Federal Contractor Profile
Trailboss Enterprises, INC.
Federal contracting record: $414M obligated across 59 awards from 3 agencies, FY 2016–2026.
$414M
Total Obligated
59
Award Records
3
Agencies Served
7
NAICS Codes
Company Profile
Parent UEI (Unique Entity Identifier)
CKH8AS2PDEW3
CAGE Code
053B2
Address
201 E 3RD AVE, ANCHORAGE, AK, 995012503
First Federal Award
Oct 1, 2015
Most Recent Award
Aug 19, 2026
Federal Sales Analytics
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Hover any bar for YoY change + award count. Current fiscal year shown at reduced opacity (partial year).
Top Federal Agencies
- Department of Homeland Security$357M
86.1% of total obligations
- Department of Defense$57M
13.9% of total obligations
- General Services Administration$0
0.0% of total obligations
Top NAICS Activity
- $278M
- $113M
- $9.9M
- $8.4M
- $3.9M
- $1.1M
- -$378K
Recent Federal Awards
| Date | Agency | NAICS | Description | Amount |
|---|---|---|---|---|
| Jul 10, 2026 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | GROUND TRANSPORTATION TX/NM | $17M → |
| Jun 10, 2026 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | GROUND TRANSPORTATION TX/NM | $4.4M → |
| Jun 1, 2026 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | GROUND TRANSPORTATION TX/NM | $7.3M → |
| May 13, 2026 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | GROUND TRANSPORTATION TX/NM | $863K → |
| Jan 23, 2026 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | GROUND TRANSPORTATION TX/NM | $4.0M → |
| Jan 21, 2026 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | GROUND TRANSPORTATION TX/NM | $4.2M → |
| Jan 9, 2026 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | GROUND TRANSPORTATION TX/NM | $4.3M → |
| Nov 25, 2025 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | TX NM GROUND TRANSPORTATION | $100K → |
| Nov 25, 2025 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | TX NM GROUND TRANSPORTATION | $4.0M → |
| Sep 25, 2025 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | GROUND TRANSPORTATION TX AND NM | $4.3M → |
| Jul 28, 2025 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | GROUND TRANSPORTATION AND GUARD SERVICES | $3.7M → |
| Jul 28, 2025 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | GROUND TRANSPORTATION TX/NM | $3.4M → |
| Jul 8, 2025 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | GROUND TRANSPORTATION AND GUARD SERVICES | $4.0M → |
| May 27, 2025 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | GROUND TRANSPORTATION AND GUARD SERVICES | $3.9M → |
| May 1, 2025 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | GROUND TRANSPORTATION AND GUARD SERVICES | $4.3M → |
| Apr 16, 2025 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | THE PURPOSE OF THIS ORDER IS TO PROVIDE GROUND TRANSPORTATION SERVICE TO REDIRECT AGENTS AND OFFICERS TOWARD MORE TRADITIONAL LAW ENFORCEMENT DUTIES. THE CONTRACTOR WILL PROVIDE MIGRANT TRANSPORT AND FACILITY GUARD SERVICE. | $5.6M → |
| Feb 24, 2025 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | THE PURPOSE OF THIS ORDER IS TO PROVIDE GROUND TRANSPORTATION SERVICE TO REDIRECT AGENTS AND OFFICERS TOWARD MORE TRADITIONAL LAW ENFORCEMENT DUTIES. THE CONTRACTOR WILL PROVIDE MIGRANT TRANSPORT AND FACILITY GUARD SERVICE. | $7.8M → |
| Jan 16, 2025 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | THE PURPOSE OF THIS ORDER IS TO PROVIDE GROUND TRANSPORTATION SERVICE TO REDIRECT AGENTS AND OFFICERS TOWARD MORE TRADITIONAL LAW ENFORCEMENT DUTIES. THE CONTRACTOR WILL PROVIDE MIGRANT TRANSPORT AND FACILITY GUARD SERVICE. | $5.6M → |
| Dec 3, 2024 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | THE PURPOSE OF THIS ORDER IS TO PROVIDE GROUND TRANSPORTATION SERVICE TO REDIRECT AGENTS AND OFFICERS TOWARD MORE TRADITIONAL LAW ENFORCEMENT DUTIES. THE CONTRACTOR WILL PROVIDE MIGRANT TRANSPORT AND FACILITY GUARD SERVICE. | $450K → |
| Nov 15, 2024 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | THE PURPOSE OF THIS ORDER IS TO PROVIDE GROUND TRANSPORTATION SERVICE TO REDIRECT AGENTS AND OFFICERS TOWARD MORE TRADITIONAL LAW ENFORCEMENT DUTIES. THE CONTRACTOR WILL PROVIDE MIGRANT TRANSPORT AND FACILITY GUARD SERVICE. | $5.6M → |
| Oct 18, 2024 | Department of DefenseFA5570 501 CSW RCO | 488119 | OPERATION, INSPECTION, AND MAINTENANCE OF AEROSPACE GROUND EQUIPMENT, OPERATION AND MAINTENANCE OF FUEL FACILITIES, FUELS ACCOUNTABILITY, TRANSIENT ALERT SERVICES, AND SUPPORT FOR THE ROYAL INTERNATIONAL AIR TATTOO AT RAF FARFORD AND RAF WELFORD, UK | $647K → |
| Sep 30, 2024 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | THE PURPOSE OF THIS ORDER IS TO PROVIDE GROUND TRANSPORTATION SERVICE TO REDIRECT AGENTS AND OFFICERS TOWARD MORE TRADITIONAL LAW ENFORCEMENT DUTIES. THE CONTRACTOR WILL PROVIDE MIGRANT TRANSPORT AND FACILITY GUARD SERVICE. | $1.2M → |
| Sep 25, 2024 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | THE PURPOSE OF THIS ORDER IS TO PROVIDE GROUND TRANSPORTATION SERVICE TO REDIRECT AGENTS AND OFFICERS TOWARD MORE TRADITIONAL LAW ENFORCEMENT DUTIES. THE CONTRACTOR WILL PROVIDE MIGRANT TRANSPORT AND FACILITY GUARD SERVICE. | $4K → |
| Sep 20, 2024 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | THE PURPOSE OF THIS ORDER IS TO PROVIDE GROUND TRANSPORTATION SERVICE TO REDIRECT AGENTS AND OFFICERS TOWARD MORE TRADITIONAL LAW ENFORCEMENT DUTIES. THE CONTRACTOR WILL PROVIDE MIGRANT TRANSPORT AND FACILITY GUARD SERVICE. | $5.9M → |
| Sep 6, 2024 | Department of Homeland SecurityBORDER ENFORCEMENT CONTRACTING DIVISION | 561612 | THE PURPOSE OF THIS ORDER IS TO PROVIDE GROUND TRANSPORTATION SERVICE TO REDIRECT AGENTS AND OFFICERS TOWARD MORE TRADITIONAL LAW ENFORCEMENT DUTIES. THE CONTRACTOR WILL PROVIDE MIGRANT TRANSPORT AND FACILITY GUARD SERVICE. | $9.0M → |
Top Compensated Officers
From FFATA executive compensation disclosures. Reported when federal contract activity exceeds the statutory threshold.
- $209K
JOSEPH TOLLIVER, JR.
Rank 1 · Reported Jan 25, 2025
- $200K
MARVIN TOLLIVER
Rank 2 · Reported Apr 15, 2026
- $191K
ROBERT CHRISTE
Rank 3 · Reported Apr 15, 2026
- $170K
JOSEPH TOLLIVER JR
Rank 4 · Reported Aug 3, 2018
- $170K
JOSEPH TOLLIVER
Rank 5 · Reported Oct 19, 2023
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