U.S. v. Siciliano

• Decision Date: 26 August 2009
• Docket Number: No. 08-1745.,08-1745.
• Citation: 578 F.3d 61
• Parties: UNITED STATES of America, Appellant, v. Michael A. SICILIANO, Defendant, Appellee.
• Court: U.S. Court of Appeals — First Circuit

578 F.3d 61

UNITED STATES of America, Appellant, v. Michael A. SICILIANO, Defendant, Appellee.

No. 08-1745.

United States Court of Appeals, First Circuit.

Heard February 4, 2009.

Decided August 26, 2009.

Randall E. Kromm, Assistant United States Attorney, with whom Michael J. Sullivan, United States Attorney, was on brief, for appellant.

Robert M. Strasnick, with whom Andrews & Updegraph, P.C. was on brief, for appellee.

Before BOUDIN, STAHL, and LIPEZ, Circuit Judges.

LIPEZ, Circuit Judge.

After obtaining evidence that Michael Siciliano ("Siciliano") had ordered chemicals used in the manufacture of Methylenedioxymethamphetamine ("MDMA"), a controlled substance, agents from the Drug Enforcement Agency ("DEA") began an investigation. While interviewing Siciliano in his residence with his consent, a DEA agent, along with other law enforcement officers, conducted a protective sweep of the apartment. During the sweep, officers observed materials used in the manufacture of MDMA and a plastic bag containing an unidentified powder. On the basis of an affidavit containing this information, agents obtained a search warrant and searched the premises. Siciliano moved to suppress the evidence discovered in the search, arguing, inter alia, that the protective sweep was unlawful and that the agents would not have sought a warrant if they had not discovered what they believed to be contraband during the sweep. The district court granted the motion to suppress, and then denied the government's motion for reconsideration on the basis of newly discovered evidence.

On appeal, the government argues that the district court clearly erred in finding that the agents would not have sought the search warrant if they had not made the protective sweep, and that the court abused its discretion in refusing to grant the motion for reconsideration. After reviewing the record, we affirm.

I.

"We recite the facts as found by the district court, consistent with record support." United States v. Vilches-Navarrete, 523 F.3d 1, 5 n. 3 (1st Cir.2008).

A. The Investigation

In 2006, the Royal Canadian Mounted Police ("RCMP") informed the DEA that, in February 2005, Siciliano had purchased chemicals for use in manufacturing MDMA. The chemicals were delivered to 85 Surrey Street # 1, in Brighton, Massachusetts. Sometime thereafter, the DEA issued an administrative subpoena to eBay Inc. ("eBay"), seeking the transaction history on an account registered to Siciliano at the Surrey Street address. eBay provided the DEA with a transaction log on the account for June 2002 to August 2006. The log included purchases of chemicals, glassware, and other equipment, all delivered to 85 Surrey Street # 1. According to testimony from DEA Special Agent Anthony Roberto ("Agent Roberto"), the materials ordered are used in the manufacture of MDMA.

Agent Roberto testified at the suppression hearing that the information from RCMP and eBay was the basis for his investigation of Siciliano. After receiving the information from RCMP and eBay, he said, he decided to "obtain other evidence that there was manufacturing going on." In October 2006, Agent Roberto established surveillance at 85 Surrey Street # 1, and followed Siciliano from the apartment to nearby Northeastern University ("Northeastern"). Also in October, Agent Roberto looked through Siciliano's trash, and discovered financial statements bearing his name and the 85 Surrey Street # 1 address. According to Agent Roberto's testimony, the discovery didn't "ha[ve] any bearing" on the purchase of chemicals, and he did not apply for a warrant as a result of what was found. At that time, he testified, he did not know whether there was an MDMA lab on the premises or not, and he had never observed anyone come to the apartment to purchase drugs.¹

On November 16, 2006, Agent Roberto, accompanied by DEA Special Agent David DiTulio ("Agent DiTulio"), went to the apartment at 85 Surrey Street # 1.² Both agents wore plain clothes but were displaying their DEA badges. When the agents knocked on the door, Siciliano answered. The agents identified themselves and asked if he was Michael Siciliano. Siciliano initially denied his identity, but then admitted it after the agents produced a copy of his driver's license photo. Agent Roberto told Siciliano that they wanted to ask him some questions, and Siciliano invited them in.

The agents entered the apartment and followed Siciliano down a hallway leading to the rear of the residence. Halfway down the hallway, Agent DiTulio turned around and headed back out the door onto the porch, where he motioned to four law enforcement officers who had been waiting in their cars on the street. Agent DiTulio told the officers that Siciliano had agreed to speak with "us" and that they could come in. The officers entered the apartment and, along with Agent DiTulio, conducted a protective sweep of the premises. Three officers started in the front of the apartment, while two went to the rear. In the front, Agent DiTulio and Boston Police Detective Kevin M. Guy ("Detective Guy") opened the first doorway on the left, which led to Siciliano's bedroom. In the bedroom, Agent DiTulio found a dresser. The bottom drawer of the dresser was open, and in it Agent DiTulio observed an empty package of gelatin capsules. Elsewhere, in the "office," DEA Group Supervisor Jonathan Scheffler observed a plastic bag containing powder. The powder was not field-tested. Officers in the rear of the apartment discovered one of Siciliano's roommates in a bedroom adjacent to the kitchen.

Meanwhile, Agent Roberto continued to follow Siciliano down the hallway, which led to the kitchen at the rear of the apartment. As they walked, Agent Roberto asked Siciliano if there was anyone else in the apartment. Siciliano replied first that there was not, and then said that he was not sure and did not know. In the kitchen, Agent Roberto told Siciliano that he wanted to talk about orders of chemicals. Siciliano claimed that he had not ordered any chemicals. Agent Roberto said that he had, and Siciliano disagreed, whereupon Agent Roberto said that he had a list of Siciliano's purchases. Siciliano said that the orders had taken place six years ago, but when Agent Roberto disagreed, he said they occurred four years ago. At this point, the other officers in the apartment had completed their protective sweep and joined Agent Roberto in the kitchen.

Agent Roberto told Siciliano that the chemical orders had occurred that year. Siciliano said that the purchases had been for "Frank," a person he knew from Northeastern. Agent Roberto asked for Frank's last name, address, and phone number, but Siciliano could not or would not provide the information. By this point, Siciliano had become hostile; he was yelling, and, at one point, he pushed Agent Roberto. When one of the officers asked Siciliano if they could search the apartment, Siciliano said no. The officers, along with Siciliano, then left the apartment. Siciliano told the officers that he wanted to call his mother and an attorney. During Siciliano's phone call, Agent Roberto overheard Siciliano say that he "did something stupid" and "ordered chemicals."

Agent Roberto and Agent DiTulio testified that they then decided to "freeze" the apartment.³ Agent Roberto testified that what led him to freeze the apartment was "[p]art of the interview and part what was observed during the protective sweep." Agent DiTulio testified that "a series of factors led to us freezing the apartment. ... [T]here were conflicting statements, along with what we saw during the protective sweep." While two officers kept the apartment "frozen," Agent Roberto, Agent DiTulio, and the other officers left to seek a warrant.

Detective Guy prepared the affidavit supporting the warrant application. The affidavit set forth the information obtained from RCMP and eBay, Siciliano's evasive responses to questioning from the officers, his agitated demeanor, the gel capsules and powder observed during the protective sweep, and the overheard contents of the phone call. The warrant was issued and the search executed the same day. In Siciliano's bedroom, officers discovered 1.3 grams of 82 percent pure MDMA, a digital scale, plastic baggies, a plastic spatula, and the gel capsules observed earlier. In the apartment office, the officers discovered documents containing pictures and text describing how to make MDMA. Next to the documents were two computers and a hard drive, which the officers seized. The officers also located a basement in the apartment, where they discovered glassware and chemicals consistent with the manufacture of MDMA. Siciliano was arrested on state charges of possession with intent to distribute controlled substances.

In March 2007, several months after the search of the apartment, DEA computer forensic examiner Jill Mossman began a search of the seized computers pursuant to a second warrant issued specifically for that purpose. During the course of this search, she discovered what she believed to be files containing child pornography. After additional investigation not material here, a third warrant was obtained to search the computers for child pornography.

B. District Court Proceedings

In May 2007, Siciliano was indicted by a federal grand jury, and the state charges were dismissed. The federal indictment charged Siciliano with, among other things, possessing child pornography and attempting to manufacture MDMA. On August 15, 2007, Siciliano filed a motion to suppress the evidence obtained in the November 16, 2006 search of his apartment and the subsequent search of his computers. The government opposed the motion, and hearings were held on February 14 and 15, 2008.

On March 14, 2008, the district court issued an order granting the motion to suppress. The court held that Siciliano had not given consent for the four officers waiting on the street to enter his apartment, and that the protective sweep...