Timber Roots - Jay Oster Trucking

By Jason Todhunter

Jay Oster Trucking Inc started at a farm near Terry Montana where Jay Oster was born.  The family farm expanded to leasing a cattle ranch near Broadus for a bit then back to the farm in Terry. 

Jay was a freshman in high school when his parents divorced, and he ended up in Lewistown, MT.  When he turned 16, he told his mom that school was not for him and he was quitting.  She said “you are 16 so that is up to you but you are going to work, not sit around!”  He went to the local sawmill and immediately had a job.  After being in the mill for about eight months they were running out of logs and things were getting slow when a logger came in looking for some help and Jay’s logging journey was underway.

His first logging job was bucking logs on the landing.  After several weeks on the job Jay ended up in the hospital with a very severe cut to his leg; “rookie mistake; just really green!” said Jay.  With major damage to his Achilles tendon this injury took a year to heal.  Once healed, Jay went back to work bucking and operating a 380 B Timberjack cable skidder. Jay stayed with this contractor until 1994 when he went to another contractor who was logging pine sawlogs and pulp in the Roundup area.  “This outfit worked 14hrs a day and would have 4 trucks headed to the job when you were falling the first tree!”  The next job was in Big Sandy and was a tough and steep job.  Jay would skid with a grapple skidder and then help buck on the landing when he was caught up. That same year Jay and his girlfriend Rohnda had their first son David.   

A snowmobile trip to the Snowy Mountains in 1997 would change his career path again when Jay saw someone logging up on Alaska bench.  He was laid off at the time and even though there was some gravel/dirt to cross, rode his snowmobile up onto Osler Logging’s job where he met Brad Osler.  His trip was well timed as the loader operator was quitting that Friday.  Brad asked “can you load 6 loads a day?”  Jay said “I think so, I will sure try!”   This would start a 23yr career and friendship that continues today.  By the end of the week, it was 14 loads a day…Brad must not have wanted to scare him off! 

“Working with good people you learn a lot” says Jay and “I learned a lot from Brad and Jeremy Osler; they just do things right!”  Jay worked for Osler’s continued and in 2010 he bought his first truck from them and started his own business Jay Oster Trucking Inc.  This 1996 t800 was a great truck with the 60 series Detroit; burning 15 gallons of fuel less every day than other trucks; this number adds up over the course of a year!  He continued working for them both as a sub and employee where he would load trucks with their loader and then run his own truck as well. 

 In 2014 when the ‘96 hit 1.6 million miles Jay decided to upgrade.  He bought his first new truck a glider kit so he could still use the fuel efficient 60 series Detroit.

David Oster started going to the woods with Jay early on, and took every chance he could to jump in the log truck with Dad.  I remember giving him his first hardhat on a job in 2007 when I ran into him and Jay on a logging job.  His little brother Jay Jr (JJ) joined the family in 2000; it was also this year that Jay and Rhonda officially tied the knot.  Both boys were just like dad, always wanting to be in the woods.  “When we were at logging camp Rhonda would pack us a bunch of food; they would eat it in two days.  Then they would move on to the rest of the crew because I don’t cook! Their ultimate goal was to go to town and get dinner with Brad. He really spoiled them!” Jay remembers.

Jay continued hauling for Osler until Brad retired in 2018 and Osler Logging moved their efforts towards the excavation business.  Jay also decided to try the gravel game and when he ordered his next new truck it was a gravel hauler.  This was not for Jay “could only work 10-12hrs a day!  Only half a day!” he says!  After 3 months he called Lee Wilhem who with his shop and knowledge they converted the brand-new dump truck into a log truck in four days.  This was when Jay started hauling for other contractors including Sun Mountain Logging and any contractor with wood to move.  “I am known as an Old Wood Whore” Jay chuckles. 

In 2021 Jay expanded his business and added an employee and a short logger log truck.  This was in reaction to the need to haul short logs in a more efficient fashion.  Jay and his eagerness to figure out ways to dump the most wood have ended up with some interesting log truck axle configurations that work well.  

Jay credits his business success to always looking ahead and finding something to do including one bad breakup where he was back to falling timber on the west coast when Montana was shut down.  “Always look ahead and plan; be ready when you think this job will get rained out, find another spot to haul that will be dry!”  

JJ was the first to join the company in 2023. He had loaded logs one summer for CR Logging and had a successful career with Pacific Steel but wanted to get back to the woods.  He got Jay’s old truck and Jay got a new T880.  A few months later in early 2024, David also came to work for the family business. David also had a good job with Pacific but it was time to get back to the woods.   He was spoiled a few months later with a new truck, then they added one more new truck getting the fleet up to 4 new trucks. 

David and his wife Shaylyn Schott’s son Gavin, is a chip off the old block and like his dad, is eager to be out in the woods riding with dad or grandpa.  His little sister Charlotte (Charlie) is too and my guess is she will be hitting the woods soon, as it is a family tradition!  Both also enjoy shop time turning wrenches with dad and grandpa.

You would have to look hard in Montana’s logging and log hauling community to find someone who does not know Jay and his boys.  Their good names come from work ethic and a can-do attitude that it takes to go from sweeping sawdust in a sawmill to owning a successful trucking company with 5 trucks, 2 loaders and several nice shops.  If I was a betting man my money would be these timber roots have not stopped growing!  It will only be a matter of time before we will be seeing Gavin and Charlie out in the woods riding for a while and before we know it, they will be driving those nice Jay Oster Trucking trucks with lots of axles and a huge load of logs!