The Home Run Derby is baseball’s real midsummer classic, a spectacle of brawn and nerve that pits eight of the game’s most fearsome mashers against a series of slow-pitched gopher balls—and each other. The Derby is capable of turning the next night’s All-Star Game into something of an afterthought. Ball after ball arcs straight into nothingness, as the daunting geometry of the baseball field is conquered with satisfying repetition—61 times, fittingly, a full Roger Maris season of home-runs, during Yankee Giancarlo Stanton’s record-setting Derby performance in 2016.Tonight’s Derby will make history even if Stanton’s record survives: For the first time, two Jews will share a bracket in the single-elimination tournament. Astros infielder Alex Bregman, one of the young stars of their 2017 World Series-winning club and last year’s all-star game MVP, will face off against Dodgers center fielder and World Baseball Classic Team Israel alumnus Joc Pederson in the competition’s first round. A member of the tribe is guaranteed to make the final four of the Home Run Derby, and the winner of their matchup can plausibly claim to be the greatest Jewish slugger of all time.Really? Imagining that either Bergman and Pederson is a lock for the Hall of Fame is certainly at stretch at this point in the young careers of either player, though Bregman at least is already a bona fide star. It is also true that while Hall of Fame Detrout Tigers slugger Hank Greenberg won two MVP awards and hit 58 home runs in a single season, he played in a time before frequent triple-digit fastballs or metrics-driven infield shifts. It’s just a different game these days.It wasn’t such a different game when right-fielder Shawn Green hit 328 career home runs in the 90s and early 2000s, most notably for the LA Dodgers. Green played in the most home-run happy era in baseball history, and was overshadowed by, among other players, Barry Bonds, the power-hitting terror for the rival San Francisco Giants’ who briefly appeared to have broken the entire sport. Green did nothing of the kind, but he still finished sixth in MVP voting in 2001 – without the apparent aid of steroids. The Dodgers star also had a sense of Jewish responsibility that earns him special consideration, at least here: Green sat out on Yom Kippur in the midst of a playoff race during his also-ran MVP season, breaking a 415 consecutive game streak and hearkening to Dodgers icon Sandy Koufax’s recusal during the 1965 World Series.While we’re on the subject of atonement, Jewish slugger Ryan Braun accomplished something Shawn Green and every other Jewish ballplayer of the last half-century never could. In 2011, the Brewers left-fielder earned the National League’s most valuable player award, recompense for a season in which he either led or placed in the top five of every meaningful offensive category, advanced as well as traditional.With 334 career home runs and counting to Greenberg’s 331 and Green’s 328, Braun is unquestionably the most productive Jewish home run hitter of all time–except for the asterisk attached to some of those numbers. In 2013, Braun admitted to using steroids during the 2011 season, which resulted in about a 9-week suspension. The revelation that a recent MVP and likable superstar-in-the-making was in fact a steroid cheat kicked off another round of a then-15-year-old argument about the possible chemical vandalism of the national pastime. The year 2013 seemed like a curiously late point to be re-adjudicating steroids, and by then everyone just wanted the whole discussion to be over. When Braun was reinstated in the spring of 2014 baseball fans were more or less happy to ignore the guy, rather than feigning outrage or buying into an easy narrative of moral rehabilitation.The still-active Braun’s career stats are gaudy, and he had a probably non-steroidal all-star season in 2015, but the blot on his record is big enough to disqualify him from All Time Greatest Jewish Slugger consideration. He’s an MVP, yes, but also a microcosm of some of the worst things about his era of the game, and perhaps a reminder to Jews that we aren’t really so special.Could the greatest Jewish slugger be someone who’s semi-obscure in our own day and age, at least to people who aren’t Cleveland Indians fans? Al Rosen set the American League rookie home run record after clubbing 37 dingers in 1950 and was one percentage point short of the 1953 Triple Crown (Mickey Vernon edged him out for the batting title, .337 to .336), a season in which he smacked over 200 hits and led the league in runs, slugging percentage and on-base percentage-plus-slugging, a feat that only he and Hank Aaron have ever achieved. In addition to the ‘53 AL MVP, Rosen had racked up four all-star appearances and roughly 30 career wins above replacement before injuries derailed what would have been a Cooperstown-worthy career in his early 30s.Like Greenberg, there’s no real way of knowing how peak Al Rosen might have done against modern-day pitching, but he had a good enough baseball mind to make it as a GM with the Astros and Giants, winning executive of the year for the latter club in 1989. Rosen in his prime might well have figured out a way to beat a time-traveling Max Sherzer or Clayton Kershaw. But time travel is a riddle science has yet to crack—in a debate over who the greatest Jewish slugger of all time might be, Monday’s as good as a place to start as any.For stat heads keeping score at home, Tablet has compiled a bracket pitting the winner of the Bregman-Pederson show-down with three more Jewish slugging contests that would have been worth paying admission for: Braun versus Green, Al Rosen versus his similarly underrated peer, second baseman Sid Gordon (a 1950s version of modern-day slugging Jewish second baseman Ian Kinsler) and Hank Greenberg versus his Jewish neighbor in Cooperstown, star Cleveland Indians shortstop and player-manager Lou Boudreau.The winner of this trans-historical contest will receive the Lipman Pike Trophy, named for baseball’s first great Jewish slugger, the forerunner of Babe Ruth, who once hit six home runs in one game, a record that has never been equaled by anyone—Jewish or not.