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NASCAR Chase race 5: Milestone will inspire Dale Earnhardt Jr.

Photo: Michael Pugh/AP

Dale Earnhardt, Jr. in 1999, on the eve of his first Cup series start, which took place at Charlotte.

It was May 30, 1999, and Dale Earnhardt Jr. was 24-years-old. At the time, Barack Obama was a state senator in Illinois, Columbine High School in Littleton, Colo., had just entered the national consciousness, and Star Wars Episode 1 was about to become the highest grossing film in history.

So much has changed in American life and culture since the son of the Intimidator, the seven-time NASCAR champion, made his first Cup start 14 years ago at Charlotte Motor Speedway. On Saturday night at that same track where it all began, the driver once known as Little E, who celebrated his 39th birthday on Thursday, will become only the 34th person in Cup history to start his 500th race in NASCAR's highest series.

GALLERY: Classic photos of Dale Earnhardt Jr.

For the last 10 years Earnhardt has been voted by fans as the sport's most popular driver, yet in none of those seasons has he won the championship. He's been good -- Earnhardt has 19 career victories -- but not great. Which raises the question: Can he do it this year?

It won't be easy. His title chances appeared doomed after he suffered an engine failure in the Chase opener at Chicagoland and finished 35th, but since then he came in sixth in New Hampshire, second at Dover, and eighth at Kansas. With six races left in the playoffs, Earnhardt is eighth in the standings, trailing leader Matt Kenseth by 54 points. It's not an insurmountable deficit, but it's very close to it. The only way for Earnhardt to make a charge at the championship is to win multiple races over the next six weeks and hope that the likes of Kenseth, Jimmie Johnson and Kevin Harvick struggle.

Earnhardt should be fast on Saturday night at Charlotte. On Thursday, he qualified sixth. But because of where Earnhardt sits in the standings, he and his crew chief, Steve Letarte, can afford to gamble -- both on the track and on pit road. Races at Charlotte often boil down to games of fuel mileage, so expect the number 88 team to try to pit out of sequence or stretch their fuel in order to steal a win.

Back in his Cup debut at Charlotte in 1999, Earnhardt finished a respectable 16th. In his 26 starts at the 1.5-mile track since then, he has yet to win, but he does have five top-five finishes.

Darrell Waltrip tweeted on Thursday that he believes that Earnhardt, recognizing the symbolism of this race, will take the checkered flag on Saturday night. I agree. He's my pick to win Chase race No. 5 of 2013.

Here are four other drivers to watch when the green flag waves in the Queen City:

1. Matt Kenseth

Kenseth has won more races this season (seven) than any other driver. He took back-to-back checkered flags to begin the Chase, but he struggled last Sunday at Kansas -- another 1.5-mile track -- and wound up 11th. He now has a three-point lead in the standings over Jimmie Johnson.

In his last three starts at Charlotte, Kenseth hasn't finished higher than 10th. And even though his setup was off last Sunday, he has flourished on intermediate-length tracks throughout his 14-year Cup career. He was a rookie with Earnhardt in 2000, and since then the two have remained close friends. I think he'll be right on Earnhardt's rear bumper when the checkers wave on Saturday night and wind up second, solidifying -- at least for one more week -- his hold on the championship lead.

2. Jimmie Johnson

No driver in the last decade has been more dominant at Charlotte than Johnson, the five-time champion. In 24 career starts at the track, he has five wins. But there's a caveat: He has only one victory at CMS since 2006.

Still, he was oozing confidence on Thursday when he met with reporters in the infield media center and spoke about his title chances. "We've been very consistent," Johnson said. "We've been competitive. We've won a race [at Dover]. I feel good with that. I know if we keep this pace up, we'll definitely be a contender come Homestead."

Agreed. Though I don't believe Johnson will win on Saturday night, he remains my pick to be hoisting the big trophy at Homestead on Nov. 17.

3. Kevin Harvick

Relatively quiet for most of the season, Harvick emerged as a legitimate title contender last weekend at Kansas, as I wrote earlier this week. After capturing the pole, he led the most laps and took the checkered flag. He's now third in the standings, 25 points -- essentially the equivalent of 25 positions on the track -- behind Kenseth.

"Last week went about as well as you could write it down on a piece of paper for us," Harvick said on Thursday. "Sitting on the pole and winning the race is a little bit out of character from what we have done in the past. But I think for us it gives us a lot of confidence in the things that we can do and need to do to keep ourselves in position to continue to race for this championship over the next several weeks."

Harvick took the checkers in the spring race at Charlotte in May. Barring a mechanical failure or getting caught up in a wreck, he should be good for a top-five on Saturday night.

4. Jeff Gordon

If Gordon is going to win his fifth championship, he simply must -- MUST -- reach Victory Lane on Saturday night. Currently in fourth place in the standings and 32 points behind Kenseth, Gordon appears to have a very capable car for Saturday night. On Thursday, he won the pole.

Yet in his last six points-race starts at Charlotte, he has finished better than 18th only once (seventh in the fall of '12). This will be a revealing race for the 42-year-old future Hall of Famer. If Gordon flourishes -- and I think he will -- it will show that he still has the skill and the will to contend for a title. If he flounders, it could portend that his glory days are indeed behind him.

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