This year, he's got his money on a long shot.
The defending NASCAR champion likes Penske Racing teammate Joey Logano to win the championship.
Assuming, of course, Keselowski himself can't defend his own title.
The two Penske drivers go into Saturday night's race at Richmond trying to lock up spots in the 12-driver Chase for the Sprint Cup championship field. Logano is in far better shape than the defending champion—he's ranked eighth in the Sprint Cup standings and has one win on the season.
"Quite honestly, as it stands right now with how he's ran over the last six weeks, he would be my favorite to win the championship," Keselowski said Thursday night at Richmond International Raceway. "He's definitely got the momentum. His team has got things going for them in so many different directions. There's a lot of confidence that comes with that. He's been catching the breaks, too."
Since a 40th-place finish at New Hampshire in July dropped Logano to 18th in the points, he's been on a tear to pull himself into the title picture.
He was eighth at Indianapolis, grabbed consecutive seventh place finishes at Pocono and Watkins Glen, won at Michigan, was fifth at Bristol and was second Sunday night in Atlanta. He's not finished lower than eighth in six weeks.
Told that Keselowski liked him to win the title, Logano grinned.
"I'd be pretty stoked. It's going to be a hell of a party," the 23-year-old said. "I don't know, milk and cookies or something for me. I don't know how to party. Somebody has to teach me. I don't know how to do that. It's a big deal. It is a goal of mine, yes. It is a very big goal of mine. You strive for it every year when the season starts. I've come up short every time. This is my big shot so far in my career. Doing it with Penske Racing, as a new driver over there, it's kind of a cool story."
Especially considering Keselowski may not have a shot to defend his title.
He's 15th in points, winless and a victory Saturday might not be enough to get in the Chase. But just getting in wouldn't be enough to satisfy Keselowski.
"Any season you don't win a championship should be a lost season for every driver," Keselowski said. "I can tell you just making the Chase this year and running eighth or 10th or whatever would not have been a good year either. That's how I feel about it."