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.



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Alex is a writer for FanGraphs and The Hardball Times, and is a product manager for The Washington Post. Follow him on Twitter @alexremington.


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MAC
Member
MAC
3 years 8 months ago

Neal Huntington.

Slats
Guest
Slats
3 years 8 months ago

Harry Frazee for selling the best player in baseball to a rival team so he could use the money to produce theatre plays.

This instantly makes him the worst owner in history.

Slats
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Slats
3 years 8 months ago

For those of you don’t know your history: Frazee sold Babe Ruth to the Yankees for $500,000

Soxfan-1966
Guest
Soxfan-1966
3 years 8 months ago

And this is a total falsehood. In truth, Frazee sold Ruth because Ruth was a highly-paid prima donna who was holding out for even more money. Frazee saw Ruth as having a bad attitude and a tendency to get into trouble, so he decided to rid himself of a potential bad influence upon the team. That he sold him to the Yankees was the result of a lot of internal politics and the soured relationship between Frazee and Jacob Ruppert (one of the NY owners) and Ban Johnson, the AL President.

Chummy Z
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Chummy Z
3 years 8 months ago

Who is the Babe Ruth you speak of?

Colin
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Colin
3 years 8 months ago

It was $125,000 cash and a $300,000 mortgage on Fenway, just to be clear.

KG
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KG
3 years 8 months ago

Chummy Z:

the sultan of swat!
the king of crash!
the colossus of clout!
the colossus of clout!
the great bambino!!!

Jim
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Jim
3 years 8 months ago

O’Malley STILL makes millions of people furious just hearing his name. There’s no argument for anyone else being as hated in baseball by as many people as him.

baseball
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baseball
3 years 8 months ago

Huntington isn’t an owner.

Peter Angelos
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Peter Angelos
3 years 8 months ago

Hello!!!

Radivel
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Radivel
3 years 8 months ago

While this is a baseball blog, you did expand to other sports anyway, and so I’m a bit surprised that Robert Irsay didn’t get a mention: http://en.wikipedia.org/wiki/Baltimore_Colts_relocation_to_Indianapolis

Imagine waking up the next morning to realize that the team you’d known and loved forever was suddenly now playing in Portland.

The Seattle Supersonics were also not handled very gracefully, to say the least.

Dolans
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Dolans
3 years 8 months ago

Some would say me.

TheHoustonian
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TheHoustonian
3 years 8 months ago

The Robison Brothers immediately come to mind. For those who don’t remember 1899 (and who among us doesn’t remember 1899?), the Robison Brothers owned the Cleveland Spiders. They then bought the St. Louis Browns, changed their name to the Perfectos, and transferred all of the Spiders’ best players (including Cy Young, Bobby Wallace, and Jesse Burkett) to the Perfectos, who played in a more populated city (read: better attendance and more money.) They also shifted a lot of Cleveland’s home games to the road, including their Opening Day game, which was held in St. Louis.

Mike
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Mike
3 years 8 months ago

Clay Bennett and Howard Schultz are the worst owners in the history of pro sports.

Joe Mauer's Silver Slugger
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Joe Mauer's Silver Slugger
3 years 8 months ago

Supported by a slimy commissioner.

Ryan D.
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Ryan D.
3 years 8 months ago

John McMullen of the Astros was a real dandy. Wouldn’t spend money to keep a “washed up” Nolan Ryan while funneling money “he didn’t have” to the NJ Devils.

chuckb
Member
chuckb
3 years 8 months ago

And still, Drayton McLane was much worse.

Hal Jordan
Guest
Hal Jordan
3 years 8 months ago

Nope. McLane was definitely not worse than McMullen. That statement makes me wonder if you really remember McMullen and all the things he did or if you’re only old enough to remember McLane’s tenure as owner.

Gadwin
Member
Gadwin
3 years 8 months ago

No mention of David Glass?

Eric
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Eric
3 years 8 months ago

As a Ranger fan, I just want to give a big ol’ F you to our old pal Tom Hicks.

A different Eric
Guest
A different Eric
3 years 8 months ago

I agree to an extent, though at least he let JD put a plan in place to start rebuilding the farm and improve the scouting department. But yeah, he was pretty bad.

A different Eric
Guest
A different Eric
3 years 8 months ago

It was – he was horrible when he was interested, but basically turned over the keys to Jon Daniel and, thereafter, Nolan Ryan. Much of the team in place now traces its roots to the Hicks era, though he mainly contributed by staying out of the way. After the Arod and Chan Ho debacles, that is.

Canard
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Canard
3 years 8 months ago

Harry Sinden and Harold Ballard.

Canard
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Canard
3 years 8 months ago

Whoops that should read Jeremy Jacobs, not Harry Sinden.

dasein
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dasein
3 years 8 months ago

“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.”

She was also notoriously cheap (did not even throw the Reds a celebration party when they won the World Series), astoundingly regressive when it came employee discipline (possibly firing Davey Johnson because he was living with his fiancee before they were married), and let her dogs shit all over the field before games. If she hadn’t kept ticket prices so low, she’d probably be a slam dunk for worst owner of all time.

And it’s pretty generous to call someone’s support for Hitler “putting their foot in their mouth.”

chuckb
Member
chuckb
3 years 8 months ago

Not to mention the horrendously racist manner in which she referred to stars Barry Larkin and Eric Davis. Many of the creatures mentioned here were just bad owners. She was a despicable human being.

Ben
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Ben
3 years 8 months ago

Never heard about this. What did she say?

B N
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B N
3 years 8 months ago

Wikipedia seems to have a pretty good accounting of her various incidents. In this case, it was calling black players on her team “million dollar n*ggers.” Apparently, she also stated that she didn’t understand why the term “Jap” was offensive.

Owning an old Nazi armband and making anti-Semitic comments were just the last straw. Words for the wise: if you’re thinking of starting a phrase with “Hitler wasn’t so bad at the start, he just got a little carried away” it’s probably best to just keep that to yourself… and uhm… do some deep personal reflection.

iallm
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iallm
3 years 8 months ago

glass ran the royals into the ground for ten years and then bought em for a song.

And has pent the last 20 years driving them underground.

Balthazar
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Balthazar
3 years 8 months ago

I’m surprised at no mention of Charles O. Finley so far. He collected a remarkable assemblage of talent, and his teams are the epitome of performance over flash. But he was personally despised, with cause, by everyone of his employees and everyone who had business dealings with him. He broke every ‘unwritten rule’ of dealing and ettiquete for an owner in his time, and was literally at war with the Comissioner’s office on a weekly basis. Having built a valuable franchise, he didn’t understand a _thing_ about asset appreciation and torched his asset’s value by his incredible obsessions with cash flow. He was the cheapest man alive: I’m sure that in a cheap-out against Comiskey and Schott, Charles O. Finley would win, not least because it seemed a point of honor with him, nay a raison d’etre, to shave the surface off an nickle he was forced to surrender to meet the most basic expenses.

Finley is a fascinating figure. I have no doubt that he would win as the most _despised_ owner. Whether that is the ‘worst’ is another question, but clearly Charlie O. is in the running.

stickman
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stickman
3 years 8 months ago

Finley was a disaster for his franchise. When he left Kansas City, Sen. Symington (D-Mo) called Oakland the “luckiest city since Hiroshima.”

In Oakland Finley produced 3 World Series titles. But how awful an owner was he? So bad that his amazing string of on-field success failed to build even a mediocre fan base in the Bay Area.

After 10 years of listening non-stop to Finley disparage his players, managers, fellow-owners, franchise history (one day, he threw most of the old Philadelphia Athletics memorabilia into a dumpster), and fans, Northern California helped Finley set a modern attendance record in 1979. Less than 400,000 fans total showed up for the season, most of them on half price Mondays.

Finley’s response was to try to move the team to Denver.

Balthazar
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Balthazar
3 years 8 months ago

I lived in Oakland in 1979 and _went_ to some of those games. The team was somewhat fun to watch, but being there with a couple of thousand folks was . . . interesting. Nowadays, I’d boycott a team like that, but I was young then with a lot of time on my hands.

Finley was really a despicable man, and treated everyone equally—BADLY. It’s possible that the Robinson brothers cited above were even worse as _owners_ in terms of the damage they did to the franchise and city involved, but as a person I can’t see how Charles O. Finley could lose a ‘worst owner’ evaluation. The only person I know of in any sport who could compete with him would be Ernie Shore, the hockey player and owner. Vicious, mean-spirited, miserly son-of-a-rat; knew the game, but that’s small compensation.

orangefiftysix
Guest
orangefiftysix
3 years 8 months ago

I just want to throw Robert Sarver’s name out there (owner of the Phoenix Suns) for repeatedly ordering management to trade away first round draft picks for cash considerations and to save additional cash by avoiding the rookie contracts. Notable players sold off: Rajon Rondo, Luol Deng, and Rudy Fernandez. Not exactly a Mt. Rushmore of NBA’ers, but a trio of talent that certainly would have gone a long way to helping put his team over the top. Oh, and then he traded the face of the franchise, Mr. Steve Nash, to their hated rivals. Sarver’s meddlesome efforts certainly enter him into the conversation.

big league chyut
Guest
big league chyut
3 years 8 months ago

As a Suns fan, I’ll second that. I’ve had my qualms with Diamondbacks ownership in the past, but when I think of bad ownership in Arizona sports I think of Sarver.

Pirates Hurdles
Guest
Pirates Hurdles
3 years 8 months ago

Kevin McClatchy – financial mismanagement costs your best player (AmRam), no funding for the amateur markets, terrible front office hirings, misuse of revenue from a new stadium. Overall dragging one of the game’s top franchises into an embarrassing pit of despair that is taking years to climb out of.

maqman
Guest
maqman
3 years 8 months ago

Hicks qualifies in two sports as owner of the Rangers and Liverpool in the English Premier League. Heartily hatted on both sides of the pond.

Bill
Guest
Bill
3 years 8 months ago

Giles of the Phillies, he single handedly destroyed the Phillies mini period of WS contenders from 75-81 with his miserly ways, made even more assinine by the fact that he claimed poverty by running a team in the 4th biggest market in the country.

Naimoli of the Rays was awful as well, maybe under the radar by he was cheap AND a meddler AND he had a knack of ‘connecting’ with fans. Google Naimoli and altercations and you can come up with a whole laundry list.

stan
Guest
stan
3 years 8 months ago

I’d like to cast a vote for Steinbrenner. I’m sure Yankee fans have some affection for him because he b(r)ought them some winners, but his character couldn’t be lower, he was a classic meddler, and oh by the way, he single-handedly created the inequity in spending that we are still dealing with today by unabashedly blowing away all salary boundaries. Until Steinbrenner came along there was at least some decency when it came to parity and spending. After he came along suddenly payroll is the first thing you look at to determine which franchises are going to have sustained success.

Radivel
Guest
Radivel
3 years 8 months ago

Dollar Bill Wirtz crushed the Chicago Blackhawks for ages by never agreeing to local TV or radio broadcasts for reasons I can’t remember. His son is doing far better.

Tommy Lasordas Pasta
Member
Tommy Lasordas Pasta
3 years 8 months ago

Rachel Phelps – baseball = Georgia Frontiere + football

Although I hate her, I wouldn’t say she is the worst owner ever. My most hated is McCourt, although I totally admit I am completely biased.

Baltar
Guest
Baltar
3 years 8 months ago

Yes, baseball “punished” McCourt by making him sell his team for a $1 billion profit.
Punish, me, baseball, punish me.

B N
Guest
B N
3 years 8 months ago

I think there’s just no way to integrate “worst owner as a person” and “worst owner for the team” into a single measure. I’d say we should just think of those as separate lists. That would be interesting as we’d end up with a nice 4 quadrant chart of owners, to see who was good despite being a pretty terrible person and whose ownerships were horrible, despite their generally good natures.

Breaking those down, I’d say we’d get these sort of characteristics in each:

Bad Person – Racism, personal attacks, cruel to subordinates, lies, fraud, immoral sources of money

Bad for Team/Fans – Poor spending, unwilling to spend, hurt signing/retaining players (e.g. racism, feuding, etc), moved team, poor facilities (stadium, etc)

Those seem like many of the typical issues we see out of owners, though definitely not an exhaustive list.

B N
Guest
B N
3 years 8 months ago

Of these traits, I’d probably list racism as the worst overall as it spans both lists (bad as a person and bad for a team). Then again, I’m a Red Sox fan who is aware that if carpetbagging Yawkey hadn’t bought the Red Sox we could have had Willie Mays and Jackie Robinson… sharing an outfield with Ted Williams. Not like THAT team would have won a championship or anything…

Joebrady
Guest
3 years 8 months ago

I can’t beleive no one has mentioned a certain basketball owner, who actually has a rule in the rule book named after him.

pat rocket
Guest
pat rocket
3 years 8 months ago

Al Davis gives Oakland two of the all time worst.

Joebrady
Guest
3 years 8 months ago

As a Raider fan, I take exception to this. Davis obviously stayed on way too long, but for almost 40 years, Oakland was as well-run as any organization in FB.

Dave in GB
Guest
Dave in GB
3 years 8 months ago

Bob Irsay. Any Baltimore sports fan would take turns on this guy, and any loathsome owner (i.e. Angelos) will be compared to him in the mid Atlantic area.

garrett hawk
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garrett hawk
3 years 8 months ago

Stepian was mentioned. Is there another?
-Yawkey to Red Sox front office guys who were giving Jackie Robinson a tryout: “Get that N—off the field!” Tough to top that, and it’s got to be especially sickening to Boston fans of that era, because the Red Sox were repeatedly only a game or two away from the pennant. And does the Splinter get walked nearly as often if Willie Mays and Jackie are hitting behind him for a dozen years?
-Finley was cheap as hell, but was he personally evil? I know that the other owners detested him, but that was because he was trying to bring the game into the 20th century, and the other old dudes didn’t like that. Eventually, many of Finley’s ideas were instituted, and were successful. And you have to admit, he built one hell of a baseball team in the early 70’s.

Jon W
Guest
Jon W
3 years 8 months ago

How in the world has no one mentioned Peter Angelos? A spendthrift meddler if there ever was one. Since the O’s had the top payroll in baseball in 1998 they’ve never eclipsed that mark, while overall salaries in the game have doubled or tripled. He fired Davey Johnson the day the won manager of the year. He fired Jon Miller because he wasn’t enough of a homer. He presided over 14 consecutive losing seasons, broken only by a miracle year with a team of nobodies and castoffs. He tried to hire four or five top GM candidates last offseason, only to be told “no, I’d rather have a lesser position and be paid less by another organization than a raise and a GM job working for Angelos” by all of them. He forced a trade of then top prospect Denny Bautista after a single bad debut outing, resulting in the acquistion of journeyman reliever Jason Grimsley (who then outed half the team in the steroid scandals). Angelos inherited a reasonably competitive organization with a wonderful new stadium that was sold out every night, and in 20 years turned it into a laughingstock with a stadium that only filled up with Yanks, Sox, and Phils fans.

The best case for 2012 Manager of the Year for Buck Showalter was that he was able to guide an Angelos-owned team to 93 wins.

Marver
Guest
Marver
3 years 8 months ago

As a Clippers, Padres, and Chargers fan, I feel like I have sufficient ‘worst owner’ experience to place a vote: Jeff Moorad.

Not only was he a ridiculous miser — league low payrolls, no ballpark improvements, constant new uniforms — but he also let fan favorites leave (purchase precipitated the Peavy trade, Adrian), failed to sign Karsten Whitsen, and even meddled in GM affairs (allegedly signing Orlando Hudson in SD and, famously, Eric Byrnes in AZ). He also saddled the franchise with a ridiculous contract on Josh Byrnes which basically guaranteed he stayed for another half-decade, after letting Jed Hoyer leave for absolutely nothing. Not to mention that he looked like Bob Vila sans ‘Just For Men’ throughout the entire process.

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