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How To Write a List of the Worst Owners Ever

Every so often, someone somewhere will write a “worst owners ever” list. It’s almost always timely, since between the four major sports there is always at least one horrendously incompetent or actively malign owner who is justifiably despised by fans. And it ticks off two key attributes for successful search engine optimization: the format easily lends itself to a photo gallery and a few casually-written sentences of snark. Most recently, there has been a glut thanks to Jeffrey Loria’s latest fire sale.

I’ve previously written about Loria and also Fred Wilpon, two of the most-criticized owners in baseball. But their perceived sins are very different. Loria has been criticized for being an unethical miser, profiting off the Expos and Marlins while keeping those teams impoverished, while Wilpon spent on his team but the Mets went broke as a result of the economic downturn and lingering fallout from the massive Ponzi scheme run by Wilpon’s friend and business partner, Bernie Madoff. So how do we determine an intellectually defensible process for making a non-arbitrary list of the worst owners in history?

First, an owner must be measured by the team he or she assembles. That includes wins and losses, it includes the pursestrings available to pursue domestic and international free agents (and to take on cash in a trade), and it also includes whether there is a team to begin with. Every owner who has ever moved a team away from a dedicated fanbase has found his way to a worst-of list.

Second, an owner must be measured by his or her involvement. Involvement can measure an owner’s responsiveness to situational need: if a team is close to contention, will that owner agree to spend a little extra? It also includes meddlesome owners who think they know about sports than the people they hire.

(Of course, Connie Mack — who owned and managed the Philadelphia Athletics from 1901 to 1950 — did know more about sports than the people he hired, but even the Tall Tactician stopped being effective after he turned 70. His teams won five World Series from 1910 to 1930, but he never finished higher than fourth during the last 17 years of his ownership and management of the Athletics.)

Third, an owner must be measured by how ethically he or she handles the business. Numerous owners, including Loria, have cried poverty or threatened to move their teams to obtain a publicly financed stadium. As Jeff Passan wrote yesterday, “This is the dirtiest secret of Selig’s two decades as commissioner: The “golden era” of which he so often brags came off the taxpayer’s teat.”

These owners have not been punished by the league. The owner who was punished was Frank McCourt, who was pushed out of baseball because he tried settle other debts by signing a sweetheart low-value TV deal that Selig determined could set a terrible precedent for others in the league.

Fourth, an owner must be measured by his or her reputation, even if it is related to off-field activities. Owners who are in frequent trouble with the law or the league office are embarrassments to their teams and their fans, not to mention to themselves and their families. This can include driving while under the influence, like Jerry Buss, or it can include allegations of “discrimination on the basis of race” in real estate, like Donald Sterling. Not all bad behavior is punished in its time — while Marge Schott repeatedly got in trouble for making racist statements, earlier owners did not — but over time, Schott and Yawkey’s reputations caught up with their actions.

Fifth, there are the intangibles. Does the owner have a horrible hairpiece or a brutal fashion sense? Is the owner in the habit of writing poorly-thought out open letters in Comic Sans? Is the owner a Russian billionaire and former presidential candidate who made his money in a shady rigged auction, who claimed that he bought an American team to improve the sport back home? Is the owner a corporation that released a red-and-black 3D console that looked like it was a prop from the show V.R. Troopers?

A miserly but hands-off owner like Minnesota Twins owner Carl Pohlad kept his team poor but did not necessarily actively prevent it from winning. On the other hand, Chicago White Sox owner Charles Comiskey was so cheap and kept his players so poor that they mutinied by taking money from gamblers — they were thrown out of baseball for life, but nonetheless, Comiskey has been retrospectively assigned some of the blame. Comiskey’s Sox won the World Series in 1917, and Jeffrey Loria’s Marlins won the World Series in 2003, but these victories were more despite the owners’ best efforts than because of them.

Reckless, meddling spendthrifts like the Washington Redskins’ Dan Snyder and the Cleveland Cavaliers’ Ted Stepien were arguably even worse for their teams. Stepien was so catastrophically profligate that the NBA had to pass a “Ted Stepien rule” to prohibit teams from trading first-round picks in consecutive seasons.

Worst of all, perhaps, are meddling tightwads like George Argyros, who owned the Mariners in the 1980s. As Neyer writes: “[H]e once decreed that his club would play the lowest average player salaries in the majors. Argyros has been mocked for telling his front office to draft Mike Harkey instead of Ken Griffey, Jr. … but that’s sort of a bad rap, since he could have demanded the drafting of Harkey, and obviously did not.”

Owners who moved their teams to a different city are often beloved in the new city and loathed in the old, like Horace Stoneham and Walter O’Malley, who moved the Giants and Dodgers from New York to California. Sometimes, the team that moves is hardly missed, like the Boston Braves: there may be some in Milwaukee who are still grateful to Lou Perini for letting them watch Warren Spahn, Eddie Mathews, and Henry Aaron, but there are hardly any in Boston who still snarl at his name. On the other hand, there are still a few people in Brooklyn who would still shoot O’Malley twice.

Racists who won championships have sometimes gotten a better shake in the history books than racists who failed to win. Tom Yawkey, the Red Sox owner who resisted integration so successfully that the Red Sox were the last team in baseball to integrate, is not well-loved outside Boston. But his contemporary Del Webb, co-owner of the Yankees during the same period, has a better reputation though he was no more progressive than Yawkey; as I wrote in July, Webb apparently used to brag that his construction company had built Japanese internment camps during World War II.

Of course, no one loves Marge Schott, even though her Reds won the World Series in 1990. But her worst crime was her inability to keep her foot out of her mouth, and lucre is usually filthier than words.

Dodgers owner Frank McCourt’s problems stemmed from the fact that he basically didn’t have the money to buy a major league baseball team to begin with. He purchased the Dodgers with a massive amount of debt financing, which came back to bite him amid his massively public divorce. Jeff Moorad tried to buy the Padres with money he didn’t have, either; after a bizarre three years of attempting to take over the team, he finally stepped aside as former owner John Moores regained control of the team.

Ethically, Loria’s crime is worse than that: Passan and others have accused him of perpetrating a massive multimillion dollar fraud on taxpayers, making a tremendous profit after driving down the value of the Montreal Expos and then securing massive public financing for a stadium in Miami, drawing SEC scrutiny in 2011. But Loria is hardly the first owner to bluff or lie his way to a new stadium funded at taxpayer expense: if owners told the truth, then new stadiums wouldn’t get built with public funds, since publicly financed stadiums are usually a bad investment.

And on, and on, and on. This is not an exhaustive list by any means. It’s more of a way of thinking about it. There are many more poor owners to come, I have no doubt, and many more of these lists will be written. Anyway, as far as I’m concerned, the top and bottom of the list should be obvious and unchanging. The best owner ever is Billy Heywood. The worst owner ever is Rachel Phelps.