I do not know anything about your horse, but I can tell you how he got his name. His sire is line bred 'Robey breeding'. Win or Lose was a very well known old stallion owed by Dick and Helen Robey back in the 70s. He was their foundation stud and was very prominent in early day breeding of reining and cowhorse competition horses. They also bred One Hundred Grand. I rode several Win or Lose horses and loved them all.
Your horse has some racing breeding on the bottom (the TB and Jet Deck) and the very bottom goes back to a very nice OLD foundation horse named Hank H sired by King P 234. Hank H sired a very famous son, Harlan, also owned by Dick and Helen. He was the most famous roping horse sire of his day.
So, you have very nice 'using' horse that is predominantly 'Robey' breeding. I would expect him to be a great saddle horse and to try to do anything you ask him to do. These were the kind of 'All around' horses we rode and raised and still do.
Here is a link to some of Win or Lose's accomplishments and get.Quarter Horse Directory - Win Or Lose
The Robeys used (help make famous) the magic cross of King / Leo / Three Bars. I wish there were more of these horses still around.