I'd vote for Theo, Beane, Sabean, and Bob Watson, Cashman's predecessor at MFY from 1995 through 1998 and the first black GM to win a WS.
Probably not Cashman, who I view as having largely coasted on the core homegrown HOFers he was gifted and then bought the all-star-du-annee free agent every year, and thus far it's worked once in the last 22 years. Let them put him in the MFY HOF as a lifetime achievement award, but really it's just a longevity achievement award. He takes few real risks, and the results have been "fine" given the resources at his disposal.
If I'm only allowed to vote for one of those 4, I think I squint and say Theo. I think a lot of non Boston / Chicago fans would agree with his resume above the others. But in general, while I want the Hall to be mostly about players and less about guys who (let's be honest) mostly get to their position on old-boy-network cronyism, I think there's room for an executive every 2 years or so. Here are the current counts of inductees:
236 MLB Players
35 Negro League Players
31 Executives / Pioneers (of which 5 were in 2006 for the select committee on the negro leagues)
22 Managers
10 Umpires
That ratio doesn't seem too whack, but here's who's gotten in as an executive / pioneer, other than that 2006 SCNL group, in the last 40 years:
- 1991 Bill Veeck, owner of the Cleveland Indians, St Louis Browns and Chicago White Sox, and who signed the first black player in the American League
- 1995 William Hulbert, the 19th century owner of the Chicago White Stockings and basically the founder of the National League
- 1998 Lee MacPhail, part of a MLB dynasty (his father Larry was also inducted), never an owner, rarely a GM, was president of the AL, but doesn't seem to have done much that was notable other than know everyone and be in baseball for a long time
- 2008 Bowie Kuhn, commissioner 1969-1984, ended the reserve clause but only under duress and after taking it to the Supreme Court, didn't do anything all that great, but was a big part of baseball's history
- 2008 Walter O'Malley, Brooklyn/LA Dodgers owner 1950-1979, the guy who moved them to the west coast after Robert Moses screwed him. Squeezed out Branch Rickey. Had a lot of political connections, made a lot of money, won a few World Series.
- 2008 Barney Dreyfuss, owner of the Pirates from 1900-1932 and creator of the World Series
- 2011 Pat Gillick, GM of 4 teams for a total of 30 years, won 2x WS with Toronto and then in 2008 with the Phillies
- 2013 Jacob Ruppert, owner of the Yankees from 1915-1939, establishing them as the premier dynasty in the league
- 2017 John Schuerholz, GM of KCR 1981-1990 the Braves 1990-2007, President of the Braves 2007-2016. Won 1985 and 1995 WS, had what you could consider a dynasty in Atlanta
- 2017 Bud Selig, because all commissioners must be hall-of-famers, just by Great Man theory
- 2020 Marvin Miller, MLBPA director from 1966-1982, won free agency and a bunch of other victories for the players, changed the game. Literally inducted only over his dead body.
- 2022 Bud Fowler, 19th-century player believed to be the first african-american player in pro baseball, and started a lot of pro ballclubs.
- 2022 Buck O'Neill, player and manager in the negro leagues and later its spokesperson and advocate that helped bring them to greater public awareness
A majority of them clearly deserving for being a core part of the story of baseball. A few seem a little off the pace, but were baseball lifers in positions of power (MacPhail, O'Malley, Selig), and even of those, the only one I can say that removing them from the hall wouldn't change the story of the sport one bit is MacPhail.
That's a pretty high standard. I think Theo and Sabean are probably in just on trophies won, and Watson on a combination of 1996, the dynasty that followed, and breaking barriers personally. Beane... you'd really have to squint to say that his contributions to the game stack up against some of those inductees (like, it's clear he borrowed a lot of ideas from predecessors like Sandy Alderson and just committed to them more fully), and he can't make up for that with sustained success of the teams he built; there's no wins-per-payroll-dollar trophy. Frankly, I think I'd vote for Alderson over Beane. But their admissions will play out over the course of a decade or two, and we'll have a bit more perspective as that goes.
