The Bulger Complex: Common Conception of Organized Crime Leads to an Impracticable Nexus Requirement in Massachusetts Wiretap Statute

By Jess Megee*

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Famous tales of groups implementing violent means to further their illegal business operations have shaped the common conception of organized crime in Massachusetts. In response to this type of crime, the Massachusetts legislature enacted Massachusetts General Law ch. 272, § 99 (Section 99), which authorized police to use wiretaps to investigate organized criminal activity.1 Section 99 substantially relies on this common conception of organized crime, only authorizing wiretaps where criminals have committed a “designated offense” in connection with “the organized criminal trade.”2 This standard, however, has become impracticable in the modern criminal landscape.

The issue with Section 99’s efficacy is a direct result of the type of criminal activity prevalent in Boston. Since the fall of La Cosa Nostra and Whitey Bulger’s Winter Hill Gang, an array of highly territorial “street gangs” have dominated Boston’s underworld.”3 Although these entities engage in many of the same criminal operations as their more famous predecessors, they do so with less clear and defined motives. The difficulty in deciphering a clear motive renders the standard for upholding single-person consent wiretaps far too exacting to investigate gang related criminal activity. In particular, Section 99 proves inadequate as a tool to investigate gang violence, which is commonly motivated by retaliation, longstanding feuds and stature in the community, rather than any pecuniary end.4

I. The Statute

In 1968 the Massachusetts legislature amended Section 99 to allow for electronic interception of communications in a very limited class of situations.5 One such situation involves the interception of communications of participants in organized crime.6 These wiretaps are permissible without a warrant provided that the recording occurs outside of a home, or can be supported by a “Blood Warrant” if they are to be recorded inside of a home.7

In its preamble, the statute defines organized crime as “a continuing conspiracy among highly organized and disciplined groups to engage in supplying illegal goods and services.”8 Additionally, the statute prescribes a list of “designated offenses” including murder, arson and narcotics trafficking.9 In order for a wiretap to comport with Section 99, investigators must have probable cause to believe that the target of the wiretap has committed a designated offence.10 Additionally, the Supreme Judicial Court has required in several decisions that an affidavit in support of a Section 99 warrant contain a sufficient connection between the alleged designated offense and “organized crime,” including a specific nexus to the “supply of illegal goods and services.”11 This nexus requirement has impeded the use of wiretaps in investigations of street gangs.12 Justice Gants of the Massachusetts Supreme Judicial Court noted this issue in his concurrence in Commonwealth v. Tavares:

By limiting electronic surveillance to designated offenses "in connection with organized crime," § 99 prohibits electronic surveillance from being used to investigate designated offenses, including murder, that are committed by disorganized criminal gangs or even by organized street gangs that do not engage in supplying illegal goods and services, such as narcotics.13

The legislature has also taken notice of this issue and has proposed changes to Section 99, including removing the “in connection with organized crime” language from the designated offenses section.14 While amendments to Section 99 would certainly allow law enforcement greater latitude in using electronic surveillance, alternatively courts could modify their interpretation of its requirements to better apply to today’s street gangs.

II. Street Gangs

In 2006, Boston had 65 active street gangs with an estimated total membership of 1,422 youth.15 Unlike gangs in other major American cities, such as Los Angeles and Chicago, Boston Gangs tend to be smaller, averaging about twenty-two members, and generally do not have national or even regional affiliations.16 As such, Boston gangs are less organized than many traditional gangs and occupy smaller territories.17

Despite their small size and lack of organization, Boston gangs are responsible for a disproportionate amount of the violence in the city.18 In fact, between 2000 and 2006, Boston’s youth violence homicide rate jumped 160%, largely as a result of gang-related activity.19 With eight gang-related homicides in January 2014 alone, gang violence in Boston has been brought to the forefront of public attention.20

III. Nexus Issue

The famous tales of Massachusetts’ organized crime figures, narcotics, extortion and gambling activities have certainly influenced the common conception of “organized crime.” The violence precipitated by these infamous underworld figures, much of which was plainly done in furtherance of pecuniary ends has drawn particular attention. For example, during the recent trial of Winter Hill Gang leader James Whitey Bulger, much of the testimony focused on murders largely motivated by the gang’s fervor to avoid prosecution for its illegal business operations.21 This clear connection between illegal business operations and violent acts is not as apparent in modern gang activity.22

One example of the inapplicability of this standard can be found in Commonwealth v. Tavares, where the Supreme Judicial Court upheld an order suppressing conversations recorded subject to a Blood Warrant.23 The Court based its decision on the fact that the warrant’s supporting affidavit failed to allege that the designated offense, a homicide committed by a gang member, was done in furtherance of “organized crime.”24 The affidavit contained information including the Tavares gang’s propensity for carrying firearms and its members’ past violent offenses and that gang members worked together to avoid capture.25 However, the Court deemed this information insufficient to show the requisite level of organization.26 Additionally, the Court noted that another dispositive factor in its determination was that there was no evidence that the murder was committed in furtherance of the “organized criminal trade” (i.e. the supply of illegal goods and services).27 Based on this requirement, it is abundantly clear that Section 99’s efficacy in the gang context, is limited to crimes in which a reasonably clear line can be drawn between the violent act and the sale of illegal goods such as narcotics or firearms.

IV. Solution

A simple solution to this problem would be for the judiciary to constrain the nexus requirement to the first part of the preamble’s definition of organized crime. As such, the Commonwealth would still be required to have probable cause to believe that the target of the wiretap committed a designated offense. Next, the Commonwealth would need to demonstrate reasonable suspicion to believe that the target committed the offense as a member of a “continuing conspiracy among highly organized and disciplined groups.”28 Lastly, the Commonwealth would have to provide reasonable articulable suspicion to believe that the ongoing criminal conspiracy, of which the target was a member, was connected to the provision of illegal goods or services. This augmented standard seems semantic, but its effect could be drastic. Indeed, placing the emphasis on whether an organized criminal entity committed the designated offense will allow Section 99 to provide a more robust investigative mechanism, while still serving to protect citizens from overzealous police actions.

Moreover, this article’s suggested standard is in accordance with the legislative intent of Section 99. In passing this section, the legislature noted the difficulties inherent in investigating organized criminal entities, including that organized crime “carries on its activities through layers of insulation and behind a wall of secrecy.”29 The legislature also noted that “organized crime [as it exists in the Commonwealth] is infiltrating legitimate business activities and depriving honest businessmen of the right to make a living.”30 As such, the legislature’s emphasis in passing the law seems to be rooted in the deleterious effect which the presence of organized criminal enterprises has on the community at-large and the difficult nature of investigating those enterprises.

With the legislature’s intent in mind, there can be little doubt that gang violence has had a significant negative impact on many communities in Boston. These negative impacts include lack of investment in the community, low community morale, and loss of life.31 The FBI has stated that gang activity in Boston has “used violence and intimidation to hold communities hostage.”32 Furthermore, there can be little doubt that investigations of violent street gang activity share many of the same difficulties as investigations into traditional organized crime, because organized street gangs share many of the same characteristics as classic organized criminal entities.33

An example of the type of crime that could be more efficiently investigated under Section 99, given this article’s amended standard, can be found in a recent case argued before the Supreme Judicial Court. In Commonwealth v. Hearnes,34 the Supreme Judicial Court upheld the denial of a defendant’s motion to suppress wiretap evidence.

The affidavit supporting the wiretap outlined the facts underlying a murder in the Roxbury area of Boston.35 According to the affidavit, the defendant was a member of H-Block, a known street gang in Roxbury with a propensity for obtaining and using firearms to increase its stature in the community.36 The affidavit further alleged that the defendant had committed the murder in housing project occupied by a rival gang, with the aid of other H-Block members, and at the direction of senior H-Block members.37 Additionally, during a hearing on the motion to suppress, a detective testified that, in his experience, most Boston street gangs deal in firearms and narcotics and specifically referenced the Board of Probation records of several H-Block members, which included entries for narcotics distribution.38

Applying this article’s suggested analysis to the facts in Hearnes, it is apparent that the wiretap in question would fall within the ambit of permissible recordings in Section 99. Indeed, the affidavit alleged sufficient facts to show the requisite level of organization, including a defined hierarchical structure within the gang and that members would often go on gang sanctioned “missions” to further the gang’s stature in the community.39 Furthermore, the detective’s assertion that H-Block distributed narcotics, corroborated by the references to narcotics offenses of known H-Block members, would suffice to show that the detective had reasonable suspicion to believe that H-Block was involved in the sale of illegal goods or services.40

The Court’s recent decision in Hearnes is grounded in the low bar the reasonable suspicion standard imposes.41 However, this article’s suggested bifurcated nexus requirement would avail law enforcement with a more powerful tool to investigate gang related violence. Augmenting the nexus to the supply or sale of illegal goods standard, will allow law enforcement agents to more easily obtain surreptitious recordings of gangs in the early stages of an investigation without delving into the motivation for the violent act.

V. Conclusion

While the foregoing analysis is intended to serve as a commentary on the current state of the law of single-person consent wiretaps, the legal landscape is likely to change soon. With cases pending before the Supreme Judicial Court and the legislature considering amendments to the statute, Section 99’s effectiveness in investigating and eventually prosecuting street gangs might well be realized. However, the interpretation of Section 99 detailed above would comport with the intent of the legislature and immediately permit more efficient investigations of street gangs.

* Candidate for Juris Doctor, Northeastern University School of Law, Class of 2014.

1 Mass. Gen. Laws ch. 272, § 99(A) (2014).

2 Commonwealth v. Tavares, 945 NE.2d. 329, 339 (Mass. 2011).

3 See generally Cannatta, Note: Achieving Peace in the Streets: How Legislative Efforts Fail in Combating Gang Violence in Comparison to Successful Local Community-Based Initiatives, 35 New Eng. J. on Crim. & Civ. Confinement 243, 244 (2009)(noting that “crime and gang violence are accepted and ingrained as a common standard in Boston’s troubled communities”).

4 See Braga et al., Symposium: Legitimacy and Criminal Justice: Losing Faith? Police, Black Churches, and the Resurgence of Youth Violence in Boston, 6 Ohio St. J. Crim. L. 141, 155 (2008) (noting that gang-involved individuals are often “caught up in ongoing cycles of retaliatory street violence").

5 Mass. Gen. Laws ch. 738, § 1 (1968) (current version at Mass. Gen. Laws ch. 272 § 99 (2010)).

6 Mass. Gen. Laws ch. 272, § 99(A).

7 See Mass. Gen. Laws ch. 272, § 99 (2014); Commonwealth v. Blood, 507 N.E.2.d 1029, 1034 (Mass. 1987) (holding that a warrant is required for surreptitiously recorded conversations in private homes).

8 Mass. Gen. Laws ch. 272, § 99(A).

9 Id. at § 99(b)(7).

10 Commonwealth v. Tavares, 945 N.E.2d at 339.

11 Id.

12 Id. at 340.

13 Id.

14 S.B. 771, 188th Leg. (Mass. 2014).

15 Braga et al., supra note 4 at 154.

16 Id.

17 Id.

18 Id.

19 Id. at 148-49.

20 See Adrian Walker, Sharp Turn in Mayor Walsh’s Day, Bos. Globe, Jan. 29, 2014, (discussing nine homicides occurring in January of 2014).

21 See generally Associated Press, Whitey' Bulger Murders: A Look At The 19 Murder Victims In Former Mob Boss' Trial, Huffington Post, Aug. 12, 2013, murdersn3744746.html (discussing murders allegedly committed by Whitey Bulger).

22 See, e.g., Commonwealth v. Tavares, 945 N.E.2d at 340 (discussing difficulties in using § 99 to investigate street gangs).

23 Id. at 330-31.

24 Id. at 339.

25 Tavares, 945 N.E.2d at 331-33.

26 Id. at 132-33, 138-39.

27 Id. at 339.

28 Mass. Gen. Laws ch. 272, § 99(A).

29 Id.

30 Id.

31 See generally 68 Blocks: Life, Death and Hope in Boston’s Most Troubled Neighborhood, Bos. Globe (May 7, 2012) (a five part multimedia series on how street violence has effected the Bowdoin-Geneva area of Dorchester).

32 Press Release, FBI Boston, Thirty Boston Gang Members Charged with Drug and Firearms Offenses (Jan. 17, 2013) available at

33 See Tim Delaney, American Street Gangs, 18-19 (Pearson Education, 2006) (noting the similarities between the classic conception of “organized crime” and organized street gangs).

34 2014 Mass. LEXIS 206 (Mass. Apr. 8, 2014).

35 Id. at * 8.

36 Id.

37 Id. at * 7-8.

38 Commonwealth v. Hearnes, 2014 Mass. Lexis 206, at * 10 (discussing the references to the defendant’s board of probation record during the motion hearing); id. at * 16 (discussing the detective’s experience with gangs selling firearms and narcotics).

39 Id. at * 5-9.

40 Id.

41 Id. at * 18 (finding that that the murder was committed was part of an “ongoing "feud" (or war) between turf-conscious criminal organizations involved in the sale of illegal drugs in adjoining territory.”).