US Magistrate Judge Marianne B. Bowler approved a search warrant in February allowing investigators to search an iPhone and a second cellphone seized from Desmond Crawford, who the FBI says is a member of the Columbia Point Dawgs and the likely triggerman in the shooting of a rival gang leader.

Apple Inc. is objecting to a request from federal prosecutors in Boston that it help unlock the iPhone of an alleged member of one of the city's most notorious gangs, according to court records — a case that echoes the government's high-profile fight with Apple in the San Bernardino terrorism case.


In an affidavit dated Feb. 1, FBI agent Matthew Knight wrote that he needed Apple's help to get into a passcode-locked iPhone 6 Plus that he suspected contains contact information for other gang members, associates, and drug customers. Knight also said messages on the phone probably detailed Crawford's gun- and drug-trafficking activities, plus plans for the drive-by shooting.

Based on wiretapped phone conversations, "I . . . know that Crawford used his [iPhone] to discuss details related to the shooting of a rival gang member," Knight wrote in his affidavit.

Apple declined to comment. But in a case involving a drug dealer in Brooklyn, Apple filed documents indicating that it has objected to a request to help unlock an iPhone in a case in US District Court in Massachusetts.

The San Bernardino, Calif., case triggered a raging national debate over privacy, security, and encryption. And the Boston case underlines a key fear of both Apple and privacy advocates: that if Apple cooperates in the San Bernardino investigation, it will be forced to do the same in thousands of more routine cases in which national security is not at stake, effectively creating for authorities a permanent "back door" into every iPhone in the United States.


"The government is asking Apple to hack our own users and undermine decades of security advancements that protect our customers — including tens of millions of American citizens — from sophisticated hackers and cybercriminals," Apple's chief executive, Tim Cook, wrote in an open letter to customers.

Crawford was arrested in November as part of a yearslong investigation by federal and local authorities into the Dawgs, dubbed "the largest, most violent and most feared organization in Boston" by US Attorney Carmen M. Ortiz.

Earlier in 2015, simultaneous raids resulted in gun and drug charges against 48 suspects tied to the group, which was founded in the Columbia Point housing development before its demolition in the late 1980s and then spread throughout the city and even to other states.

When Crawford was arrested, authorities said they also recovered a loaded handgun hidden in the gearbox of his rental car.

In California, Apple is waging a high-stakes fight against the US Justice Department's request that it help unlock the iPhone of Syed Rizwan Farook, who with his wife was killed by authorities after shooting 14 people at a San Bernardino County facility.

Both Crawford's and Farook's iPhones ran on iOS 9, an operating system that uses automatic encryption to hide the data on the phone from anyone who doesn't know its master PIN or passcode. A law enforcement official with knowledge of the Crawford case who was not authorized to speak publicly confirmed that Crawford's phone is the one referenced in the New York court records.


The affidavit filed by Knight seeks to compel Apple "to assist in the execution of the search warrant by bypassing the lock screen" of the iPhone, as well as to help extract and copy the data from his phone or provide his unlock code.

Harold H. Shaw, special agent in charge of the FBI's Boston office, declined to comment on the Massachusetts case. But in a statement, Shaw said that "it is extremely important for law enforcement to have access to digital evidence pursuant to a court order."

In California, the FBI wants Apple to create software that would let the government try thousands or millions of computer-generated passcode combinations to unlock Farook's iPhone. Without such software, an iPhone may temporarily freeze up or even delete all of its data when too many incorrect passcodes are entered.

The company maintains that the encryption technology embedded in the latest versions of its iPhone operating system prevents Apple from hacking into the phone.

In his letter to customers, Cook said the government is asking the company to create a back door that would leaves it its customers vulnerable to hackers.

"Once created, the technique could be used over and over again, on any number of devices," Cook wrote. "In the physical world, it would be the equivalent of a master key, capable of opening hundreds of millions of locks — from restaurants and banks to stores and homes. No reasonable person would find that acceptable."

Bruce Schneier, a security technologist at Harvard University's Berkman Center for Internet and Society and a critic of the government's request, said the Apple case raises a keen national question: "Do we want security or surveillance?"


"The danger is not whether the FBI submits one request or a thousand, it's forcing Apple to create the tool," Schneier said. "Once the tool exists, they'll use it a million times, and we'll all be vulnerable."

In the San Bernardino case, Apple is appealing a federal judge's order that it help crack the iPhone. Conversely, the judge in the Brooklyn case declined to order Apple to cooperate, which the Justice Department is appealing.

In Boston, the most recent record in Crawford's iPhone case is the search warrant that was issued Feb. 1.

Crawford's lawyer, Rudolph F. Miller, of Milton, said he had not heard that Crawford's phone was the subject of dispute between Apple and the Department of Justice, but said he would inquire about the matter with prosecutors. Crawford is currently in jail, awaiting trial on federal racketeering charges.

Dan Adams can be reached at dadams@globe.com. Follow him on Twitter @DanielAdams86. Milton J. Valencia can be reached at mvalencia@globe.com. Follow him on Twitter @miltonvalencia.