But now, 63-year old Terry Sims is as close as anyone has ever been to capturing the coveted $5.6 million grand prize.
Sims, an Arizona resident, made Beat the Streak history Saturday evening when he picked Houston second baseman Jose Altuve to extend his exhilarating run. Altuve went just 1-for-5 in Friday night's 13-run explosion by the Astros, but doubled in the first inning Saturday against Kansas City. That ran Sims' streak up to 49 games, tying Mike Karatzia's 49-game string in 2007 for the longest single-season run in BTS history.
Sims is now just seven games shy of DiMaggio's mark and an impressive 86 percent of the way toward the ultimate goal of becoming the first grand-prize winner in BTS history. He admitted he had never before had a streak go past 20 games, and remained humble in his reaction to tying the BTS record.
"Hard to believe it is me," Sims said in an email to MLB.com. "Just trying to keep the same routine and hope for the best. I'm picking guys who are good hitters and not facing the ace of the opposing staff."
A look at both DiMaggio and Sims' streaks through 49 games reveals that Sims has arguably had a less stressful time getting to this point. Sims' players have skirted by with a single hit 24 times, while DiMaggio survived with a single hit in 32 of his first 49 games of the streak. Additionally, Sims' players have entered the final plate appearance needing a hit four times -- including twice by Altuve -- in the first 49 games, while DiMaggio came down to his final plate appearance seven times in that span.
"This is crazy!" Sims said. "Don't know how many thousands [of people have played] BTS this year, but to be on top is amazing."
The current leader works a couple days a week at Antelope Hills Golf Course in Prescott, Ariz. -- a part-time job that "keeps me out of trouble," he joked -- and said he hasn't employed many advanced statistics to help him keep up his record run.
"I am not your typical baseball nerd," said Sims, a former D-backs season-ticket holder. "I can't recite stats like some guys can."
If he does win the multi-million dollar grand prize, the retired candle maker said his current plans for the money are fairly modest.
"Our AC just went out," Sims said. "So if I win some money, Mike Little and the boys at Chino Valley Heating and Cooling will be happy we can pay for the new unit."
Through Beat the Streak, participants try to establish a virtual "hitting streak" by picking one or two big leaguers per day, with their run continuing as long as their selections collect at least one hit in that game. In 15-plus seasons of BTS play, no one has matched DiMaggio's magic number of 56, set in 1941. To win the grand prize, one must top Joe D.'s run by one.
Even if Sims happens to fall short of the grand prize, he has put himself in prime position to claim the $10,000 consolation prize given to the player with the highest streak should no one break DiMaggio's mark. Additionally the BTS game makers hand out millions of other prizes for streaks as small as five.
Better yet, it's easier in 2016 than ever before to make a run at the Yankee Clipper thanks to features like the "Double Down" option. With Double Down, fans can advance their streak by two games by picking two hitters in the same day. If one goes hitless, however, the streak ends and the BTS player's total returns to zero.
Furthermore, BTS players now have a wealth of other research filters at their disposal including batting-order position, right- or left-handed pitchers and cold opposing pitchers. They can even take days off when they don't see any matchups that are favorable -- so long as they exceed 56 by the end of the season.
It would be only be right if Sims or another BTS user could break the BTS drought this year. After all, it's the 75th anniversary of DiMaggio's remarkable streak, which is being commemorated with daily recaps on MLB.com and @TheStreak on Twitter.
Matt Kelly is a reporter for MLB.com based in New York. Follow him on Twitter at @mattkellyMLB. This story was not subject to the approval of Major League Baseball or its clubs.