My Love-ish Letter to Boston

Tim Hammill
40 Days to 40
Published in
7 min readOct 5, 2020

Note: I felt like I had to show Boston some love-ish after giving Los Angeles a three part love-ish letter (if you haven’t already, be sure to read Part 1, Part 2 and Part 3 of my LA trilogy).

If you’ve been reading along, you know that I lived in Boston from 1998 to 2004. But what you might not know is that my love for this town began in 1993 as a seventh grader on an epic class trip that included me wearing purple jorts and several classmates going to the Strawberries record store in Faneuil Hall to unknowingly purchase the clean version of Dr. Dre’s The Chronic.

Before we move on to the matter at hand, let me to take a short break to share a few questions I’m asking myself right now:

  1. Why did they all use their class trip allowance to buy something they could buy back home in Connecticut?
  2. Why does a clean version of The Chronic even exist?
  3. And why do I still remember this unimportant detail 27 years later?

All of it is befuddling me. Color me befuddled.

Now back to our regular scheduled program.

Aside from the aforementioned record store shenanigans, It was a very standard Boston class trip: Freedom Trail, Old North Church, New England Aquarium and Faneuil Hall. I’m guessing kids who grew up in the Boston area probably would’ve done this very same itinerary on multiple class trips. But for us Fairfield County kids this was the coolest class trip ever. We went to New York City the year before and we’d go to New York City the following year, we’d become blasé with the Big Apple. Boston, on the other hand was, to put it in terms I used in 1993, dope.

I was in love with Boston and knew I wanted to go back.

It took five years, but I made it back. This time with my parents on a tour of Northeastern University during my high school senior year spring break. I was even more in love. And so was my father. We were all sold on Boston and Northeastern. This city would be my new home.

The six-year period I called Boston home were pretty glorious, especially if you were a fan of the home teams. It was far less glorious if you were a fan of ambitious infrastructure projects or just enjoyed being able to drive and not get stuck in grueling construction-related traffic jams. This era included the tail end years of the Big Dig, the final year of nearly 100-year-old curse and the very beginning years of one of the greatest football dynasties that’s ever existed.

I’m not a Boston sports fan, but it honestly didn’t matter because I became a Pedro Martinez fan. My goodness, look at his 1998, 1999 and 2000 seasons and imagine being able to go to historic Fenway Park and see a lot of it up close and in person. Granted, I was usually sitting in the outfield bleachers, but still.

In 2003, Pedro and the Sox would lose a heartbreaker in game seven of the American League Championship Series to the hated New York Yankees. Seriously, as Mets fan I didn’t understand just how much Boston hated the Bronx Bombers until I got to hear my first “Yankees Suck” chant. The first I heard it was at Fenway, during a game against the Cleveland Indians. Not a Yankee in sight. That chant could break out anywhere, at a bar, in a cab, or I’m just guessing here, but maybe even during Sunday service. That’s what made Aaron Boone’s walk-off homer that much more painful, the team Sox fans spend so much energy despising looked like they were finally defeated. But no, Yankees win and go on to the World Series.

I will never forget what it was like to be in Boston the morning after that shocking loss, it was an eerie quiet everywhere you went even in my office which was unusually empty. This was my first job out of college, and I learned that day that a tough sports loss was a perfectly acceptable reason to call in sick in Boston.

A year later, the Sox would get their redemption and finally break the curse and bring home their first World Series since 1918. I wasn’t living in Boston during the playoffs of 2004, I had moved home to Connecticut in September to get ready for my move to Los Angeles just a couple months later. Even though I wasn’t physically there, it felt like I was there the whole time. With my Mets coming in at 71–91 that year, I think it was more than okay for me to become a fan of that Sox team, the lovable “Idiots” who made history and the impossible comeback on the Yankees in the ALCS, a comeback that culminated the evening of my birthday.

During my freshman year of college, the New England Patriots were seemingly this close to leaving Massachusetts and heading to Hartford to become… the New England Patriots. After Connecticut lost our beloved Whalers, the Nutmeg State was prepared to do whatever it takes to reel a major professional sports team into the state. In the end, it didn’t happen. The Patriots stayed in Foxboro, got a new stadium, a new quarterback and that’s it. Nothing else happened. The end. Ok fine, there was other stuff too.

I was in Boston for what was almost the team’s exit of the state and the start of the Tom Brady era, and the Patriots’ first three Super Bowl titles (2001, 2003 and 2004). What a dramatic shift in just a six year period. I was there for it all, and still do not like the Pats.

I even got to briefly meet the man who would go on to become the winningest quarterback in NFL history. Brady celebrated his first win as the Pats’ starting quarterback with a trip to Niketown, where I worked part-time during the school year. I’d like to say I knew he was destined for big things based on that brief interaction with him, but all I can remember about that day is all of the women I worked with swooning over him in his swooshes.

Even the Celtics, who had just lived through the dreaded Rick Pitino years, were good for the latter portion of my time in Boston thanks to the emergence of a young Paul Pierce. I got to watch in person the tandem of Pierce and Antoine Walker defeat the fresh-out-of-retirement Michael Jordan and the Washington Wizards in MJ’s fifth game back.

All of this winning by the home teams almost makes me forget about the things that make me don’t miss Boston. For the record, I do love and miss Boston but I definitely do not miss:

  • The high cost of living — You want me to pay how much to live with four other guys in three bedroom apartment in Mission Hill?
  • The long wait times for a bus — As I said in Part 1 of my Los Angeles trilogy, waiting 25–45 minutes for the 70 Bus in Cambridge on cold winter mornings was one of the main reasons why I left Boston for sunny LA.
  • The people who save their parking spots with lawn chairs, trash cans and whatever they can find to make sure they don’t lose the spot they dug out of the snow — I don’t blame the people though, there’s not enough spots in this city.
  • Overcrowding on the Green Line — We’re getting pretty specific here but the Green Line of Boston’s T is the line I spent most of my time riding. And by riding I mean standing up with dozens of strangers fighting to hold on to something, anything to avoid falling down at the trolley’s sudden stops. While we’re here, what’s the deal with all of those stops on the B trains? Can’t the BU (Boston University) kids walk a block or two? E trains over in Northeastern country are at least a 15-minute walk apart.
  • Moving Day — Who thought it was a good idea for everyone to have move on September 1st every single year? I’m guessing it’s the landlords who raise the rent every year to make you want to move somewhere cheaper, if you can find it.
  • Feeling old — With 50 colleges in one metro area, 23 feels like 43.

I picked a great time to be alive in Boston, if I were a Boston sports fan. But I also picked a gorgeous, walkable, diverse and great American city to call home. I’m still a sucker for a Boston movie, if I skipping through the channels and The Departed or Good Will Hunting are on, I’ll most likely watch for at least a few minutes. I take trips up to Boston a couple times a year even if it does make me feel old, because well, I’m turning 40, which is old enough to remember when we went to stores to buy CDs. But young enough to have to buy the clean version of The Chronic in 1993.

Tim Hammill is a communications professional in the nonprofit sector. He’s turning 40 on October 20, 2020. He’s writing about the final stretch to this milestone age in 40 Days to 40, a collection of stories, thoughts, reflections and whatever else comes to mind each day. In addition to writing a blog, Tim has also decided to donate his birthday to This Is My Brave, an organization he very recently learned about that brings stories of mental illness and addiction out of the shadows and into the spotlight. If you’d like to support Tim’s birthday fundraiser, go here.

Additionally, there are three other organizations that are close to Tim’s heart: Save the Children, Stand Up To Cancer and the Bridgeport YMCA. Click on each to learn more and to support their work.

--

--