Win a Lifted 2019 Ford F-350 Lariat Ultimate, $10,000 Cash and Your Choice of Trailer

What you're looking at

Dirt Monkey's fifth giveaway — the "DM5 Midnight Trail Package" — is built around a 2019 Ford F-350 Lariat Ultimate crew cab, 4x4, in Blue Jeans Metallic, with roughly 123,800 miles showing. Under the hood is the 6.7-liter Power Stroke V8, rated at 450 hp and 935 lb-ft in this model year, sending it through the six-speed TorqShift automatic.

It hasn't been left alone. The truck sits on a 4-inch lift wearing 37-inch AMP tires on 24-inch Fittipaldi wheels, with 35 percent tint on the windshield and 5 percent on the sides and rear, plus paint-matched trim. Inside, the Ultimate package earns its name: heated and cooled seats, a twin-panel powered moonroof, and a powered sliding rear window.

The truck is only part of it. One winner takes the F-350, $10,000 in cash, and their choice of exactly one trailer — a 2023 Horizon tandem-axle gooseneck dump trailer, a 2015 Keystone Cougar X-Lite High Country 33RES travel trailer, or a 2026 FLOE CargoMax XRT 13-73T utility trailer. You pick one and the other two go away with no credit for the difference in value.

Why it matters

This is a prize aimed squarely at people who actually work out of a truck, and the trailer choice is the tell. The Horizon gooseneck dump is the highest-value option at a stated $20,000 and the most immediately monetizable if you run a crew; the Cougar is a 36-foot, three-slide travel trailer with a polar package and heated underbelly for someone who'd rather chase a campsite; the FLOE is the light, practical, bi-fold-ramp answer for hauling machines and toys.

The truck itself is a genuinely desirable spec. 2019 is the last year of this Super Duty configuration before Ford's 2020 refresh brought a 10-speed automatic and a different high-pressure fuel pump, so this is the end of a distinct era rather than a leftover.

Be clear-eyed about the build, though. Twenty-four-inch wheels wrapped in 37s look exactly like they sound, but the ride is firmer, replacement rubber is expensive, and the combination narrows the resale audience compared to a stock-height Lariat. The lift also changes the geometry on a truck that was engineered to tow heavy — worth understanding before you hitch that gooseneck to it.

The bigger caveat is mechanical. A 2019 6.7 runs the Bosch CP4.2 injection pump, and that pump's failure mode is the well-documented one: when it lets go it can send metal through the entire fuel system and turn a repair into a five-figure event. At 123,800 miles this engine is barely middle-aged, but the CP4 is the line item any honest buyer budgets around, alongside the usual turbo and emissions-hardware upkeep.

The fine print worth knowing

The sponsor is Dirt Monkey Shop LLC, a Minnesota company at 8362 Tamarack Village, Ste 119, Box 445, Woodbury, MN 55125 — the retail arm of Stanley "Dirt Monkey" Genadek's landscaping and equipment channel. Entries run on the storefront: the rules set one base entry per $1 spent on eligible products, and site multipliers scale it from there. Dedicated Quick Entry packs run $25 for 3,125 entries at 125x, $50 for 9,375 at 187.5x, and $100 for 25,000 at 250x, and a first order of $100 or more adds 1,000 bonus entries.

The free route is real and it is unusually generous. A handwritten 4x6 postcard earns 50 base entries multiplied by whatever eligible multiplier you claim, which means a postcard claiming the top advertised multiplier is worth the equivalent of a $50 purchase at the same rate. One postcard per envelope, no bulk mailings, and everything must be postmarked between July 23 and August 24, 2026 and received by August 31. Every entrant, paid or free, is capped at 100,000 entries total. Exact wording and the mailing address are in the free-entry section below.

Entries close August 23, 2026 at 11:59 PM CT, with the drawing on or after September 1. Florida and New York residents are excluded, along with U.S. territories and APO/FPO addresses; 18 and over only. The drawing is run by the sponsor rather than an outside administrator, which is common for creator-run giveaways — worth knowing, and worth weighing against the fact that Dirt Monkey names its winners publicly, with Cory Blanchard of Wichita, Kansas taking the DM4 F-350 and Duncan McKinney of La Crosse, Wisconsin taking the DM2 plow truck, and livestreams the notification calls.

Finally, the tax reality. The winner is responsible for all federal, state and local taxes plus title, registration, insurance, transport and delivery costs on a package the sponsor values between $62,613 and $75,000. The $10,000 cash component is the most useful thing in this prize package for exactly that reason — it is roughly the size of the bill you'll be handed in April.