Photo by Muffy Aldrich
The Modern Guide to The Thing Before Preppy

Sunday, December 24, 2023

What is the Preppiest State?

 

A reader question:

Muffy, you saw The New York Times article that referred to Connecticut as preppy (and stuffy and sleepy) I'll bet.   I know we have talked about preppy towns on the blog, but what do people here think is the preppiest state, and why?

A comment of note:

Uhm, The Land of Steady Habits. Massachusetts is older and perhaps that ends the debate for many, but then we would have to go down the rabbit warren on flamboyant, Cavalier Virginia. Parts of the South generally belong in the conversation - they certainly adhere to tradition, I suppose - but they are of another genus altogether, sort of a post-Reconstruction Vineyard Vines genus; theirs is not a history readily claimed so everything has to stay superficial and comically light. This is not preppy; one’s personal history is core to “preppy” (or the the thing before preppy).

Back among the species, CT earns the title. Massachusetts’ loud history of radicalism - to this day - qualifies it as the crazy Aunt in Connecticut’s attic. Connecticut grew up and moved away, retaining the better lessons and traditions, eschewing all the drama and crazy notions. Too Cotton Mather and the Adams family are hardly on the Massachusetts scene today, replaced by money from somewhere else and largely due to the outsized growth and cultural influence of the now errant academic institutions that once did so much to define Massachusetts differently. CT has no academic core to tug it in faddish cultural/intellectual directions. Nothing tugs CT in ANY direction. Steady. Habitual. Industrious, constantly contentedly tinkering in the garage (and staying off 95).

Worth noting that the “preppiest” base in Connecticut is not where I live in Fairfield County but north and East of here, just to the west of Hartford up until you run into too many alien NYers in Litchfield County and then in pockets around New Haven. Hartford is what it has become, but that’s the sweet spot - and while, yes, they migrate to “The Shore” in summer, as they should, The Shore is still best understood as a summer colony (maybe - with Maine, of course - even the best one given who washes up on the Cape and Islands every summer these days). Fairfield County provides lots of ballast and that old necessity, money, to CT’s claim, but to restate the obvious it brings WAY too much New York with it. Still CT is NOT NY. It is its own place emanating from Hartford and New Haven first, as it always has.

Honorable mention belongs to New Hampshire, as another reader mentioned - maybe summed up best in the concluding stanza of Robert Frost’s “New Hampshire” the last line of which notes he is “at present…living in Vermont.”

An outstanding tangential read on America’s radically distinct regional origins is Albion’s Seed by David Hackett Fischer. Merry Christmas to all, and a thank you to our fine SWNE curators. 

54 comments:

  1. Maryland. I have this passage memorized from Lisa Birnbach’s official preppy handbook — it goes something like, "Lacrosse. By virtue of its very difficulty, it classically would not be considered preppy, except that lacrosse traditionally come from Baltimore, and Baltimore is very Prep." Yup—grew up there. Can confirm.

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    1. Lacrosse is a great game. Hockey, however, is the original prep back-and-forth-game team sport. Now many decades ago, the best from the town where I grew up often were recruited by the prep schools. “One and done” in those days meant a year of high school hockey, then off to play at a prep school. Back in the day there were far fewer rinks. But most prep schools had one. We played our pee wee hockey game at 5:00 Saturday morning. Then carpooled to a prep school to play another game. Before noon we were home. A quick lunch awaited us. Then it was off to the neighborhood pond with molasses cookies stashed in our pockets. We skated til dark with wind in the trees and a bonfire burning on shore. It was very atmospheric. And we felt it… Might anyone in the community know of
      Hobey Baker and where he went to school?

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    2. Hobey Baker, of course. Namesake of the top award in college hockey. Went to St. Paul's in Concord, but was originally from PA.

      Looking back at the old photos of him playing outside on natural ice at St. Paul's, I can't help but mourn the loss of so many outdoor winter sporting traditions as the climate changes. Hockey, along with nordic and alpine skiing, are all effectively dead as mass participation outdoor sports on natural ice or snow in most of New England. We keep them going by building more indoor ice sheets and setting up more snow guns every year, but it's clearly tenuous.

      New York winters are what Washington used to be, and Boston is now New York. Most of the downsides of winter without the glory of playing outside in the snow. In a turn of fate, perhaps Maine and Vermont will be the last bastions of preppy winter sports.

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    3. Thank you for bringing up Hobey Baker. More people should learn about him. He was the most superbly talented, modest, and gracious athlete; perhaps of all the 20th century. He was the very model of the Salt Water New England persona. After college he joined with other recent graduates, of all stripes, to play in all-star hockey games in the old St Nicholas arena on the West Side where I believe WABC tv studios now stand. These games were among the most popular social events of the season. Hobey was looked up to by F Scott Fitz. at Princeton. He was seen as Frank Merriwell come to life. He was a pilot in World War 1, the most dashing assignment of the war. He died, flying solo, in a crash in France shortly after the 11th hour of the 11th day of the 11th month. To this day there is speculation he was dead set on not returning to what he considered the drudgery of a desk job.

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    4. I also grew up in the Baltimore area. The National Lacrosse Hall of Fame and Museum is in Sparks, a small town outside Baltimore. Until recently, it was located on the campus of Johns Hopkins University in Baltimore. There are some very preppy parts of the city and suburbs with many prep schools, but I would say that Boston is a prepperier city, and Massachusetts is the preppiest state.

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    5. Talented athletes are a dime a dozen. Modest athletes are few and far between. You have the Mikaela Shiffrin, Bernie Williams and Wayne Gretzkys of the world (both now retired, alas). Gracious athletes are even fewer and far between. Is there one playing in the NFL, or the NBA? “Where have you gone Hobey Baker?”

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    6. Joe DiMaggio. Modest in his own way, I suppose. His heartthrob Marilyn once said to him, upon returning from an overseas tour to entertain the troops, “oh Joe you’ve never heard such cheering.” “Yes I have,” said Joe.

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    7. I live outside of Boston, and older people tell how they used to ice skate on the ponds around the area. Now we are lucky if the ponds even freeze all the way over. We've barely gotten even gotten any snow the last couple of winters, which makes skiing or snowshoeing much harder.

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  2. Massachusetts, of course. It’s where it all began.

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    1. Where what 'all began'? Jamestowne, Virginia was the first English settlement. We were here way before the Mayflower.

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  3. There are certainly preppy areas in and around Baltimore, Maryland, and lacrosse has long been a favored sport there. In fairness, Lisa Birnbach's prose isn't accurate about the origins of the game, nor was her preppy handbook intended to be factual - it has healthy doses of literary license and satire.

    Native Americans, primarily the Iroquis, Mohawk, Choctaw, and Ojibwe tribes, created the game that evolved into lacrosse. Mohawk and Iroquois were from Canada and Northern New York State, a little bit of Pennsylvania; Choctaw Mississippi and parts of Louisiana and Alabama; Ojibwe in the vicinity of the Great Lakes, both in Canada and Minnesota, Wisconsin, Michigan. The Tewaaraton award given to the top college male and female lacrosse players annually is a Mohawk word for the game we now call lacross.

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    1. Also copies from American Indians is the Ralph Lauren, the king of Prep look. has used many looks from tribal Indians to create his look.

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  4. The Commonwealth of Virginia

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    1. As someone who lives in VA, I wouldn't say that VA is the "preppiest" state. It's a large state, larger than most people think. And while there may be pockets of of "prep" (such as Middleburg and the surrounding "horse country), it's not how most people dress here, even in the northeast part of the state. Moreover, it's of the "southern" prep tradition, which, as a native New Englander, is a bit too pretentious and showy for my taste.

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    2. The Ancient Dominion is a strong candidate from the South. Horse country, Charlotteville, and Richmond are all strongholds of ancient families wondering what all these people (NOCD) are doing covering themselves in tattoos and hoodies.

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    3. Yes, the Old Dominion. Fox hunting, the Homestead, wine country, history, the Blue Ridge Mountains, Charlottesville, UVA, William and Mary, Washington and Lee, Hamden-Sydney, Sweet Briar, the Chesapeake Bay, sailing, golf, girls who say y'all, skiing (okay, not great)

      Not sure what "Southern" prep tradition means. oxfords, khakis, rep ties, blue blazers, tweeds, loafers, boat shoes, crew neck sweaters and the like are what we middle aged traditionalists wear here...I've been seeing more of the younger generation dressing properly lately, a good sign. I guess seersucker suits would be southern preppy.

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    4. As a Charlottesville lawyer and Washington & Lee alumnus with Virginia roots going back to the 1760s, I am pleased to agree that Virginia is a strong candidate for preppy capital. And as a Massachusetts resident for several years in my youth, I must admit that it has at least as strong a claim to the title. However, as with South Carolina down the map, Maryland to the north, and on up the east coast, the preppy or ivy style is now largely confined to enclaves and pockets in a sea of hoodies, athleisure, and giant sneakers, or so it seems to me. So let us be thankful for Charleston, Middleburg, Annapolis, Nantucket, Wiscasset and other spots where the culture has not been driven into hiding.

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    5. I agree with the lists above and would add: Old Town Alexandria, Lexington, Williamsburg, The Tides Inn, Hollins, Randolph-Macon, boarding schools, and an undying love of bowties.

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    6. Virginia has intensely prep "enclaves" (the foxhunt territories & Charlottesville) but overall is much more southern than preppy. The inverse would be CT. It's smarter to consider towns, versus states IMHO. Just look at Newport vs RI

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  5. The preppiest state is, of course, your state of mind.

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    1. Exactly! The question posed does not have an answer based in geography.

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  6. Connecticut is a funny state, with many very rich towns and many very poor towns. From what the article describes, the objective would be to make it more generic, not less.

    While it's probably too late for Connecticut to benefit from the upcoming national manufacturing renaissance, it would be a shame to see the state turn into a less dynamic version of the sunbelt in an effort to survive.

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    1. There was a time when even smallish Connecticut towns turned out household name consumer products. Think Seth Thomas clocks (Thomaston), Thermos (Norwich), or American Thread (Willimantic). This to say nothing of Gant and Sero shirts, Stanley Tools, Royal Typewriters and Sargent locks. We drove through one town after another in our 50’s and 60’s childhoods. My father would say, “this is where they make Keds sneakers… this is where they make Sunfish sailboats… this is where they make Armstrong tires” (they grip the road!) etc., etc.. Today it’s all gone, in one lifetime. Gone. Of course Connecticut still has serious manufacturing. Big time. But no one walks into a Wal Mart, or wherever, expecting to walk out with a nuclear submarine, a King Stallion helicopter or the engine that powers the F-35 fighter jet. Like everywhere in America the state is struggling to capture a share of the “manufacturing renaissance.” Is there enough of a legacy of skilled technicians for the state to actually rebuild its own versions of the “Made in the USA” brand?

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  7. Massachusetts, of course!

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    1. Ditto! Nantucket, Martha’s Vineyard, Boston, elite prep schools, elite colleges, most Volvos per square mile than any other state, and labsta! :)

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  8. Connecticut is the preppiest suburb of New York. Massachusetts is the preppiest state

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    1. Well said my friend, well said!

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  9. Re: outdoor winter sports. Fifty years ago I was at a Massachusetts prep school where the rink was outdoors, the modest ski hill abutted the school acreage (a walk-up, not even a rope tow) and the cross-country ski trails wound all around the school. Snow-shoeing through the woods down to the lake where students cobbled together lean-tos and makeshift stone fire-pits near their ice-fishing holes, cooked the fish , drank illicit beers and told tales. It was all delightful on sunny bright days but could be miserable on bitterly cold windy ones.

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  10. I never considered hockey as a preppy sport, too violent. Tennis as the peppiest sport. Connecticut as the peppiest State, but Massachusetts and New Hampshire for the most Preppy schools and Ivy League Colleges.

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    1. Absolutely yes tennis, and please don't forget sailing; inseparable

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    2. Well stated! Question, is pickle ball a preppy sport? Synonymous with club rights, reinvigorated tennis courts, and seemingly well ventured retirees. Friends, thoughts?

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    3. You’ll never, ever, see “violent” pond hockey.

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    4. Pro hockey can be violent. Yes. High school, prep school and college hockey is not. Hockey is the fastest and most creative team sport.
      It makes soccer and basketball, among others. look like their games are in slow motion.

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    5. YES, oh yes, I forgot Sailing.

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    6. Boston Globe once did a survey among youngsters who played four sports; baseball, basketball, football, and hockey. The question was, “which sport did they prefer?” 75% chose hockey. Why? You absolutely must be part of the action in hockey. Nobody gets stuck in right field or plays one of those positions where one never touches the ball. Size. Nobody is at a disadvantage in hockey because they’re too short or too small. Size is important. But in the end hockey is all about speed and skill. There’s plenty of room for smaller players. Equipment. Kids love equipment. Hockey has a lot of equipment. The stick. Everyone has their own stick. You can do whatever you like to it. Paint polka dots on it, if that’s your preference.

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    7. Pickle ball is the opposite of preppy. It is common and easy to play and it annoys the living daylights out of the neighbors. Crude. Also "everybody is doing it". Maybe "yuppie" but not "preppy". I have heard of another type of racquet sport though that I believe is popular in Florida (not jai alai) that is harder to play than pickle ball and is increasing in popularity. I forgot the name - believe it begins with "c" but that could be wrong.

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    8. You can add another reason; hockey is simply more fun to play. The “professional amateur” George Plimpton wrote several books about how he “played” for major league sports teams. He made the observation that football players after a practice would slowly trudge off the field, heads staring at the ground. After a hockey practice with the Boston Bruins he stood behind the boards with coach Don Cherry. Cherry had to keep yelling at the players to get off the ice. He turned to George and said, “it’s like a big kindergarten out there.”

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  11. Uhm, The Land of Steady Habits. Massachusetts is older and perhaps that ends the debate for many, but then we would have to go down the rabbit warren on flamboyant, Cavalier Virginia. Parts of the South generally belong in the conversation - they certainly adhere to tradition, I suppose - but they are of another genus altogether, sort of a post-Reconstruction Vineyard Vines genus; theirs is not a history readily claimed so everything has to stay superficial and comically light. This is not preppy; one’s personal history is core to “preppy” (or the the thing before preppy).

    Back among the species, CT earns the title. Massachusetts’ loud history of radicalism - to this day - qualifies it as the crazy Aunt in Connecticut’s attic. Connecticut grew up and moved away, retaining the better lessons and traditions, eschewing all the drama and crazy notions. Too Cotton Mather and the Adams family are hardly on the Massachusetts scene today, replaced by money from somewhere else and largely due to the outsized growth and cultural influence of the now errant academic institutions that once did so much to define Massachusetts differently. CT has no academic core to tug it in faddish cultural/intellectual directions. Nothing tugs CT in ANY direction. Steady. Habitual. Industrious, constantly contentedly tinkering in the garage (and staying off 95).

    Worth noting that the “preppiest” base in Connecticut is not where I live in Fairfield County but north and East of here, just to the west of Hartford up until you run into too many alien NYers in Litchfield County and then in pockets around New Haven. Hartford is what it has become, but that’s the sweet spot - and while, yes, they migrate to “The Shore” in summer, as they should, The Shore is still best understood as a summer colony (maybe - with Maine, of course - even the best one given who washes up on the Cape and Islands every summer these days). Fairfield County provides lots of ballast and that old necessity, money, to CT’s claim, but to restate the obvious it brings WAY too much New York with it. Still CT is NOT NY. It is its own place emanating from Hartford and New Haven first, as it always has.

    Honorable mention belongs to New Hampshire, as another reader mentioned - maybe summed up best in the concluding stanza of Robert Frost’s “New Hampshire” the last line of which notes he is “at present…living in Vermont.”

    An outstanding tangential read on America’s radically distinct regional origins is Albion’s Seed by David Hackett Fischer. Merry Christmas to all, and a thank you to our fine SWNE curators.

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    1. If oldest is the criteria, St. Augustine would like a word ;)

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    2. Inarguably CT, agreed. Incidentally it was NYC that originally “made” Virginia preppy, and NYC currently unravels CT. CT is the benchmark of prep. MA was the thing before

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    3. Dear Patsy,

      Yes, you are correct about St. Augustine. But it is a Spanish settlement - Jamestowne is the oldest ENGLISH settlement.

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    4. From @5:36am: "not where I live in Fairfield County but north and East of here, just to the west of Hartford up until you run into too many alien NYers in Litchfield County and then in pockets around New Haven. Hartford is what it has become, but that’s the sweet spot"

      There's occasional discussion here about preppy towns, but what the post above points out is that the remaining pockets of the older culture are now rural-adjacent.

      The towns and small cities of northwest CT and western Mass are often pretty grim. The nice old houses are often run down, subdivided into apartments, or both. Main streets are half empty, while the Walmart parking lot is full. If you drive through on the highway, that's about all you see.

      But back on the township roads - the ones that are about a lane and a half wide with no middle stripe - a little outside of town you still run across beautiful properties with a well maintained house and barn, stone walls restored, a neat woodpile, sometimes a solar array on the roof, and often an old Volvo or Saab parked in the barn half hidden by the F150 parked outside. These are the places that keep people with options from moving to the city, generation after generation.

      Beyond northwest CT, the Taconics and their eastern slope all the way up to Vermont have a high number of these sorts of places. The colleges in the area help, too.

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    5. You are correct, partially, well, a little bit, sort of, maybe, actually not really. Northwest Connecticut boasts but one Walmart. From our town it takes an inconvenient :45 to drive there on twisty backroads. So few bother to make the trip. The Walmart, at any rate, cannot be seen from the highway. Also we are thirty miles from the nearest interstate. So there are not a lot of highways from which to see “half empty” main streets and “run down” old houses. There, in fact, is but one four lane highway in all of Litchfield County. Look at the map. But we are nearly surrounded by prep schools. There are also plenty of paddle tennis courts, lakes for sailing, trails for hiking, organic farms (of course) and useful when it snows, there are two Connecticut size ski areas. There are, admittedly, few golf courses. Two have been proposed in recent years. Both requests were denied. Perhaps partly because, as one local noted, “golf brings in the riff raff.” There are, evidently, a lot of people sending and receiving old fashion handwritten letters. That must be prep. Or maybe people here just follow Ernest Hemingway’s advice. “Write letters… it’s such a swell way to keep from working and yet feel like you’ve done something.” There is one town of +/- sixty square miles (about the size of most towns in this area). The population is 1,500. They have three post offices. Somebody is doing some letter writing. There is also one town that has the highest per capita number of Citroen Deux Chevaux in North America. Is a Deux Chevaux prep?

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    6. @9:45am I was thinking primarily of the Hartford area that the poster above mentioned.

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    7. A Deux Chevaux is more bohemian.

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    8. Now - that begs the question. Is there a prep version of bohemian?

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    9. Nothing begs any question - because bohemian is the opposite of prep.

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    10. Might not a bohemian prep be someone who neglects to fasten the collar buttons on their OCBD ?

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  12. I grew up in Avon...we would always say: The Farmington Valley is a CT lifestyle, and Fairfield County is a fashion statement. It's proximity to New York doesn't help. Even in Darien.

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  13. I don't have a dog in this fight. I grew up in New Jersey along the coast. Spent early adult 20 years in DC and MD burbs. Did a post-Katrina stint in NOLA, followed by a few years in Atlanta with some seasonal stopovers in Palm Beach. Now back in northern VA with escapes to our hidden oasis in northeast GA. Preppiest?? Well it's as noted above, debatable. I just want clean air, clean water, peace and quiet, some great soil in which to garden, and a comfortable chair to read a great book--and nap.

    Best wishes all.

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  14. Connecticut Rules Preppy!
    I'm from Massachusetts, and once lived in New Jersey. There has never been a time when I thought either place was the preppiest.
    Preppy isn't just about style. It has a huge attitude attached to it. Nowhere else can that be found, IMHO, than in Connecticut.

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  15. Maine. Go to Bowdoin for 30 minutes. Nut said

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  16. I think any state that has an Ivy League school is in the conversation.

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    1. I understand your reasoning, but I doubt NJ is in the running.

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