Anchorage contractor gets $7.5 million Border Patrol order for transportation and guard services

An Anchorage company that has provided ground transportation for federal immigration agencies in Texas for more than a decade has a new $7.5 million order from U.S. Customs and Border Protection.

The order to Trailboss Enterprises, signed Sept. 25, covers ground transportation and facility guard services for the U.S. Border Patrol from Sept. 30 through April 30, 2027, according to the federal award record. The agency set the order aside for small businesses and received three offers.

The record lists Trailboss' Anchorage office as the place of performance and doesn't say where the service will be provided. Trailboss' other Border Patrol orders over the past year also listed Anchorage, but their descriptions are for ground transportation in Texas and New Mexico. The most recent of those, worth about $22.2 million, ran through Sept. 24.

Federal records describe what the work involves. A 2024 Border Patrol order based in McAllen, Texas, worth about $65.2 million, says its purpose was to provide ground transportation so agents and officers could focus on more traditional law enforcement duties. Under it, the company provided migrant transportation and guarded facilities. A 2023 order in McAllen, worth about $46.2 million, was for "transportation for non-US citizens." A 2025 order for transportation and guard services in Del Rio, Texas, was worth about $11.1 million.

Before its Border Patrol work, Trailboss held a transportation contract with U.S. Immigration and Customs Enforcement's San Antonio field office starting in 2012. The largest single order under that contract, covering 2014 to 2018, was worth about $107.7 million. The company also provided guard and escort services for ICE's Homeland Security Investigations office in San Antonio.

Altogether, Trailboss has received about $450 million in transportation and guard orders from the two agencies since 2012, according to federal spending records.

The company's federal work goes back further. Records show Trailboss holding military contracts since the early 2000s, maintaining aircraft ground equipment, handling visiting aircraft and running vehicle operations at Air Force bases in Alaska and around the country. In the 2000s it also supplied aircraft mechanics to Customs and Border Protection in Alaska.

Because Trailboss' recent Border Patrol orders list Anchorage as both the company's home and the place of performance, federal spending data counts them as money coming to Alaska, including the orders for work in Texas and New Mexico.