed & Duryea.
Weed & Duryea?
Actually the first job I had was working at the convalescent home on Courtland Avneue.
What were you doing there?
I was an orderly.
You were an orderly there. Did you have a car to get into Stamford?
OK, and then you started working at Weed & Duryea at some point?
Exactly. I was driving trucks, delivering materials.
OK. And how long were you doing all this for, working locally?
Maybe a year or so.
And what did you do after a year or so?
What did I do? I became a lifeguard in the summer. And I ran into some guys and we moved up to Vermont. Ludlow, Vermont. To be ski bums. And that was in 1972.
So, ’72. Was it seasonal or did you stay up there year-round?
No. It was probably the worst winter in the history of Vermont. There was no snow, and when it did snow, the next day it would rain. And then it would get cold and everything turned to ice. You couldn’t ski.
Did you end up settling into a career?
Eventually. I went back to college. I graduated from Daniel Webster Junior College up in New Hampshire. Then I went to RIT [Rochester Institute of Technology] and took a job in New York.
What was your degree at Daniel Webster?
Just an AS.
Associates. It was a two-year.
Then you went to RIT. What did you study?
And then you went to New York City.
I went into the city. I worked for Barnes Press.
What year is this? What year are we talking now?
So, were you living in the city too?
No, I was living in Norwalk. I was commuting.
Commuting in from Norwalk. How long did you stay at that for?
Eight months. I hated the city. I hated the city.
So you came back to here.
Did you do graphic arts around here?
No. Actually I started painting.
And is that what you settled into for a long-term career.
Oh yeah. Thirty-seven years.
Who did you work for?
I worked for George Douglas out of New Canaan and then I worked for Rogers Painting out of Darien. Then I worked for—god, I can’t remember the name. Oh I worked for Burr Painting. They actually do roofing also.
B-U-R-R. Now they don’t do painting. They do roofing and siding.
Somewhere in there, you got married.
Where did you meet your wife?
In New Canaan.
She from the town too?
New Canaan High School graduate?
What’s her name?
How did you meet her?
Through a girl I was dating.
How did that work?
It actually worked out fine.
They stayed friends?
OK. What year did you get married?
Carol and I got married in ’83.
So you were well out of the city, well into the painting career.
Actually we got married in South Carolina.
What’s the connection to South Carolina?
I just decided to get out of Dodge. I was on my way to Florida and I ran into a friend of mine around Christmastime, and he said, ‘What are you doing?’ And I said, ‘Well, first of the year, I’m going to Florida.’
You’re up in the Northeast at this point.
Yeah we were in New Canaan.
You were married—
—No, this is before we got married.
I’m just trying to place the timeline.
I was married previously.
OK you were married before. So who was your first wife?
Her name was Blair.
Where was she from?
She was from New Canaan.
New Canaan, too. And how did you meet her?
I ran into her in a bar.
OK, so you married Carol in ’83. When were you married to Blair?
We were married from ’77. It was a bad marriage.
OK. You don’t have to say anything more about it if you don’t want.
No, we were together from ’77 until ’80. She moved to Richmond [Virginia], where her parents had moved, and that was in ’79 or ’80. And I actually met Carol after she had left.
Were you still married at the time she moved down to Richmond?
Where were you two living? You and Blair.
In Norwalk. OK, and then you met Carol, and eventually you divorced Blair.
I actually got the papers in South Carolina.
So tell me about South Carolina. You’re talking to a buddy, you’re up here, you say the first of the year, you’re getting out. At this point, you are dating Carol?
You’re dating. So she’s going to go with you wherever you go.
Well, that wasn’t necessarily the case. That was up to her.
OK, and you’re on your way to Florida—
—And I ran into my friend, and he said, ‘Why don’t you stop in to Myrtle Beach?’ I said, ‘Where’s Myrtle Beach?’ He said, ‘IN South Carolina.’ I said, ‘OK fine.’ So I drove to Myrtle Beach. And I didn’t leave.
For how long did you not leave?
What was it about Myrtle Beach that you liked?
It was so quiet in the wintertime. Now, it’s changed. It used to be a summertime resort area. Now it’s year-round.
So did Carol go with you or did she follow you?
No, she followed a few months later.
And then a little bit later you decide to get married.
And you get married down there.
And your girls are born down there.
And they go through, what middle school down there?
They were six and eight when my ex decided to leave.
And where did they come, back to New Canaan?
Yes she came to New Canaan, got an apartment there. And then she met some guy—nice guy.
She got remarried.
No she didn’t. She lived with him. His two sons, my two daughters, and they lived in a place in Darien. So my oldest daughter graduated from Darien High School. And then she left him and went back to New Canaan, and my youngest daughter graduated from New Canaan High School.
Oh boy. Big problems on Thanksgiving Day, I take it.
The Turkey Bowl? They care as much about football as they do a frog.
When did you come back up?
I came back up in 2002. April, 2002.
Did you come right to Stamford?
I came right to this house.
Right to this house? Who did you know here?
Your brother still live here?
No. He owns a small place in Ivoryton. Past Guilford?
Tell me about this house and you guys here. Are you still house painting?
You guys, you hang out, watch the traffic, chill out. How many guys live here?
Six guys. All single.
Tell me about you and New Canaan now. Do you go there for work? To hang out? Your ex is there, your daughters are there.
Exactly. The only time I go to New Canaan is to see my girls.
Tell me a little bit, because it sounds like you were a standout for the Rams. You played for Sikorski?
Tell me about coach.
He liked to think that he was a bear. But he was a big teddy bear. He was one of the sweetest guys you’d ever want to meet. But he’d act like he was a tough guy. He’d growl and make obnoxious noises. One of his favorite sayings was, ‘What are you doing? Watching the flocks fly over?’ You missed a play.
Where did you play on the field?
I played defense.
I was a safety as a junior and a linebacker as a senior.
Were you All County?
How did the team do your junior and senior year?
We were 7-2 when I was a junior, and we were 10-0 when I was a senior. We were the first team in the history of New Canaan ever to go undefeated.
So that was ’68.
Yup. We scored 412 points and only gave up 89, in 10 games.
You still in touch with anybody from the team?
I see Lenny Paggy [Paglialunga] every now and then, like when I go to a game.
Was Lenny Pags on the team?
Oh yeah. He was an All-State running back. All-County running back, All-State running back. When he was a junior, we were playing Andrew Warde, and Lenny scored 35 points in the first half, and on the last play of the half—he also kicked, he was the kicker, and when he kicked the extra point, somebody tried to take him out at the knees. It was the last play of the first half. And he reached down and helped the guy up and then nailed him.
Just socked him the face?
Oh yeah. So he got kicked out of the game. But that was the most points scored by anybody in a game, until the next week, when Bobby Valentine scored six touchdowns in a game. So he scored 36.
Exactly. But he played the whole game. Lenny only got to play the first half.
You know Bobby V?
Yeah, I do. Grew up in this town playing baseball with him and I played against him when he was at Rip. I loved football. I still do.
Who’s your team?
You ever head down to Boyle?
Oh yeah, as a matter of fact I was there for that championship game in the snow. I said, ‘You know what? New Canaan is kicking their butts. I don’t have to freeze any more.’ So I left at halftime. But I love the game. Can’t get enough of it.