It's commonly accepted that five years after Derek Jeter announces his retirement that he will be inducted in to the Baseball Hall of Fame. He is the Yankees' all-time leader in games played, at bats, hits, and stolen bases.
If we can agree that Jeter is a surefire Hall of Famer, then we can compare players to him to see how they stack up. Luckily, Bill James has already done this with similarity scores. According to this metric, the player most similar to Derek Jeter is....Craig Biggio.
Biggio received 68.2% of votes in his first year on the ballot, the highest percentage of any player last year. It wasn't enough to get him elected (75%) and it is uncertain if his support will improve with an influx of deserving players this year coupled with the logjam of suspected PED users that will remain on the ballot for years to come.
I believe the difference between the two players comes more from narrative than it does from statistics. Jeter's Baseball Reference page shows nicknames as "Captain Clutch" and "Mr. November." Biggio's page lets us know that his middle name is Alan. Jeter is the heart and soul of the most prestigious team in baseball and is a 5-time World Series champion. Biggio got hit by pitches a lot, played a few different positions, and was good friends with Jeff Bagwell.
Biggio doesn't have as many Gold Gloves or All-Star appearances as Jeter. Both of those awards are voted on by fans and/or the media, so to use those factors to belittle Biggio would be basing your present vote on others' past voting which seems asinine to me.
Last season, Derek Jeter was 39 years old. This chart shows the average season for both Jeter and Biggio through age 39.
You will notice that the average WAR for each player is nearly the same despite each of Jeter's "slash" numbers holding the advantage. The reasoning is twofold. Biggio was the more durable player and more games equates to a higher WAR if you are above replacement level. Secondly, Jeter's poor defense (which is best documented here) has helped narrow the gap.
Biggio's defense netted a -2.2 WAR through his age 39 season while Jeter is a career -9.2 WAR defensively thus far. I admit that cutting off the last two seasons of Biggio's career helps his defensive numbers but it is beyond safe to assume that Jeter's defensive numbers will continue to be below replacement level. He has a -2.9 dWAR over his last three seasons, one season of positive dWAR since 1999, and is coming off multiple lower body injuries. Unless he DH's more or switches positions, his defense will continue to diminish his overall value.
Many Biggio detractors claim that he was never a dominant player while playing. The best season of his career was in 1997 when he finished with a 9.4 WAR, good for second in the NL. His best 7-year span accumulated a 41.6 WAR. Jeter's best season was in 1999 when he finished with a 8.0 WAR, good for second in the AL. His best 7-year span accumulated a 42.3 WAR. To recap, Biggio's best season was more valuable than Jeter's and Biggio was less than a win worse than Jeter over their best 7-year spans.
Before you think I am going on an "I hate Jeter" onslaught of his career, re-read the first paragraph. I believe he will and should be a first ballot Hall of Famer. I think he would be unanimous if it weren't for writers who refuse to vote for anyone in their first year of eligibility. Derek Jeter is one of the best players to ever play baseball, and I am not attempting to disparage that sentiment. I'm attempting to determine why the perception of these two players is so different when their statistics suggest they are very similar.
So what is the biggest difference between these two players? The postseason. Jeter has a plethora of postseason moments that are burned into our memory. From the flip play in Oakland to the Jeffery Maier home run, Derek Jeter has been a prominent player in October for over a decade. All of this makes for a great story, and writers love stories. When it comes time to vote for Hall of Famers, writers will value Jeter over other players, because his story is better than most, including Biggio. And that's without even knowing the ending yet.