My Top-10 Most Hated Cubs: A Brief History of A**holes

Formerly published on Republished with author’s consent.

Ass-hats. Horrible signings. Poor play. Boo-worthy.

My list of Cubs players who warrant a spot on my personal top 10 of most hated Cubs of all time took some thought and reflection. When I whittled it down to just 10, I feel I came away with a pretty tight crew of deplorable Cubs. This is my list.

10. Todd Hundley

When the Cubs signed him, we were looking for a top-level catcher. The numbers he put up with the Mets and Dodgers were there. There was also the Cubbie blue-blood line of him being the direct descendant of one of the most loved Cubs of all time. What we wound up with was a hard-drinking, pouty, underachieving, way overpaid player.

What puts Hundley on the list is not as much the terrible play. Lord knows we’ve seen plenty of that as Cubs fans. It was the single-finger salute he gave the fans when he hit a home run during his dry spell. He tried to push it off as a shot at Reds fans heckling him, but when it smells like a turd, looks like a turd, and feels like a turd. It is, like Todd, a turd.

9. Brian McRae

Coming off some really good years with the Royals, and when the Cubs were in need of power in center, B-Mac seemed the perfect fit. Perhaps it was the fact that he played on some really lean teams. Perhaps it was his ego. Whatever. Sitting in a bar after games with Mark Grace, canoodling with the fans and ripping on your teammates will eventually come back to haunt you. And for him, it did.

Those actions were whatever. Here’s your ticket out of here. Go to the Mets. Have fun in the Big Apple.

Mac couldn’t leave well enough alone. In a showing of complete asshole-ocity, in his first game back in Wrigley, he hit a home run and was so happy with his personal accomplishment that when he crossed home, he stopped and spun his helmet on home plate. All the sportsmanship of a shart.

8. Carlos Zambrano

The only thing that doesn’t move The Bull higher up on the list is that he really had outside influences encouraging his childish behavior. From the huge contract to the culture of idiocy that permeated the clubhouse during the Dusty Baker years, he was a perfect storm.

Plunking guys. Tantrums on the mound. Fighting teammates. Retiring. Trying to unretire. The meaningless apologies. It was all ridiculous. Mostly, though, it was unfortunate. A guy with that level of talent wasted it on his own poor behavior.

7. Latroy Hawkins

“You can’t do what I do.” Need I say more?

6. Ryan Theriot

The little second basemen who couldn’t finally, after lo those many years of playing with the Cubs, found himself in the right dugout of the Cubs-Cardinals rivalry.

Then he went on to the Giants, then he went away.

And for that, we thank him.

5. Milo Hamilton

Possibly perceived to be heir apparent to Jack Brickhouse when he retired, Milo was overlooked for the job when Harry Caray left the White Sox.

The move, as we know, was possibly the best signing in the history of the Cubs, from both business and baseball perspectives, but it left Milo a bitter, sad man, who took his talents to Houston, where he sulked and scowled for years over Harry. He even dedicated an entire chapter of his autobiography to Harry, referring to him as Canary and calling him a miserable human being.

He tried to play off additional commentary about Harry following his death to an earlier interview, but none the matter. You’re not too far away from your dirt nap. And when you take it and go wherever it is we go when the heart stops beating, there will be a couple of Carays waiting to say hello.

4. Sammy Sosa

When a Hall of Famer body slams someone with true Hall of Fame numbers in his own Hall of Fame induction speech, that says something. When a teammate bashes your boombox with a baseball bat after a game, that offer another indication that something may be awry. When you are called before a House Subcommittee to talk about PED use in baseball and suddenly forget the English language, we’ve got a true smoking gun.

You would think that a player who spent 13 seasons with the Cubs would have parades for him every year. Would even be hounded like a rock star at Cubs Conventions and chuckled at with warm delight when taking the mic at some session and saying, “Baseball been vedy, vedy good to me.” Cubs fans would have been eating out of this guy’s hand for years.

Alas, all that, like his legacy and juice-up numbers are as relevant as shampoo and conditioner to John Miller.

3. Corey Patterson

Watching a guy with such promise completely and slowly come unglued was not fun. Again, I blame a lot of this problem on Dusty, who kept putting him out there, but in knowing people who lived in Corey’s building, a lot might have to do with overcoming decorating the lobby of your apartment complex in the wee hours of the morning on many an occasion and then playing most of your games during the day.

2. Milton Bradley

If you wonder how Milton Bradley could make not only my personal most-hated Cubs list, let alone that of any other MLB fan, or even just a lay person of society, you have either been asleep for a decade or really enjoy the company of ass-hats.

The signing of Milton was a good scrubbing of salt in a wound gashed open by the trade of Mark DeRosa. You get rid of a guy who was a clubhouse leader, true spirit of a solid player, and a guy who was always there in a clutch and then bring in someone with a long history of being a complete asshole on the field and in the clubhouse because of a nice dinner you had with him? What the hell was Hendry thinking?

His brief tenure with the Cubs was a slow-moving, unwatchable, train wreck, played out on the field and in the media on a daily basis. He was a cancer in the clubhouse and diarrhea on the field. And after work, as it turns out, he moonlit as a wife beater. There was absolutely not one thing about Milton, from top to bottom, inside and out, that any fan could find endearing.

This is not to say that we should idolize players, but as a player and (ahem) a role model, you have an obligation to not be the best human being to walk the Earth, but just to simply not be the worst. He buried the needle on his drive to worst.

How could Milton not be number one, you ask? Trust me, even though he may be your most hated Cub, there is truly one who found a way to rise up through the turd-filled commode to be my–and should be your–most hated Cub of all time.

And he is….

Drum roll…..

1. Ian Stewart

It really takes something to outdo Milton Bradley as my top choice for most-hated Cub of all time, but Ian Stewart went above and beyond. How so? His deplorable numbers? Nope. His slamming of the team on Twitter that led to his ultimate release? Nah, although it was Twitter (or his use of it) that puts him at the top of the list.

Ian, the social media maven he was, could almost always be found, pretty late at night, interacting with fans via his Twitter account, and he typically pulled no punches.

He would regularly berate and attack fans–me included–and even went so far as to totally hit on at least one woman I know–in the open. There were rumors of drug use and over-consumption that perhaps fueled some of these interactions, but none the matter, when you are under the employ of an organization and take to abusing and harassing their clients in your down time, that’s usually call for dismissal.

When you do so in a public forum, for all too read, you go beyond delusions of grandeur to nothing short of idiotic.

Honorable Mention

Trust me, this list could have been longer than 10. But in the spirit of baseball, here is your extended roster:

  • Ryan Dempster – Not only did he do the absolute worst Harry Caray impersonation of all time or act like a petulant child when the Cubs were trying to deal him, he was also a sexual harrasser.
  • Jack Brickhouse – Yes, the guy we and our parents grew up loving as the voice of the Cubs, Bears, and pretty much anything else WGN covered, was truly less than a gentleman. He was profane, he was vile. He makes my list for a much more personal reason. As I walked down the ramp to the upper deck behind home–before the press box as it is today–I ran into Jack walking up and asked him for an autograph. He literally waved his hand at me and said, “No. Don’t have time, sonny.” Taken aback I continued down the ramp and then thought I would give it another shot, so I turned around to chase him and found him steps from our interaction, signing for and taking pictures with a group of young, attractive women.So, congrats, Jack. You not only made this list because of that, but I’m pretty sure that at least one of those pictures is in the bottom of a cardboard box in someone’s basement with the label: DIVORCE—HERS.

So, that’s my list. Who’s on yours? @WilcoMeThat

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