December 31, 1969 Boston Tea Party, Boston, MA: Grateful Dead/Livingston Taylor/The Proposition

The Grateful Dead rose to prominence from the 1970s with financial anchors in certain strongholds that allowed them to tour in the points in between. The strongholds ensured their survival while the newly-conquered territory was subdued. In the early 1970s, for example, Grateful Dead concerts were a guaranteed success in Northern New Jersey, Philadelphia and Boston. From there, they extended their reach into New England, Upstate New York and the New South. It was a logical strategy, whether for a military empire or a touring rock band.

The Grateful Dead had mostly laid the groundwork for their 70s success in the 60s. They had played many New York Metro gigs before they solidified New Jersey. The band had played some famous shows in Philadelphia in the 60s, too, even if it took a little longer to conquer the state. But what about Boston? From about 1972 onwards, the Dead could count on Boston as a solid gig, with loyal fans and good ticket sales. In Deadhead lore, the fact that Boston was the site of the Dead's only New Year's Eve show outside of San Francisco or Oakland ensures Boston's status. 

Yet the Grateful Dead's New Year's Eve 69/70 show at the Boston Tea Party stands in stark contrast to the Dead's history in Boston. Boston was a hugely important rock city in the 1960s, yet the Dead had little to do with it until that New Year's Eve. Still--being late to the party doesn't mean you can't have a good time. This post will analyze how little is actually known about the Dead's New Year's Eve weekend in Boston, and how intermittent their previous efforts had been in Boston Metro. The Grateful Dead played three nights (December 29-31 '69) at the Tea Party, culminating in New Year's Eve. When the Dead played New Year's Eve '69, they played for promoter Don Law. Law was the Bill Graham of Boston, although he he had a much lower profile. But the Dead hadn't played for Law until just three months earlier. The Dead came to Boston late, but strong.

Warner Brothers released Live/Dead in November 1969

December 31, 1969 Boston Tea Party, Boston, MA: Grateful Dead/Livingston Taylor/The Proposition
Let me start by dismissing the main point. It's true that we have quality soundboard tapes of all three nights of the December '69 stand in Boston. In that sense, all of these shows are "known," in that many Deadheads have listened to those sets many times. But the shows are largely devoid of context. There aren't pictures of the band on stage at the Tea Party--if there is, please send them or link them--and save for brief reviews of the opening set on December 29, the only eyewitness accounts are mainly of the "I was tripping" variety. Because of the Dead's limited Boston 60s footprint, there is only a vague hint of how the Dead were perceived as similar or distinct from other contemporaries. Boston 60s rock music history is rich and well-documented, befitting a University town, but the Dead have little to do with it.

Because of the tape, and a general familiarity with Grateful Dead posters, plenty of 'Heads recognize the Boston Tea Party as a venue. When the Dead played New Years Eve '69, the Tea Party was at 15 Landsdowne Street, across the street from the outfield of Fenway Park. The Tea Party was Boston's foundational psychedelic venue, opening on January 20, 1967 at 53 Berkeley Street (at Appleton), in the South End neighborhood. Yet the Dead never played the original Tea Party. By the time the band played there, the Tea Party had moved a mile and half away to 15 Landsdowne Street, in the Kenmore Square district. Lots of music had happened in Boston in the 60s, but the Dead weren't the ones playing it.

The Grateful Dead New Year's show at Boston Tea Party were opened by an improvisational comedy troupe called The Proposition, itself a unique event. The Proposition, like Second City in Chicago or The Committee in San Francisco, had a little theater (at Inman Square, across the Charles River in Cambridge) and created improvised routines for every audience. The Proposition's claim, apparently, was that rather than doing unscripted but previously performed sketches, each Proposition performance was newly improvised based on suggestions by that night's audience. In that sense, The Proposition were an appropriate opener for the Dead, committing every night's chance to their skill at inventing art out of thin air.

The Proposition had about a half-dozen members, apparently, possibly on a somewhat rotating basis. I know of no tapes of their performances, even when they moved to New York in 1971. One of the cast regulars, however, was future Saturday Night Live player Jane Curtin. Curtin had dropped out of her junior year at Northeastern University to make a full-time go at the theater. Given the long, complicated history of SNL with the Grateful Dead, it is largely unremarked that Curtin opened for the Dead before the Blues Brothers ever did, and that the likes of Al Franken and Tom Davis would have been in awe when they found out. Did they find out? Curtin has never mentioned it, and I only figured it out by searching out the few archive postings from eyewitnesses. It's possible that the SNL crew didn't realize that Jane Curtin had out-Jerry'd them all.

In another break from Fillmore West orthodoxy, local folkie Livingston Taylor played between Dead sets. Now, even the Fillmore West and the Avalon occasionally had acoustic sets between acts, but not between Grateful Dead sets. Livingston Taylor was two years younger than his brother James. At this time, James Taylor had just released one obscure album on Apple Records in 1968. Livingston had been playing in the Boston area since 1966 and had at least a local name. He played in a bluesier style than his older brother. Livingston, managed by Don Law, would be signed to Capricorn Records, the Allman Brothers Band's label, and release his first (self-titled) album sometime in 1970. I'm not aware of any published recollections by Livingston Taylor of his time opening for the Dead (please Comment or link if you know one).

So: we can confirm three nights of fantastic music by the Grateful Dead. A future Television comic idol opened the New Year's show. Another opening act was not a complete unknown. Yet, the taped music appears seemingly from behind a closed door. This post will look at what little can be discerned from the Dead's strangely ineffective efforts to make it in Boston in the 60s, belying the fact that they hit the New England jackpot in the 70s.

The Boston Tea Party and Psychedelic Rock Music in Boston and Cambridge
Boston, MA is a huge city, and it has numerous important colleges and universities. Some of the most famous schools--Harvard and MIT, for example--are actually in the city of Cambridge, just across the Charles River from Boston, but broadly speaking they are all part of the Boston Metropolitan Area. The "Great Folk Scare" of the late 1950s started in Cambridge and Greenwich Village. Former Palo Alto High School student Joan Baez, a recent arrival (her Professor father had transferred from Stanford to MIT in her Senior year) came to notice in Cambridge around 1960. Folk music is outside the scope of this blog (for a great eyewitness account, see the book Baby Let Me Follow You Down by Eric Von Schmidt and Jim Rooney), but the early folk music explosion was essential to the rock music that would follow, and Cambridge was a wellspring.

The British Invasion landed hard on Boston and New England. The Boston and Cambridge area had numerous colleges--Harvard, MIT, Boston University, Northeastern, Brandeis, Tufts, and many others--and of course the surrounding suburbs had an infinite number of high school students. There were plenty of rock bands throughout New England inspired by or just emulating the Beatles and Stones, but that also is too gigantic a subject to even consider here. By early 1967, word had spread from San Francisco of another model, bands playing there own music in a big room where everyone could just dance, with a total immersion of lights and sounds. Boston was no backwater--they were going to have their own psychedelic ballroom, and the Boston Tea Party opened on January 20, 1967.

Initially, the bands that played at Boston Tea Party were just regional bands. The first headliners, for example, The Lost, were from Plainfield, VT. They had released a few singles on Capitol, and played various places, but they hadn't been out of New England. Their leader was Willie Alexander, mildly familiar to anyone who had too many records in the 1970s. For the second weekend, The Lost were joined by The Hallucinations, from Boston. Lead singer Peter Wolf and drummer Stephen Jo Bladd would end up in the J Geils Band a few years later. 

The Tea Party's initial profile was similar to the early Fillmore, with a predominance of hip bands from within driving distance. At first, the Tea Party was only open on weekends, a sign of a club finding its footing. Since it didn't sell beer, teenagers were welcome, a significant commercial point. Out-of-town bands only started to appear in late Spring, with David Blue and the American Patrol (April 28-29) and the Velvet Underground (May 26-27) from Manhattan. Still, the Tea Party was tiny. The official capacity of the Berkeley Street venue was 550. While that was no doubt periodically exceeded, for comparison, the official capacity of Keystone Berkeley was 476, and the original Fillmore about 1500. In 1968, the Tea Party added another fire escape and the official capacity was raided to 720, but even so it was just half the size of the Fillmore.

By the Summer of 1967, there were plenty of visiting bands: Peanut Butter Conspiracy (July 14-15, from LA),  Larry Coryell and the Free Spirits (July 21-22, Greenwich Village) and The Paupers (July 28-29, from Toronto). The first Fillmore visitation was by Country Joe and The Fish on August 25-26 (for a complete listing of known Boston Tea Party shows, see here).

The Psychedelic Supermarket
Not surprisingly, a competitor to the Boston Tea Party soon arose. The Psychedelic Supermarket was a converted parking garage, with grim acoustics to match. The official address was 590 Commonwealth Avenue, near Kenmore Square, but the actual location was in an alley backing on to Boston University. Owner George Papadopolis had run a coffee house called The Unicorn that had booked folk acts, and later electric bands, so he was a more experienced operator than the hippie-ish Tea Party team.

Initially, there had been a new psychedelic ballroom called The Crosstown Bus, in suburban Brighton, but it folded after a few dates. The Bus, however, had booked Cream for a week, and since their epic appearance at the Fillmore in August, the deal was too good to waste. Papadopolis apparently had been planning to convert the parking garage into a venue anyway, but he did so earlier to accommodate the Cream booking. The Psychedelic Supermarket had great bookings, but it's not remembered fondly by fans or patrons: the sound was lousy, the room uninviting, and Papadopolis had no reputation for generosity.

Lawrence Azrin, a former Boston disc jockey, has some biting reflections on the Psychedelic Supermarket

The Psychedelic Supermarket (located where Kix and the Nickelodeon Cinema in Kenmore Square are now) was a blatant attempt by George Popadopolis to cash in on a trend. He had run the Unicorn, a Boston folk club, for some years before deciding to expand in early 1968. Seating of 300 was in the lower tier of a garage that was completely concrete, except for the stage. Cream played a memorable gig there in February '68 [sic] not to mention Janis Joplin and the Holding Company. Stories of Popadopolis' financial finagling are a legend.. . groups would cancel contracts and leave because they would be paid less for long stands. The exposure was supposed to make up for the lesser pay!! One out of two bands would leave a gig after one set for various reasons and regular club-goers remember him raising ticket prices from $4.50 to $5.50 when he knew that a show was going to sell out.

The exceptional economic dynamic of late 60s Boston rock concerts was the multiple promoters. There was no Bill Graham figure dominating the landscape. Ironically, the Boston rock market was very robust, with college students and suburban high schoolers, and plenty of venues. Big touring bands could play lucrative college gigs or a variety of sports arenas and theaters. There were plenty of great rock concerts in Boston in the late 60s, but they were at numerous different places. 

The Grateful Dead introduced themselves to Boston by playing the Psychedelic Supermarket on the weekend of December 8-9, 1967. The band also fit in a Saturday afternoon show (December 9) at Clark University in Worcester, about an hour away. I'm pretty sure the band played another weekend at the Supermarket on December 29-30, but I have been unable to confirm that. We know they played Manhattan before and after Christmas, and we know they did not play the Fillmore New Year's Eve, as they were out of town. All signs point to Boston, but I can't find a firm trace.

The Van Morrison Controversy and Ill Wind were booked at the Boston Tea Party (at 53 Berkeley Street) for the weekend of May 31-June 1, 1968. The Ill Wind released a 1968 album on ABC called Flashes. Lead guitarist Ken Frankel had played in bluegrass bands with Jerry Garcia in 1962-63.

Boston Rock 1968
Rock music exploded in Boston 1968. Unlike many cities, the Grateful Dead played no part. The story is too long to tell here, but here are a few highlights:

• The original Boston Tea Party partners (Ray Riepen and David Hahn) added another one, Boston University student Don Law Jr. Don Law's father had been a staff producer for Columbia Records. Law Sr had produced Robert Johnson's only recording session in San Antonio, and he had run Columbia's country music division in Nashville since 1952, working with major Columbia stars like Johnny Cash. Law Sr had even produced Marty Robbins' "El Paso." Although Law Sr had taken mandatory retirement in 1967, he was still an independent producer. His son was just a student, but he had been born into the popular music business.
• The Boston Tea Party bet heavily on touring bands, particularly English ones. Throughout 1968, plenty of English rock legends came through; Procol Harum, the Yardbirds, Traffic, Jeff Beck Group, Ten Years After and more. Many of those bands would play Fillmore East as well as the Tea Party, as did some San Francisco bands like Steve Miller or Quicksilver. The Psychedelic Supermarket still booked shows, but the Tea Party was the place that everyone remembers.
• On March 15, 1968, WBCN-fm was the first underground rock music station in the Boston area. Don Law and Ray Riepen were the owners. Initially they broadcast out of a dressing room at the Tea Party. The most popular all-night dj was a jive talker called The Woofuh Goofuh. A true Boston legend--apocryphally, many came down from a long acid trip listening to Woofuh Goofuh jiving and playing blues and R&B records far into the night--his rein ended around December 1968. The Woofuh Goofuh was Peter Wolf, lead singer of the Hallucinations. When that band broke up, and Wolf joined the J Geils Band, he had to give up the dj gig. WBCN went on to become the dominant rock station in the region.
  
• MGM Records signed a bunch of up-and-coming Boston bands, like Ultimate Spinach, Beacon Street Union and Orpheus. MGM staff producer Alan Lorber, declared that Boston was the next San Francisco. Lorber coined the catch-phrase "The Bosstown Sound." The bands were actually pretty good, but there wasn't a "Boss-Town sound." The ad campaign backfired. Hippies were suspicious of anything promoted by "The Man." So some good Boston bands got overlooked because the rest of the country's hippies thought they were just hype. The Bosstown Sound debacle was a cautionary tale for record industry promotions of underground bands for the balance of the 20th century.
  

An ad in the March 14, 1969 Boston Globe for Theater events at The Ark on 15 Landsdowne Street. A rock show was held on the weekend (in this case Charlie Musselwhite and Elephant's Memory, Friday and Saturday, March 21-22)

The Ark, 15 Landsdowne Street, Boston, MA Winter and Spring 1969
For whatever reasons, the Grateful Dead were never booked at the Boston Tea Party. I myself don't think there was any complicated reason. I think the Dead shows in Boston in 1967 had been poorly attended, so there wasn't any impetus to book them. The band's two albums weren't exactly radio-friendly, even when WBCN-fm's underground sound came on the air. So the Dead never got booked. This would finally change in April 1969 when The Ark opened.

By early 1969, the Boston Tea Party was the flagship of Boston's underground rock scene. The Psychedelic Supermarket hadn't exactly closed, but it was only booking shows intermittently (by this time using the name The Unicorn, which had been the name of Papadopolis' folk club). About a mile and half from the Tea Party, neophyte promoter Charlie Thibeaux built a rock club over at 15 Landsdowne Street. The club didn't do well, actually, but it marked the beginning of making the Kenmore Square neighborhood into a leading music and entertainment district for Boston.

Although it is easy to google the Boston Tea Party, the Psychedelic Supermarket and The Ark with reference to the 60s, there is almost no systematic information about the period. Lots of people refer to the glory of 60s Boston, but the views are largely impressionistic, or based on somewhat vague websites focusing rather narrowly on posters. One of these days, not today, I will post my Boston chronology, but that is a mammoth project even by my standards. Certainly, there is no useful information about The Ark, so I will try and summarize that here. 

The Ark had opened on Friday, January 24, 1969. The model of The Ark seemed to be a Boston variation on New York's Electric Circus. I went into the peculiar history of the Electric Circus when I discussed the Dead's appearance there in 1968, so I won't recap it all here. Suffice to say the Circus had multiple stories, and was more of an "environment." Any performing rock band was just one element of the evening.

The Ark had three stories, and it is generally referred to in the Boston Globe as a "disco." There must have been a stage on one of the stories, but I assume the other two were for hanging out or dancing. In general, it seems that the Ark had a live band on Thursday, Friday and Saturday, and for the rest of the week they presented theater events on the stage. I know little about theater, but the performances seemed to have been pretty forward looking stuff: Bread And Puppet Theater, The SF Mime Troupe and so on. For music, there was usually a more modest act on Thursday, joined by a higher profile headliner for Friday and Saturday.

The two original owners of the Boston Tea Party had capitalized the club with just $850 in early 1967, and the venue was heavily dependent on volunteer labor. The Ark, in contrast, besides founder Charlie Thibeau, had 17 stockholders. Per the Boston Globe, they were "local doctors, university people and businessmen." The Globe said that 10 of the 26 employees of The Ark were full-time.

On The Ark's opening night, January 24, the headliners were the Los Angeles band Spirit, joined by The Bar-Kays, Otis Redding's backing band. No one in Boston seems to have noticed Spirit, however, since over at the Tea Party that weekend was the debut of Led Zeppelin (Thursday through Sunday, January 23-26), whose debut album had just been released. Those with too many records will note the irony of Randy California and Led Zeppelin debuting the same weekend in Boston. I have compiled a list of every booked music act at The Ark (forthcoming), and they included the Flying Burrito Brothers (March 6-7) and Taj Mahal (April 4-6) from the West Coast.

The Grateful Dead were booked April 21 through 23, a Monday, Tuesday and Wednesday. This in itself was a strange booking. Most "psychedelic" ballrooms weren't open except on weekends, although even the  Tea Party had started to add such dates. When bands were on the road, and had a few days off between weekends, why not play a few weeknight gigs, and take the door? Otherwise, they would be making no money. This was particularly true with English bands on the road, which is why you see weekday bookings at the Tea Party for UK bands in 1969.

The Dead were playing Clark University in Worcester again on Saturday (ultimately rescheduled to Sunday, April 20), and they had a big weekend booking at the Electric Theater in Chicago (on April 25-26). So they had nothing else to do, and of course no money--so why not take a flyer on an unknown, brand new psychedelic ballroom with an inexperienced promoter?

It is remarkable, and generally unremarked, how many chances the Grateful Dead took on the road with rookie promoters in strange cities. Whether Charlie Thibeau called the Dead, or the Dead called The Ark, the Tea Party didn't have a pre-existing connection to the band. In any case, even if the Dead weren't popular in Boston, they were still infamous, and for a new club, that mattered. So the band played three April weeknights in Boston.

The weekend before the Grateful Dead, the headliners at The Ark had been the Greenwich Village band Cat Mother and The All-Night Newsboys. They had just released their debut album on Elektra, The Street Giveth...And The Street Taketh Away, produced by no less than Jimi Hendrix. Both Cat Mother and Hendrix shared manager Mike Jeffery. Cat Mother was booked for Thursday through Saturday, April 17-19. The Grateful Dead's Monday-through-Wednesday booking at The Ark seems to have been the first weeknight music booking at the venue.

Since all three nights of the Grateful Dead performances at The Ark were taped and preserved, more or less in their entirety, Deadheads feel that they "know" these shows. And they do, up to a point. But an abstract listening to a live recording is just a single window. Were the shows crowded? Did the audience like the Grateful Dead, or were they just there for a party? Did people wander over from the disco, or did concertgoers wander out? It was a weeknight--when did the Dead start playing and when did they finish? Was there any opening act? We have the tapes--it's the Dead--but we really have no sense of what the shows were like.

David Lindley and Kaleidoscope played The Ark on June 20-21, 1969

What Do We Know About The Ark?
As is typical of late 60s Boston rock history, there is far less information circulating than you would expect. This effect is magnified by the fact that the Tea Party moved to the site of The Ark in July 1969. Many old Boston hippies referred to the Landsdowne Street Tea Party as "The Ark," whether because they forgot, or liked to show off that they knew the difference (in San Francisco, the comparison was referring to the Fillmore West as the Carousel long after Bill Graham took it over and renamed it). When Ned Lagin, for example, refers to having first seen the Grateful Dead at The Ark in 1969, we don't know if it was at the actual Ark (April 21-23 '69) or the Tea Party (Oct 2-4 and Dec 29-31 '69). This confusion riddles what few memoirs there are about Boston rock history.

An article in The Harvard Crimson student newspaper (published February 28 1969) by regular Crimson rock writer Salahuddin I. Imam entitled “Boston’s White Rock Palaces” described the original Berkeley Street Tea Party as 

a large square hall with a low stage. When it is full of people, as it often is, the performers seem very close to the crowd nearly submerged by it—which makes it all very warm and intimate—not intimidating as is the case in some circus-like arenas. The simplicity of the setup does mean that acoustics are virtually non-existent, but that is made up for by the immediacy and directness of the sound, which comes out quite powerfully amplified over the speaker system.”

The article ads “the crowds are hip, or perhaps too hip, because there is almost no dancing at the Tea Party. But then its probably just as well that people listen attentively to good music.

About The Ark, Imam said

The building and the whole of the main dance hall of the Ark, a newly opened club, is much more interesting than the Tea Party's box-like shape. Not surprisingly, the major emphasis at the Ark is on creating an elaborate and stylized fantasy environment, with the music as more a contributing than dominating factor. This effort at atmosphere is sometimes pursued a little too relentlessly but the overall result is nevertheless an interesting, sometimes fascinating, blend of modern multi-media techniques. 

The walls curve and sway, the floor winds round and round in ramps that dip and rise. Most of the ground is covered in thick blue carpeting expect for the main dance floor, which is to be painted in bright colors. 

With all this structural complexity there is much acoustic modulation. The sound has definite variations in texture (depending on where you are in the building) though the volume is never weak anywhere, owing to the incredibly expensive and sophisticated sound system that the club uses. Surprisingly the system sounds best when records are being played between sets. 

One area of the floor is ringed by tent-like walls and you feel like walls and you feel like you're in the middle of a growing plant. Another, a raised section, is entirely strobe lit, great waterfalls of light white light, and people dance as if bathing. 

EVERY INCH of wall space is covered with light shows of various kinds indifferent themes, with pictures ranging from ten foot high shots of Janis Joplin's singing face to Egyptian hieroglyphics. Fascinating things happen in isolated corners with the slides, but these shows are in fact all pre-programmed by computer; there is not the spontaneity and musical relevance of the Tea Party's light show, but rather a static grace. 



The groups that play at the Ark are not established rock groups, which is in line with the club's intent of emphasizing the whole experience--light and colors and sound rather than solely the musical. Occasionally one is able to catch a really fine group that has not yet made its name. One such was a group called Man, who did a remarkable, aggressive gig recently at the Ark. 

Dancing is not frowned upon at the Ark as it is at the Tea Party and most people do take to the floor at some tome or other, though one is slightly dwarfted by the cavernous height of the ceiling. 

The Ark caters to a different set of interests than the Tea Party and does it's thing pretty well.

July 1969: The Ark Merges with The Boston Tea Party
The July 10, 1969 Boston Globe reported that Boston's two major rock venues would be merging over the weekend. The Tea Party would produce their final show at the Berkeley Street location on Friday, July 11. Appropriately enough, the Velvet Underground were the headliners. Starting Saturday, July 12, all the scheduled Tea Party shows would move to 15 Lansdowne Street. The first headliner was Larry Coryell.

The Globe article makes it seem like a merger of equals, but I doubt that was the case. The Tea Party team was in control of the new venue. Ray Riepen was chairman of the operating entity (Environmental Arts Inc), while Ark founder Charles Thibeau was Chairman of the Board. Donald Law Jr was the actual General Manager of the new club. The implication of the article is that the 17 stockholders of The Ark have an ownership in the merged Tea Party organization. The Globe also points out that Riepen is President and a major stockholder of WBCN-fm, ultimately a far more valuable proposition than a rock club.

The article makes clear that Boston does not have room for two rock-only venues. In sum, the Tea Party had the underground credibility and the connections to booking touring English rock bands, but the club was too small. The larger Ark had not really been a success, even though some good bands passed through. The final concert at The Ark had been The Mothers Of Invention on Tuesday, July 8 (bootlegged and later officially released by Zappa). 

Once the Boston Tea Party took over the 15 Landsdowne site, I am unaware if any of the other features of The Ark were in use. Were there still 3 floors, multiple environments, a discoteque and weeknight theater performances? I am unaware of any such things, but reflections on the Boston Tea Party are fairly narrow, so it's hard to say. 

October 2-4, 1969 Boston Tea Party, Boston, MA: Grateful Dead/Doc and Merle Watson (Thursday-Saturday)
The Grateful Dead returned to 15 Landsdowne Street for three nights in early October. We have no tapes, so the concerts have disappeared in collective Deadhead memory, as if they didn't occur. A commenter on Dead.net recalls attending one of the shows, and that Doc and Merle Watson opened. Doc Watson was a huge influence on Jerry Garcia, particularly as an acoustic performer (just listen to Doc, and you'll see). The poster had the immortal Bonzo Dog Band as the opening act. Awesome as it would have been for the Bonzos to confront Garcia and Pigpen with the age-old question "Can blue men sing the whites?," it wasn't to be. The second US tour by the Bonzos was apparently a mess, and they only played a few gigs, not including Boston. So Don Law would have had to find another opener, and he couldn't have done better than Doc Watson.

The October shows must have gone well, because Don Law invited the Dead back for New Years Eve. He must have offered them good money, too. Now, granted, a place like The Tea Party, in a town like Boston, depended on hip prestige, so even in 1969, snagging San Francisco homeboys for a Boston celebration was going to stand out. 

November 23, 1969 Boston Music Hall, Boston, MA: Grateful Dead/Country Joe and The Fish/Pacific Gas and Electric (Sunday) 6:15 and 9:30 pm
Rather inexplicably, in between the October and December Tea Party weekends, the Grateful Dead were booked for a Sunday night show at the Boston Music Hall. They were scheduled for two shows, sharing with Country Joe and The Fish as headliners. The Dead (nor Country Joe) were not touring the East, so they would have had to fly out for the shows, and then fly home again. I had seen the ad for years, and had always assumed the show was canceled.

The Grateful Dead were on the ticket for the November 23, 1969 Boston Music Hall show, but they were replaced by The Youngbloods

I have since found out the show was not canceled, but the November 21 (Friday) Globe reported that the Dead were replaced on the bill by The Youngbloods. Given that the Dead would have been booked into the Tea Party for New Year's Eve by this time, Don Law could not have let this booking stand. My suspicion is that this was Lenny Hart's work. Booking a one-off show out of town, in contravention to another booking, only makes sense if proper management--as in "profitable" and "not-crooked"--were not part of the equation. 

Nonetheless, even though the Dead canceled out of the November '69 Music Hall show, it's still informative about the Boston rock market. The Boston Music Hall at 268 Tremont Street, in which the Dead would play epic shows a few years later, was much larger than the Tea Party, with a capacity of 4225. A promoter was bringing in two big San Francisco bands to compete directly for the concert dollar with Law's Tea Party. It was essential for Law to ensure that the Tea Party at least had the lock on being the coolest place in town, since it couldn't be the most profitable.

Tim Crouse's article in the Boston Herald, December 3, 1969

December 29-30, 1969 Boston Tea Party, Boston, MA: Grateful Dead
Fellow scholar Grateful Seconds found two brief reviews of the Grateful Dead's opening night in December. Tim Crouse of the Boston Herald describes what apparently was the writing of "Mason's Children," and mentions that it ended the first set. He also mentions that the band opened with "Mama Tried", and praises the fact of no opener.

Charles Martin's review of the Grateful Dead's opening set from the December 30, 1969 Boston Globe

Similarly, Charles Martin of the Boston Globe mentions that the concert began at 9:10pm with "a moving song" and the first set ended "The Mason Song." For those of you not familiar with the ways of 20th century rock critics, it is clear that neither writer stayed past the first set. It's possible that either of the writers likely had a deadline to meet and could not stay late in any case, but it's also possible that one or both may not have wanted to stay through the whole thing. So we know a little about the first set of the first night, but not much else.

New Year's Eve 1969-70, 15 Landsdowne Street, Boston, MA
We would like to say that the Grateful Dead's New Year's Eve show at the Boston Tea Party was the stuff of legends. But we don't really know that. Sure, the tape is great, but the Dead were killing it at the end of '69, so that in itself was to be expected. We don't really know if the weekend was sold out, if the sound was good, or what the crowd thought. There are a few hints from the Archive, typical of almost every Grateful Dead New Year's Eve show:

Howdy - Yes, I was there when this was played that very night. Good dear friend Marshall Goldberg was the sound engineer/designer for the Ark and the Tea Pary (when it was absorbed later on at the Landsdowne Street venue). The Ark was designed and built by Intermedia Systems Corporation, which, in 1969, did the logistics for Woodstock. I worked for them during this phase. Hi to Gerd Stern and Stuart Vidockler and George Litvin! Google those names for a ride through the acid-drenched '60s.
Livingston Taylor was on this bill, as was an improv group, Cambridge Light and Power, which oddly enough, was the previous tenant in what became Intermedia's new home base in 1969 - 711 Mass. Ave. Intermedia bought the only recording studio in Boston at that time - Petrucci and Atwell - and they are the name on some of the Timothy Leary recordings.

Great show. Went 'til sun-up. Everyone was dosed. EVERYONE. This includes Don Law, the manager of the Ark, who tried in vane to NOT get conditioned (someone got to his corked/sealed bottle of Mateus). The memory of him being escorted off of the stage as he asked the balloon-screeching audience "Have you all lost your minds?" Good entertainment there!

I just got a call from a friend wishing me a Happy New year and he reminded me about us going to this show 40 years ago! I did a search for it and found this sirte.... freakin amazing!

The show opened with Jane Curtin of Saturday Night Live fame way before she broke onto the scene nationally doing some wicked funny stand up comedy and Livingston Taylor (James's little bro) doing some bits of stand up between sets... I was tripping my brains out on Blue Barrel acid and he kept inhaling helium from a balloon and speaking which was way freakish and annoying at the time but funny in retrospect haha...

They played one of the most amazing moving rocking life changing shows till 4AM and I can remember everything from the exploding tie-dye paint splatter pulsating walls light show to the amazing vibe that only the Dead can create like it was yesterday! This is the Dead at their finest!

The MIT student paper (The Tech) from May 6, 1970, carefully noting that there will not be a free concert by the Grateful Dead

Aftermath: The Grateful Dead in Boston 1970-94
It took the Grateful Dead a little while to get established in Boston. After New Year's Eve, they only returned in the summer for a show at MIT. Being the Dead, however, they played a free concert at the school in Kresge Plaza, cementing their legend in Boston. The Kresge Plaza show took place during an anti-war demonstration following the Kent State disaster, so it memorialized the Dead in Boston consciousness. Any band could have played for free the afternoon of May 6, 1970, but it was the Dead who did it (as a footnote, the New Riders played a free concert in downtown Boston a few days later, but no one remembers that one).

The Grateful Dead returned to Boston regularly for the next few years, playing a variety of places for different promoters.  The biggest show was in Boston Gardens on April 2, 1973, where the show was promoted by Buffalo promoter (and now convicted rapist) Harvey Weinstein. Weinstein's firm also promoted the December 1973 Music Hall shows. I can't tell who promoted the June 28 1974 show at the Garden.

The Boston Tea Party had closed at the end of 1970, too small to compete in the growing rock market. Don Law went on to become a successful concert promoter in the Boston and New England area. Whatever exactly had happened on New Years Eve '69--which everyone seems vague about--it all paid off in a big way. Starting in 1975, Don Law began promoting shows by Jerry Garcia (April 6 by Legion Of Mary, for one) and Kingfish as well. When the Grateful Dead returned to the road in Summer '76, it was Don Law putting on the Boston shows at the Music Hall. To my knowledge, it was Don Law's company that promoted the Dead at every Boston show until their final stand there on October 3, 1994.

In 2009, the Boston Globe summarized Law's career:

After managing small acts in college and running the legendary Back Bay nightclub Boston Tea Party, he went on to either build, manage, book, or own everything from Great Woods and The Orpheum to the Worcester Centrum and the Providence Civic Center to the Cape Cod Coliseum, the old Harborlights, the Paradise, Avalon, and Axis. But in 1998, in a surprising move, he sold the Don Law Company for a reported $80 million to SFX Entertainment and signed a five-year management contract. Two years later, Clear Channel Communications bought SFX and named Law president of its New England division. In 2005, Clear Channel spun off its concert arm into a new company, Live Nation.

Just like the Bill Graham organization, however, the Grateful Dead were far and away the most profitable act on the live concert circuit. When BGP was sold, the news reported that while the Dead only represented 5% of the company's revenue, it was 25% of the profits. Don Law was hugely successful, and he had earned the trust of Garcia and Dead back when it mattered, but with the big guy gone, Law hit the bid and stepped aside.  Whatever happened on New Year's Eve 1969, it established the Grateful Dead in Boston for the coming decades, and anchored the business of the promoter who took the chance on them.