Memorandum . . To SAC, BOSTON Date 2/27/91 From SA Subject: WINTER HILL GANG IGB It is requested a control file be opened to administratively control incoming intelligence information pertaining to past and current members of the WINTER HILL GANG. This file will house information primarily concerning illegal gambling, however, if other information is developed it will be b6 maintained in this file as well for administrative purposes. b7C 7+ is recommended a new case be opened and assigned to SA Memorandum To SAC, BOSTON From SSA I Subject: m] (3E INFORMATION CONCERNING Date 11/8/90 (.7. Ga. x] (.3 i106 b7C 1:371} On 11/6/90] (Protect Identity) telephonically contacted urnis OWlng information: advised that ghadarecently opened an account[fu:i:f::j th a so urnished at the Sou .matenof.?ir?h BANK on furnis ed b? account number as Egg ?ocial Securitv Nw as In addition to the above b?D account, wstated 150 opened an account on 8/31/90 .nwonn address as 7" in addition to the informatiogtfufnijhed a Visaa-r?w+ individual by AKA anj Date of BirthTEf:ff?f] Social Security Number open ount on 10/23/90 at the bg his address as Vise that his records ""b7D re ec that individual. not be di ?iBoston (92A-2557) Q/Qmm; (2) {wt 1'4 was listed as an LCN associate in 1986. could no furnish additional information concerning this The above information is singular in nature and should sseminated without prior approval of the Writer. 1* He ?Ib6 - fb7c 645 95/ BS 192B-BS-54085 :j i; . b7D On December 21, 1990,] Iprovided the following: I lin addition reviously .bg married to he has was also 4 marrie 0 al who reportedly "ives and . Thev had a son called b?D 0 uses -- - is 21-22 years or age,' and oes imina inc 1 a es care also has two dau-hters another He a niece of . b? The daughter by that marria last name unknown ied and who is living b7D with on' atl ep one is a white ma 1 iSource is of the impression that fo? Ihas the financial support of her father. Source is of the If opin' tI wou member, aside b6 fromth:EEj to be in touch withI I b7c b7D Ih ns at home, Ia. - 17, who attends age 7. His Wlfe. has a brother, wh b6 b7c I I commonlv knonm as I I it: mn'r'b'i? at the 213713 5435 {5'35} ,1 Complaint Form FED-71 (Fiev. 2-13-86) NOTE: Hand print names legibly; handwriting satisfactory for remainder. Facts of compla?in?t book/(Co wt? (ae/ 3&1?th Ac?: in) t0 t'lf No,qu Git/(31744 icdds?fj? (CS Meow away? (62 NM sigma. Do not write in this space. 345 2153if} .b7C Indices: Ell Negative El See?below b6 Character of case - I I 5 Complainant E/Protect Source 2106 b7C Co IUVUIVVH Personal [Zl/l?e/lephonic Date?'?me I Address of subject I I Race Sex Height I Hair 8 We 5 4 Alluwm 930059}; =5 2: Age Weight Eyes Complexion Social Security Number la, .3 Female a ?5 (70 (D Scars, marks or other data ?9 6/ Z, VIVU (WON I '07/ (Mbn?/ @an fd?NU/ Ni fa.wa etc/3123c .aQe 0 60L, 1 Minds?944.? MKQUJU) 0.9, 5 NW Nor-C, 5 ?p31? ?1 BS 182B-BS-55853 MJszea b6 b7C b7D wed thatI?LI aka [in ooking to "sel 1y "?at is owned jointly by] Iii?fa] I Inr?gddition source advised/{hat a FNUI I the 307?: b6 b7D 1/ Ib? Md bizc My Memorandum . . . To SAC, BOSTON (182B-BS-55853) Date 4/24/91 OH From SAI I amka: RENTER HILL GANG IGB On 3/6/91 this case was opened and assigned to writer. Case was opened as a means to administratively control incoming intelligence information pertaining to past and current members of the South Boston based WINTER HILL GANG. This file will house information primarily concerning illegal gambling, however, if other information is learned or developed concerning the WINTER HILL people, and their associates, it will be maintained in this file as well. All 0?3 Agents are requested to direct any and all information relating to the above criteria to this case file. 0013M NE: C-3 AGENT 5/ M33 amm (16) [39 -mliiw r? i ?inhafo I I "1 ou??ui [30? Memorandum . - . To SAC, BOSTON (183B-BS-55853) Date 5/8/91 From SA I :136 Subject: WINTER HILL GANG IGB a; .On 5/6/91 an indivldual to has provided reliable rmiormium?the that a new/contact location Pm? and is NE I [35453? 55251; Cm. 1 )Ql A a BS 182B-BS-55853 I RHW:jea 1. be On May 8, hdvised of the followingb:C information: b/D Regarding Ihas been doing La?kal br 0 dbaI - b7C introducingl I I b7n I I (who resides atl I formerly married to La,? . I Imay have some contacts withI _u 4; I "telephone be r??-1l in prison years,ago, elped himvb7C ._6ut7__T I several vears ago. b7n an I I Recrardinontenti on I that I I knew- b6 b7C b7D ccor 1nd 0 Source had no knowledge of drugs/being an0 ve 1n ese ants, and was not introd1 contacts. had an individual names in ew ork City, at one'number In 55753 ?7 suns?) BS bf 2. bic 4r? Regarding a Federal Fugitive, source knew nothing cuts. There is ve: tle discussion, if any, a relatives regarding Source char ed quiet, unassuming, and bright ib6 individual. ivowe a became a fugitive that he would b7C never serve a av in ?ail. was ite osite in character b7D when compared to who source characterized as loud, obnox1ous, a conman. Source did not believe would hang ar "wise guys" Source felt, howev at would be the one in 1V1 family member that won contact. Source stated that never talks about and according to family members, has never attended any family gatherings. J/,x I l?haa?t?* da?ghters by] and I lis married tol W91 who?f?cently move eir business, A, .unsure if I b3 was at par. LiUipdnL in that. DusirrES'r' b6 b7C still legally married 573 who is known by the to whom to, is One child by nick name 0 Ib6 although neveg?nWLs an had a son name le I Ialsb Has a daughter by the name ofl by another father. I land I Ch mother is still living. Her name i 5 years old, residing at C30 husband is deceased. BS JRB:jea l; On June 5, 1991, gambling on various professional and colleqiat advised as follows: Irecently lost Sports ey is owed to two bookmakers: ?ran collecting the made to pressure relationship to contacted I'll I for the money, due to However no a gem}? b7D b6 b7c b7D events. aka about will bebZC close ?b?D {23 i Ji'll? '83 55393, if . a . ?9 JUNZ i 1991 lr i BS 182B-BS-55853 RBC:jea l; 1:36 lb7C orks'atl i_l I1 b7D On June 25, 1991, advised SA I Ihe knows of a bookmaker name has al 19?. swmeijmsonlnamedl Imh) . 336 Efif3eLEa1e, to bookie I -7 as Kph) I b7D ItelenhO? Ihas grandchildren living inl lfrom a previous marriage. ADMINISTRATIVE: i 3 Reg' Motor DOB address has a re01Ster to him. RMV lists a b6 I b7c I 133-53? /0 a? 1' in?: uf i126 137:: Ma I I 0 01,: 4m. 1:2. @3521 NE 7/97 mm TO: SAG, Boston (18?;NK;?g?ggk?rp) Eb67/03/91 TC.) 11 - 4; ,rb-gsyg- we SUBJECT: HOUSE ODDS 00: BS RE: Newark teletype to Boston dated 7/1/91. PURPOSE: The purpose of this memo is to document information obtained on 7/2 and 7/3/91 relative to captioned matter. RECOMMENDATIONS: This memo contains no recommendations. DETAILS: Dn Tuesdav. 7/9/91. +he luv-5+gr- CA b6 b7C 13713: The cw, andl 1:56 :b7C b7D l?J FD-35O (Rev. 5-8-81) I 6 deals of Whitey cronies By JONATHAN WELLS When reputed mob boss James J. ?Whitey? Bulger and Kevin J. Weeks joined two friends at Lottery headquarters last week to cash in a $14.3 million Mass Mil- lion ticket. it wasn't the ?rst time the two got to- gether to consummate an unusual business deal. Bulger, a convicted bank robber and alleged leader of a South Boston- based crime organiza- Turn to Page 14 (Mount Clipping in Space Below) .27 ?i The sharp i (Indicate page, name of newspaper, city and state.) BOSTON I-IERAID BOSTON MA Date: 8/ 4/ 91 Edition: SUNDAY, ME THE SHARP DEALS OF CRONIES Character: or Classification: Submitting Office: Indexing: in; "-40 BCEJHELEE: AUG it 5 ?res ?bile 0% it i :tvm .. 139.. es ?$5253 a m. m* From Page 1 I tion, and Weeks, who has no criminal record, have been par- ties to complex, and at times bi- zarre, transactions for years. On the same day in August 1988, the two long-time friends bought adjacent units in the new Bigelow Court Condominiums on West Fourth Street in South Boston for $150,000 apiece. Two years later, within four months of each other, they sold their condominiums Weeks to a Boston Police sergeant for a modest loss and Bulger to a South Boston real estate broker for a $36,000 profit, despite the depressed condominium mar- ket. Records show, however, that Bulger already had drawn a much larger profit from the property before it was? redeve- loped into the six-unit Bigelow Court complex. In October 1985, Bulger bought the lot from an- other longtime pal, Kevin P. O?Neil, who also goes back many years with the band of~Lottery winners. O?Neil sold the Bigelow Court parcel to Bulger for $30,000. Bulger flipped the property a year later to Barbara A. Buckley for $150,000 a shrewd swap which landed Bulger a tidy 500 percent profit. Joining Bulger and Weeks at the Lottery last week to divide up the winnings was Patrick J. Linskey',? whose brother, Michael Real estate records detai a, DEAL: James 'Whitey? Bulger, above, sold, bought and resold condomin- ium property at 327-329 West Fourth .St. in South Boston, right, for considerable profits in recent years. C. Linskey of, Hanover, pur- chased the winning ticket at the South Boston Liquor Mart. The store is?owned by O'Neil and a partner, and Weeks is the manager of record, where he has had a state Lottery ticket franchise since 1986. A few years later, on Dec. 8, 1989, Bulger and Weeks partici- pated in a strange series of real estate transactions which fed- eral authorities have alleged were a charade to create a phony record of legitimate in- come for Bulger. At the time, Bulger owned a one-third interest in 295 Old Co? lony Ave, site of the South Bos- ton Liquor Mart, with Weeks and Mary I. Flemmi, the mother of reputed Bulger crime associ- ate Stephen ?The Rifleman" Flemmi. Weeks testified under oath be- . fore the Boston Licensing Board in January 1989 that it was the profit motive that prompted him to sell two one-third interests in the property to Bulger and Flemmi in May 1986. However, Weeks went on to say the building's assessed value was $40,000 and he sold the two 33 percent interests for only $5,000 each. At the hearing, prompted by - .w ??rm Whitey?s unusual deals \Xi. I is i wee; 43,3." 4 J. is}? 23% We: plication to acquire the Street Deli in South Boston, he was asked by licensing board chair- woman Andrea Gargiulo how long he had known Bulger. ?I?ve known James Bulger since I was about 13," Weeks said. Eleven months after Weeks appeared before the licensing board where he had down- played his ties to Bulger Bulger hit the real estate num- ber at the Liquor Mart, courtesy of Weeks and O'Neil. Bulger bought out Weeks? and Flemmi's interest in the proper- ty for $40,000, and then, on the same day, flipped the property to O'Neil and Gordon McIntyre for a fat $400,000. Bulger walked away with a paper profit of $360,000 on a property the city assessor?s of- fice said was worth only $74,000. Six weeks after Bulger, Weeks and O?Neil completed their Li- quor Mart shell game at the re- gistry of deeds, federal, state and local authorities swept through South Boston and Quincy, searching businesses and homes linked to Bulger?s al- leged organization. The raids were part of a long- running probe into drug traffick- LWeeks' ultimately successful ap- A: .. wilt . a N. . :ets?x?eagkfatr r? was? fetus: Raven?s shat?:?s?fatw?m. .: M. am 335% 3w?- t; ?3'93 3' or I 2? 5 yummy, i I ?35} - Jam: 5: ?wins; ?9 1min .H. g? 3313)., a M. t? wand-3M .3 '?xy 12's. 7? mp?. new, His-.?9.13 . My NV 35* 1- If?mu; vgg?rg?. ,stu x, .. m<3?s?3~ 11m. are it(asv?xazt?fm =1 1 ti?images teams a . at?. his? I imiawtg3'13"? ?int. SR?rWe,? Wm?- 5m haiw??ifa?m??'rg?wv: a} 33sz @332rawhu?h? 4.91.: .To 0m+~wr ?rvmn. .. 6%.02 13 .4 . I I bun-".33 +23? ?419634 can 36.37% .47 ?1 .A.. +63? 993?, K. m. . augth .40. . uQ. 1' 3. 5 than" is, S?s 3. 2.1-Han-.10s." .. .- I Fig" xl fr. .. 313m awnLax. 39:4 . .Il IMWF +oFJ39+v W1: no man Em .3. Wr?ass ?lov?smiss ov??w?Qa?ldin; . 3 at): . iice'u yr )1 - a Dc'I'd I .: ?3.115%. - 1.16 U4 ?2 . . 1-: ?111! n. .0 . a5hwy; l' 343?, I I vii?: v-A . -. '25.?rrim 1. I 5.14 ?at? 4" 5::mytm 46g; $39.15 mm: IA. mj?jjgw?g 5? s. 1 ?9.179191. 10.1. . f- 5518--Ienew 'iba . t?a?-r?gwc u? I1 gt" . 336 337C Memorandum SAC, BOSTON (182B-BS-55853) From SSA Subject: WINTER HILL INFORMATION CONCERNING Attached to this memo sent to Assistant United States Attorney forwarded to the FBI for information. criminal activity on the part of nd their associates and additional information is bein? sought at this time relative to the associate, and the current gambling location on the corner of Locust Street oer is a copy fzi_a_letter_1nns?gned) and 1e letter Date 12/2/91 b6 b? =cts andl I and Dorchester Avenue in Dorchester. If cases should be opened re preliminary investigation determines that the criminal activity of b?C and their associates, separate sub files will be initiated. Until that time, a lead is being set forth under control file 182B-55853 for further evaluation. IEAD: BOSTON AT DORCHESTER, MASSACHUSETTS Will nhtain complete identity of Winter Hill associate Will ascertain activity at alleged gambling ar are coated at Locust and Dorchester Avenue in Dorchester, Massachusetts. '11 a to determine ownership b6 of the game relative to and Will ascertain b7c subscribers to telephone numbers 282-9485 and 961?1908 and 961- 5706. conduct additional investigation as determined by information contained in attached letter. 3 i?f;;buhd4;f?a. ?$1222; 5/2? 23c 43/ 1573 c: 55 5?36 7 b6 b?C /7 0:5 b9; 137C r/ 1 I Fo-asd (Rev. 5-8-81) . (Indicate page, name of newspaper, city and state.) BOSTON GLOBE (Mount Clipping in Space Below) BOSTON 1 MA Date: Edition: 1/7/92 MORNING i I Title: 1 OLD CRIME BOSS J. Characteris CHARGED ANEW or Classification: 1 Submitting Office: char ed anew ,ugandm M, ,By Andrew Blake Vb; horns turned up? nothing illegal, federal of?- GLOBE STAFF Clals said. Law enforcement of?cials say Winter, a con- Howard T. Winter, who once rivaled Ma?a chiefs for the title of most powerful organized crime leader in New England, was remanded to federal custody yesterday pending a bail hear- . ing Monday on charges of selling cocaine. Winter, 62, was arrested sunday about a A mile from his Millbury home south of Worcester I Howard T. Winter is accused of being what he has said he detests the most: a drug pusher. Page 15. it victed racketeer, once headed the Winter Hill i i Gang in Somerville, and identify him as an asso- ciate of former Patriarca family underboss Gen- naro Angiulo and reputed organized crime the company of his wifeLEllen. A search of ?gure Jam?s?(Wl?tey) Bulger. - Also arrested Sunday on cocaine distribu- tion charges was Gennaro L. Farina, 5'7, of Somerville, a longtime Winter associate, and his son Robert Farina, who was charged with i1- legal possession of a silencer. A third man, Ken- neth Schiavo of Medford, also is being sought in charges. 1j The silencer charges against Robert Farina were dropped yesterday in US District Court WINTER, Page 22 connection with the cocaine distribution I L, ?f?H IWINTER Continued from Page 1 for lack of evidence. Federal authorities said several semiautomatic Mac 10 ma- chine pistols and ri?es were seized at the Farina home. ?This is a very signi?cant mat- said US Attorney Wayne A. Budd, in a news conference after Winter and Gennaro Farina ap- peered before US Magistrate/Judge Lawrence P. Cohen. strongly suggest that more kilograms are involved and that will go to the?federal grand jury soon,? Budd said. He said some six addi- tional kilograms were thought to be involved with Winter and Gennaro Farina. A kilogram is about 2.2 pounds. 1 . Budd also hinted that the ulti- . mate investigation \may be of a much broader scope than the arrests Suna day indicate,? noting that an agent Of?ce of Labor'Racketeering also was involved in the 31/2-year ?on- going investigation.? now,? said Budd. Budd also declined to say if the arrests of Winter and Gennaro Fari- na indicated a resurgence of the remnants of the Winter Hill gang or if the alleged cocaine distribution According to federal af?davits, State Police from the Worcester dis- trict attorney?s office, along with fed- eral agents from several agencies, have been investigating Winter and others since June 1988. Detailing two drug transactions Although their arrests involve Ionly one count each of distributing lone kilogram of cocaine, on last Aug. f1 for Winter and Aug. 3 for Gennaro ?Farina, the affidavits of Drug En- jforcement Agency agent Daniel Do- fherty detail alleged cocaine sales in- volving Winter, Farina and a ?wired? informant between May and August. On Aug. 1, according to the .davit, the informant picked Winter. ;up at _his home and while driving to 'Boston discussed the purchase of two kilos of cocaine. They stopped for Winter to use a pay phone and then drove to the Caldor parking lot Western Avenue, in Brighton, shortly before 9 am. About 10 min- utes later, a man driving a gold ag- . .- England organized crime. Sentenced for race-mung scheme Winter, wearing a blue parka, jeans and jogging shoes, told Cohen he is unemployed and living on a dis- ability pension. He receives $166 a week in workers? compensation after an accident Feb. 5, 1986, when he was employed as a used car sales- man. If convicted of the cocaine distri- bution charges, Winter and Gennaro Farina face a minimum mandatory ?ve years in federal prison. They could receive up to 40 years along with a $2 million ?ne, Winter has spent six years in prison. A 1979 federal indictment charged him and 20 others with op- erating a multimillion-dollar scheme was linked to other members .- 5. to ?x races at six East Coast horse racing tracks. He was sentenced for the race-?xing and a separate con- viction in state court for extortion in- I from the US Labor Department?s volving pinball machines. He was re- leased in 1985. am not able to offer details uar entered the lot and met with Winter for about ?ve minutes. A meeting was set for noon, at the parking lot of the Golden Spoon Res- taurant in Hopkinton. At that time, according to the af- ?davit, the informant?s car pulled -into the lot and a short time later Winter?s car pulled up next to it. Winter went to a pay phone and a few minutes later ?surveillance agents observed Gennaro Farina ar-= shortly before 11 am. at the La Quinta Restaurant, later renamed Fanny?s Bastaurant, on Route 9 in Westboro./ ?Surfeillance agents observed .the CI hand Winter a plastic bag containing $27,000 in cash that gov? ernment agents had given to the CI earlier that morning,? according to Doherty?s af?davit. Winter?s lawyer, Albert Cullen, said outside the court that he had rive at the parking 10?; in his graX/neth?fg to say'about the charges. Lincoln Town Car,? parking near Winter?s and the informant?s cars. ?Farina opened the trunk, re- moved a brown paper bag and hand- ed it to Winter. Moments later Win- ter placed the bag in the rear of the CPS [con?dential informant?s] vehi- cle. Inside the bag was approximate- ly one kilogram of cocaine,? accord- ing to D_oherty?s af?davit. Lawyers decline to comment The alleged payoff came the next day. Winter and the informant met .James E. McCall, a lawyer repre- senting Farina, said, plea of not. guilty will be entered. That?s all I can say at this time.? Assistant US Attorney Paul Kelly said Schiavo?s lawyer had contacted his office to ar- range for Schiavo?s surrender. Doherty?s af?davit also detailedl an Aug. 3 meeting in which Gennaro Farina allegedly handed the infor- mant a shopping bag containing about a kilo of cocaine. Winter was allegedly paid $27,000 for that trans- action on Aug. 8. k- A Fla-350 (Rev. 5-8-81) (Mount Clipping in Space Below) *7 awirr_ai 7 y~fwt?w Winter? a, WW 3:01? of the #7 By Kevin Cullen GLOBE STAFF Fifteen years ago, Howie Winter was King of The Hill. Winter Hill. That was when everything went his way. That was when the Irish mob, em- bodied by the Winter Hill Gang, was in the big leagues, shaking down bookies from Southie to Lowell, loaning money to long-. shoremen, doing contract hits for the Ma?a. Polyester Was big, and the cars the Irish' gangsters drove were bigger. Today, if you walk down Marshall Street in Somerville, past the garage where' Howie used to hold court, you?re more like- ly to bump into some kid from El Salvador than some plug-ugly with an Irish surname. Like disco and the Big Bad Bruins, the Winter Hill Gang is but a relic of the wild and woolly 19705, something recalled with a mix of nostalgia and distaste. And nowhere' slide than the plight of Howard T. Winter. .he has said publicly he detests the most: a "1980 by an angel dust pusher who Sper- heap . (Indicate page, name of newspaper. city and state.) BOSTON GLOBE Date: BOSTON MA . Edition: 1/7/92 MORNING Title: WINTERS SLIDE FROM TOP OF HEAP Character: or Classification: Submitting Office: is its fall from grace better exempli?ed Yesterday, Howie Winter was lugged into US District Court in this, his winter of discontent, accused of being the very thing i Indexing: pusher. Winter is an unlikely cocaine traf?cker, ?l given his public pronouncements on the scourge of drugs and the fact that his best? ?'iend, Sal Sperlinga, was shot to death in linga and Winter had warned to stay out of . Somerville?s Magoun Square. Sperlinga had slapped the guy around. But law enforcement authorities say. that Winter?s metamorphosis from under? world kingpin to free-lance drug traf?cker I is common in this day of crumbling, criminal enterpriseanowie, they say, heard the call i BACKGROUND, Page 22 Howie Winter is brdught to court fer arraignment. 3 GLOBE STAFF ?Mag??$58737? .0 I BACKGROUND Continued ?~om Page 15 of the marketplace: if you can?t beat ?em, become one of ?em. For two decades, Bob Long po- liced and pursued Howie Winter and his minions. Now, two years after leaving the Massachusetts State Po- lice to join the private sector, Long remarked on the irony of how his and the careers of the Irish wiseguys he once chased have followed a simi- lar path. ?They all seem to go a certain route, this path that stretches from the late 1960s to the late 1980s,? said Long, an investigator for LGF Asso-_ ciates, a Braintree ?rm that special- izes in white-collar investigations. ?They start cut bookma?king, :loansharking, even robbing banks. 'Then they go into truck hijackings. Then it?s the more pro?table and less bulky: drugs. They start with marijuana, then move into cocaine. Most of them left that and went into real estate. ow that I?m doing nancial investigations, I see these names popping up, guys that I was chasing 15 years ago.? Winter emerged from gang wars The Winter Hill Gang was actual- 1y a hybrid of several predominantly Irish-American organized crime groups that were riddled by bullets and instability in the_ Boston gang, wars of the 1960s. More than 60 men were killed in those wars. After Buddy McLean, leader of the Somerville gang, fell victim to the Charlestown contingent led by. the McLaughlin brothers, McLean?s trusted lieutenant, Howie Winter, stepped up. Though not as much a peacemaker as a bene?ciary of the peace that followed, Winter brought to the Irish mob a sense of leader- ship and stability that had been lack- ing, authorities say. The Winter Hill Gang, operating out of a nondescript garage in the neighborhood from which it took its 7' A name, became a pro?table subcon- I tractor to the better organized and more established Ma?a. In return for the occasional hit, and a portion :of the proceeds, the Italians let their Irish brethern carve out their own niche in_the rackets. During a 1981 conversation that I was recorded 'by the FBI, Ilario MA. Zannino, the then No. 2 man in the Boston Ma?a, extolled the vir- tues of hiring reputed Winter Hill operatives James J. (Whitey) Bulger and Steve (The Ri?eman) Flemmi to do their dirtywork. ?These are nice people,? Zannino . lectured his underlings in a North I. End gambling den. ?These are the I kind of. . . people that straighten a thing out.? Winter became so identi?ed as the leader of the Irish mob that some began to believe the gang took its name from him. Next to Gennaro J. (Jerry) Angiulo, then underboss for the Patriarca crime family, Win- ter was considered the most power- ful gangster in Massachusetts. All that collapsed, however, with a 1979 federal indictment charging Winter and 20 others with operating a multi- million-dollar scheme to ?x races at six East Coast horse tracks. $166 in compensation For the race-?xing and a sepa- rate conviction in state court for ex? tortion involving pinball machines, Winter spent six years in custody, emerging from prison in 1985 to get a job that some said be?t his life ex- perience: used car salesman. It was while working at that $250-a-week job at the Millbury ga- A rage owned by William Gingras, his parole sponsor, that Winter said he hurt his back. By 1989, just a decade after a snap of his ?ngers could com- mand thousands in tribute, Howie 1 Winter was subsisting on $166 in weekly workers? compensation. That information was gleaned ?om records obtained through a Freedom of Information Act request on .0 reporter not to publish the article: which detailed how Gingras had made Winter the bene?ciary of a real estate trust that was building? duplex homes in Worcester. 5 moved out of Boston,? Winter! explained. ?I?ve tried to start a new: life. I?m trying to be a person whol faded into the background. I?ve done} nothing wrong. . .I?m trying to mind] my own' business and you peoplel won?t let me.? . Winter also explained how muchi he hated drugs, especially because of} what had happened to his pal and partner, Sperlinga. In the summer of 1988, state troopers assigned to the Middlesex County unit Long headed and troop- are from the Worcester County dis- trict attorney?s of?ce began an inves-i tigation into allegations that Winterl I and Richard Sperlinga, son of Win- ter?s late associate, were involved in ll cocaine traf?cking. That investigation came to an abrupt halt when Sperlinga recog-% nized a trooper who was tailing him i and Winter in a Worcester shopping plaza parking lot. Police searched Sperlinga, Winter and their cars, but found no evidence of wrongdoing. if?? Authorities, however, say the in- formation gathered eventually paid . off. Ricky Sperlinga, for whom Win? . 3 ter had become a father ?gure, was - convicted last May of selling the same drug, angel dust, that his fa- ther and Winter had railed against. And yesterday, Howie Winter stood in federal court, facing charges that could put him behind bars for . the rest of his life. . Bob Long said few of the old 3Irish gangsters have been able to go legit, as Winter said he tried to do. The only one who seems to have cre- ated a legitimate income to match . Howie Winter is seen waiting on a bench in Superior Court in this his lifestyle, in fact, is Winter?s old 1974 photo. lieutenant, Whitey Bulger, who won the Lottery last year. ?led by a Globe reporter in 1988 as on. It was during that period that ?Maybe,? Long?mused, ?Howie part of an investigation into Winter?s Winter and a Globe reporter had a should have just bought some more, activities since his release ??qm pris- discussion. Winter urged the lottery ticke em? \4 A FD-350 (Rev. 5-8-81) (Mount Clipping in Space Below) 4 I A Former crime boss to busted on cocaine rap By SHELLEY MURPHY Former Somerville gang leader Howard T. "Howie" Winter, who once ruled an organized crime faction whose power rivaled the Mafia, was charged yesterday From Page 1 soc:- ates. James J. "Whitey" Bulger and Stephen "The Rifleman" Flemmi, according to sources. Instead of a deal that would have brought him protection and a reduced prison term, a Winter chose to face drug charges that will put him in prison for the rest of his life if he?s convicted, sources said. Winter is accused of arrang- ing the delivery of six kilo- grams of cocaine to a friend who was secretly cooperating with a probe by the federal Drug Enforcement Administra- r? i with cocaine trafficking. The 62-year-old gang- ster refused to cooperate after his arrest when urged by investigators to 1 .turn informant on his for- mer Winter Hill gang as- ?Turn tofage 20 tion, the Massachusetts State Police and the U.S. Department of Labor's Office of Labor Racketeering. A man who identified him- self as Winter?s friend and ar- rived at the courthouse in a black, gold-trimmed Cadillac, claimed Winter was the target of a "set-up" by investigators who hoped to turn him against Bulger and Flemmi. The man, who asked to re- main anonymous. claimed Winter was whisked to a Fra- mingham hotel shortly after his arrest early Sunday morn- ing and offered a deal. "They want him to turn on two guys." said Winter's friend. ?They gave him a choice, wit- ness protection or a death sen- tence life in jail." When asked if Winter would cooperate against Flemmi and Buiger, the friend said, ?He won?t do it. Would you do it? Would you turn in your two best friends in the whole world?" Attorney Albert J. Cullen Jr., who represents Winter. said. can?t comment on any- thing." U.S. Attorney Wayne A. . Budd refused to comment on whether Winter had been of- fered a deal, but sources con- If firmed Winter had been asked to cooperate in the ongoing probe. Brushing aside Winter?s] friend's suggestion that Winter 1 was targeted to get to Bulger (Indicate page, name of newspaper, city and state.) Lam BOSTON HERALD BOSTON, MA. 1 1/7/92 MORNING I'Titie- FORMER CRIME BOSS I BUSTED 0N COCAINE RAP Character: or Classification: Submitting Office: Indexing: {and Flemmi, ,Agent-In-Charge Carlo Boccia .said, ?It was a classic drug in- fvestigation wherein (Winter) ibecame a suspect and is now a l? defendant." I Worcester County District Attorney John J. Conte said I State Police assigned to his of- fice launched the probe in June 1988 and turned to Budd's office I and the federal agencies for help when the case escalated. "This is very much so an on- going investigation. It involves other individuals," said Conte, hinting at more arrests-?We feel today that we?ve made sig- nificant inroads into whatever you want to call it Mob crime organized crime . drugs. You can call it whatever you want, but it?s there. It?s a very significant arrest of a very significant crime figure." Federal complaints filed in U.S. District Court in Boston charge Winter, of 14 Tiffany Circle, Millbury and Gennaro L. Farina, 47, of 100 Wheatland I St., Somervill'e, with distribut- ing more than 500 grams of co- caine. A third man, Kenneth Schiavo, 49, of Medford, was be- ing sought yesterday on simi- lar charges in a sealed'com- plaint. Raids by investigators led to the seizure of six automatic weapons at Farina?s home. Gun charges were initially brought against Farina-'5 son, 'Robert, because he lives in the same b. DEA Special ties, sources said. house, but were dropped almost immediately. Winter was secretly record- ed and observed delivering co- caine to the informant on four occasions in the Hopkington area between May and No- vember, according to an affida- vit by DEA Special Agent Dan- iel M. Doherty. Gennaro Farina accompan- ied Winter during two of the drug deliveries and made one delivery alone, the affidavit says. The informant paid approxi- mately $27,000 per kilogram for the drugs and carried a trans- mitting device to enable inves- tigators to follow him to the drop-off sites. The informant claims he bought cocaine from Winter and? his associates on another six occasions in 1990. U.S. Magistrate Judge Law- rence Cohen ordered Winter and Farina held without bail pending a detention "hearing Monday after Asstistant U.S. attorneys George Vien and Brien O'Connor argued they may pose a danger to the com- munity or flee if released. Appearing in jeans, a green- and-white striped shirt and a navy parka, Winter described himself as unemployed and liv- ing on a disability. He asked for a court-appointed lawyer. His wife, Ellen Brogna, 37, gasped when prosecutors an- nounced Winter faces five Ato~40 years in prison and a $2 million on April 3. 1981. fine, if convicted. Winter was described by Conte as someone who ha been leading a "low-key life, style" recently. I By comparison, Winter and his associates made daily head- lines in the 19603 during Bos- ton's bloody gang wars. Winter survived to become the leader1 of the Winter I-iill gang after his boss, Buddy McLean, was murdered by rival gangsters. A 1986 report by the Presi- dent?s Commission on Organ-' ized Crime claimed Winter?s; gang was involved in ?drug; trafficking, hijacking, loan-l sharking and contract 1nurder"? on behalf of a branch of the Ma-' fia run by then Boston Mob? boss Gennaro ?Jerry? Angiulo. The report claimed the} Winter Hill gang controlled cal 25 of the International: Brotherhood of Teamsters and; Boston's docks. But, law enforcement offiw cials said the Winter Hill gang? was in disarray after Winter faced back-to-back convictionsj in the late 19705 on state ex-1 tortion charges and a federal] race fixing rap. Since Winter's release from; prison seven years ago, he's? operated mostly in the Worces-i ter area, sources said. i Meanwhile, Bulger an Flemmi reportedly control- criminal activities in South Boston, the South End, Rox-1 bury, Quincy, Weymouth and other South Shore communi- While there may be dispute about Winter?s influence today, FBI tapes of conversations bugged at Angiulo's North End headquarters in 1981 reveal a close tie between the Mafia and Winter. ?Do you know that the Hill is us?" reputed mob consigliere Ilario Zannino told an associate Angiulo said he met Winter in Providence, R.I., with then i - reputed New England don Ray- mond L.S. Patriariaca, who died in July 1984. ?And I think Raymond gave (Winter) a vote of confidence,"? Angiulo said. Zannino agreed, (Pa~ triarca) liked him very much." )1 1? I J/n 3.5.55 .g ts}. . a pit/X vwf/u . ?axJava 3?1313.) if. ?as aw ?i ink 230:969: 1925 mco<9 a 92mFm. 0632 0823050 3 wo?o: