I fear that today’s installment of Broadside is going to come off as an attack on Cubs general manager Jim Hendry, but that is not my intention. Rather, it's the observation that given a wait of more than a century, for the Cubs, the point is not the journey but the destination—over 100 years at sea is quite enough of a journey, thank you. And just as every team can point to their Babe Ruth or Ted Williams and say, “This is our iconic figure,” almost every organization has an executive who came along at a key moment and guided the team through a transitional period to greater heights of success, someone whose oil portrait in the office lobby bears a plaque that says, “Pathfinder.” The best the Cubs can do is hang an empty frame, or perhaps fill it with a sign: “This space for rent.”

This piece began as a look at the Cubs’ chances for this season, but as I later read back what I had written, I found that I had over a thousand words that boiled down to, “The last 102 years weren’t very good, were they?” before I even got to the 2011 team. You don’t need me to tell you that, even though there is a perverse pleasure in observing just how long it's been since the Cubs last got to celebrate a championship. The Pirates and the Royals come in for a lot of mockery, but at least you can refer to Kansas City's 1985 championship with a straight face, and bring up Bret Saberhagen, George Brett, and Dan Quisenberry as if they were contemporary humans instead of the alien subjects of 17th-century Dutch portraiture, strange, candlelit figures with ruff collars around their necks.

The Cubs aren’t that far away from us, but they’re close; bring up the last Cubs championship and you might as well be talking about the Boer War—a conflict that ended just six years before the Cubs won their last World Series. It was a different game then, played by people who we would not instantly recognize. The average height of the Cubs’ starting lineup in 1908 was about 5’9”. As good as Dustin Pedroia is, it’s hard to take seriously a roster composed of players that were not only his height but, due to their primitive conditioning, averaged 15 pounds less than him. The Cubs must cling to Tinkers-to-Evers-to Chance, but it is long since time to let these weary ghosts rest lest they see a living human the size of Prince Fielder and burst into tiny molecules of frightened ectoplasm.

Considering the long drought, it is natural to ask, “Who was responsible for this?” The Cubs may have been in stasis, but the game around them has changed, and the business of assembling strong teams should have become easier. The invention of the farm system didn’t change anything for them. The expansion of the talent pool through integration eventually brought them great players like Ernie Banks and Billy Williams, but they never could surround them with a good enough cast. The first round of the draft has been a mine field. The first blush of free agency brought them only Dave Kingman. The rise of international scouting hasn’t done much for them until quite recently—if Starlin Castro progresses as expected, it won’t be long before he can lay claim to the title of the team’s best homegrown player out of the Dominican Republic. They have often spent money—the Cubs have been in the top five NL teams in payroll every year since 2003 and in the top half continuously since 1997—but to little effect.

Sabermetrics failed them, as the Cubs didn’t learn to take a walk until quite recently, a trick they unlearned in 2010, finishing 14th in the league in passes taken. In doing so, they dropped more than 150 walks from the 636 ball fours they saw in 2008, the second-best year for walks in franchise history. In the era of free agency, only four Cubs have drawn 90 or more walks in a season (Gary Matthews and  Kosuke Fukudome once each, Mark Grace twice, and Sammy Sosa three times). The choices of manager have been desultory. The Cubs have had two Hall of Fame managers since the days of Frank Chance in Joe McCarthy and Leo Durocher, but after that, Don Zimmer.

Taken as a whole, the team's history leaves you with the strong sense that no one has been minding the store. The Cubs have been a strangely conservative organization, and I don’t just mean that they waited until September 1953 to break the color line. With the exception of Dallas Green, who built the one-shot NL East-winning 1984 Cubs with a series of brilliant trades that exploited his knowledge of a Phillies organization that had employed him for more than a decade (Bill Campbell and Mike Diaz for Gary Matthews and Bob Dernier; Ivan DeJesus for Larry Bowa and Ryne Sandberg) and despite a smattering of other deals good and bad during the free agent era (George Bell for Sammy Sosa and Ken Patterson, on the good side; Rafael Palmeiro, Jamie Moyer, etc., for Mitch Williams, etc., on the bad), the Cubs don’t seem to have been run with any kind of plan in mind since the days of Frank Selee.

That brings us to the pathfinders. Cubs general managers have run the gamut from the unknown to the obscure. The challenge of waking Sleeping Beauty in one of the country’s great cities must be one of the most attractive challenges in all of sports, but aside from Dallas Green, Andy MacPhail, and the current job holder, one would be hard-pressed to beat the Watson supercomputer at a game of “Cubs GM Jeopardy.” This is a team still in search of its Branch Rickey.

Now, you might say, “Wait a sec. Branch Rickey only worked for the Cardinals, Dodgers, and Pirates. Surely not every organization can say that it had a Rickey.” That is true—only those teams can say they had the Ur-GM himself, but almost every team (save a few expansion clubs) has had at least one man in place who had a decisive impact on the history of the franchise. The Orioles have at least three—Lee MacPhail, Harry Dalton, and Frank Cashen, who got the great Earl Weaver-era Orioles teams up, running, and maintained, and some would argue that you could throw in Paul Richards, Hank Peters, and Pat Gillick as well. The Yankees have had two Hall of Fame GMs in Ed Barrow and George Weiss, and Gene Michael did great things in rebuilding the team in the early 1990s. The Red Sox have had two as well. Dick O’Connell was instrumental in turning that team around after years of neglect, and Theo Epstein helped build the team that ended the long wait from 1918.

I could keep going, but let’s do this as a table, picking just one exec for each team:



New York AL

Tampa Bay


Harry Dalton

Dick O’Connell

Ed Barrow

Andrew Friedman

Pat Gillick

Chicago AL



Kansas City


Ken Williams

Bill Veeck

Jim Campbell

Joe Burke

Andy MacPhail

Los Angeles AL





Bill Stoneman

Sandy Alderson

Pat Gillick

Still Open?





New York NL



John Schuerholz

Dave Dombrowski

Frank Cashen

Paul Owens

Still Open?


Chicago NL





St. Louis

Still Open?

Bob Howsam

Gerry Hunsicker

Harry Dalton

Joe Brown

Branch Rickey



Los Angeles NL

San Diego

San Francisco

Still Open?

Dan O’Dowd

Branch Rickey

Kevin Towers

Brian Sabean


You can argue with some of these selections. Perhaps Stick Michael should be listed under the Yankees given Barrow’s racism and resistance to the farm system. Some might displace Branch Rickey with the Cardinals (Bing Devine) or Whitey Herzog and the Dodgers (Buzzie Bavasi). Perhaps I’ve given Bill Veeck too much credit for the 1948 Indians and John Hart not enough for the team’s rebirth in the 1990s.

These are useful and entertaining discussions to have, but the very fact that you can have them underscores the point about the Cubs—the only real discussion you can have is who doesn’t belong in that box post-Selee, who became extinct, along with Cubs champions, over 100 years ago. You could nominate William Veeck, Bill’s dad, who put together some good very teams and brought Joe McCarthy to the majors, but like Green he failed to win the ultimate prize, dying in office with his job unfinished.

The men who came later, William Walker, Boots Weber, Jim Gallagher, Wid Matthews (seven years), John Holland (15 years), Bob Kennedy, Ed Lynch, and the rest have failed to leave a major mark on the franchise (Matthews deserves slight credit for bringing integration to the Cubs so belatedly), at least not in a positive way. Matthews once explained his approach to scouting this way: “When I shake hands with a boy and he has a good grip, that’s one of the essentials. Then I pat him on the shoulder to see how muscular he is.” Moneyball it wasn’t. No wonder Rickey was moved to observe, “There is artistry in ineptitude, too, you know.”

This is the legacy that Hendry, now in his tenth year in office, needs to shake off if he is going to fill in that picture frame. He has 2008’s 97-win team to his credit, but that outfit crashed out of the first round of the playoffs in three games. Since then, the Cubs have won 83 and 75 games, and this year’s assemblage would seem to lack the offensive depth to change much with regard to that trend. He is now the longest-serving GM in team history after Holland, and his record is no less mixed than that of the man who masterminded both the 103-loss teams of 1963 and 1966 and the 92-win near-miss team of 1969.

Despite changing ownership over the years, the Cubs have apparently never been run with the slightest sense of urgency. Rather than look at specific deals or drafts, this lack of dedication would seem to be the real motivator of the championship drought. Hendry’s full-season teams have an average record of 83-79 and the ballpark sells out. That’s nice, but it hardly constitutes evidence of a plan. How many chances should a GM, particularly one in a major market, get? Where is the evidence of a consistent, thought-based approach?

I’m not suggesting Hendry should be replaced, or will be—owner Tom Ricketts has spoken highly of the man—but the bulk of his career with the Cubs is likely already behind him and the frame remains unfilled. Every team has a special GM, every team but the Cubs. Someday, they may even get around to hiring one.

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Is there a causation -correlation issue here? Is the reason there is no iconic GM or owner a direct result of futility rather than the other way around. If the Cubs could have won it in 1984 or 2003, would this article still have been written?

I think the picture frame will be filled when the Cubs win a world series.
No Buck Showalter for the Diamondbacks? or was he not GM during their pre-playing days?
Showalter was the field manager, not the GM
I stand corrected, but remember him being hired as a team architect during the two-year ramp up to their debut
So what's your take? How are they going to do? I have them predicted at 5th in the division, and have angered a Cubs fan cousin of mine in the process.
Of all the major sports franchises in Chicago, only the Bulls, and White Sox(regardless of ownership, though Reinsdorf is obviously the best example) have shown a propensity to want to win. The Cubs, Bears, and Blackhawks, appear to only have wanted to make money, by putting fannies in seats. Because of "the shrine", and the "lovable losers" tag, fannies in seats has never been a problem for the Cubs. The Bears, and most recently the Blackhawks, found that a few years of empty seats produces incentive to attempt to better the team. Although, there's no evidence that would have happened to the 'Hawks, if "Dollar Bill" Wirtz had not passed away.

BTW, Texas' Jon Daniels, could very well be the "pathfinder" for the Rangers. Very sharp young GM, who should net a WS title, or two, during his tenure.
Can you quantify this? What exactly have the Sox done that shows they "want" to win, that differentiates them from the Cubs?
The GM that figures out that playing in wrigley field and taking walks go hand in hand with winning baseball probably fills the frame. That won't be the current GM.

1984 and 2008 are the only years in my lifetime that the Cubs led the NL in runs. They are also the only years they led the NL in walks. This team is years away from contending again. Castro and Colvin come through the same system that produces hitter after hitter that can't take a walk. And pitcher after pitcher that issues free passes like krispy kreme dishes donuts.

It's a systemic problem.

I disagree with the contention that there hasn't been an iconic owner of the Cubs. There are two to choose from: William Wrigley, the owner in the days when the Cubs regularly contended and played in the World Series numerous times back in the early 20th century, and Phillip K Wrigley, the son of William and the one whose general disinterest in the team--and, notoriously, his idea for the "college of coaches"--held the Cubs back for a long, long time. The Cubs, as I recall, were one of the last teams to actually have what we would consider a modern farm system with affiliated minor league teams.

If the criteria to have an "iconic" general manager is that you win the World Series, then I suppose no, the Cubs really have no such GM in their history (or at least, no such GM that would be relevant to fans today in any way--sorry, GM from 1908). Jim Hendry, however, has presided over three playoff teams as GM, a better record than many others could claim in the same span of time. Personally, I'm happy Hendry's average team record is 83-75. Maybe that's the Cubs fan in me--content with mediocrity--but considering the ups and downs teams can have, only the elite are going to have a record much better than .500, and obviously the Cubs are not elite.

I do agree that Hendry hasn't given us an Epiphany, like Alderson and sabermetrics or Rickey and, uh, farm systems, but that's OK with me. Consider that Hendry is surely one of the longest-tenured GMs the Cubs have ever had.

Consider this: remember, you Cubs fans from the '70s, '80s, and '90s, every year the newspapers would write about the hole at third base: that no one had ever come close to stablizing the position since Ron Santo was traded to the White Sox. Not long after Hendry came along, he flipped Bobby Hill for Aramis Ramirez, and all those stories in March and April--they all went away. I like Hendry for getting the Cubs to the playoffs the times he has, although the team has done him no favors in their early exits the last few times; I like him for his winning record overall. But I think what makes him iconic, to me, is he ended the damned controversy over 3B. Pencil him into that table up there.
"primitiveness conditioning" = EPIC FAIL. I volunteer to proof the articles for you guys.
"Fail" is not a noun. Clean your own house first.
More generally, should we see the occasional typo, would you prefer that we comment below the article, send e-mail somewhere, or just ignore it?
The Cubs have the good fortune of playing in one of the most beautiful ballparks ever built, while also having the marketing might that comes with being televised nationally on cable superstation WGN. These factors virtually guarantee sellouts and advertising revenue whether they win 95 games or lose 95 games. Thus, their good fortune becomes a curse in that it removes much of the incentive for management to build a good organization. The bottom line is this organization needs to be entirely reconstructed, from ownership down, for the Cubs to win a World Series.
WGN stopped showing most Cubs night games after they purchases a large stake of the WB network. They needed the Chicago market to boost the ratings. That is how many people were stuck with The Jamie Kennedy Xperiment instead of baseball.

Now they show many games on the Comcast Sports Network. Thank goodness for MLB.TV, blackout dates notwithstanding.
Veeck did die with the job unfinished, but he built a great team in the 1930s that won 4 pennants in ten years. The Cubs just had the bad misfortune to run in to some of the greatest teams of all time in three of the four WS they played in (1929 Athletics,'32 and '38 Yankees) and the other one they just lost to a very good Tigers team. I think Veeck is the iconic GM you are looking for.

The issue with the Cubs has always been ownership, at least since William Wrigley died. His son PK wasn't really interested in winning pennants, but rather turning the Cubs and Wrigley Field into a shrine for his father. If you read much about PK Wrigley, you know the guy was an odd duck.

The Tribune was a lot better, but they lacked patience and much understanding of baseball. Until they hired Andy MacPhail and let him run things, they never had a baseball guy in charge. MacPhail had some success, but he could never get out of the mindset that won him two titles in Minnesota and didn't understand that couldn't be replicated in Chicago.

Hendry has been sacrificing the future for years now in an attempt to save his job. It almost worked in 2007 and 2008 (well, it did save his job) but he completely lacks any long term plan to build around. He's just trying to make it to next season, as the Garza trade shows.

Things seem to be better under the Ricketts and Crane Kenney, but only time will tell on that.
I agree with just about everything folks have written here - the ownership, the Wrigley/WGN money, the conservative leadership are all major factors in producing decades upon decades of bad teams.

But I think the fundamental problem for the Cubs, the root problem, is that the leadership has had no real drive to win since the Veeck days.

Organizational mandates come from the top, and generally speaking success can vary within a limited range defined by the leadership. The Twins under Pohlad hired some very good baseball people who did everything they could to draft excellent players - but ultimately Pohlad's complete disinterest in winning meant the Twins never made the in-season moves necessary to truly compete with the best AL teams. The one-and-done Marlins teams were defined by owners desperate to maximize earnings by putting superior efforts into single seasons with the full knowledge that the team's assets would be sold off in the subsequent offseasons. The Yankees and Henry Red Sox are obsessed with winning and put money and thought into each team; as a result, even though they occasionally drop to 3rd both teams are consistent winners.

I don't think this is a hard and fast rule - there have obviously been highly incompetent owners and managers committed to winning, and obviously any team that sneaks into the playoffs can win a short series or three. Even the Cubs may have been 2003 champions if a dropped fly ball or mishandled play at short had gone differently.

Ulimately though, the problem with the Cubs is that nobody at the top really cares. PK never really did, and lord knows the Trib's list of priorities had a lot of items on it preceding winning the World Series. Even Hendry, mixed bag though he is, seems to have been given a mandate: spend money to be successful enough to convince fans the Cubs are really trying and stay in the hunt deep enough into the season that we rake in the big bucks. Is there any wonder the team was late to integrate, late to integrate statistics, late to innovate in nearly every single way?

Obviously it is too soon to know how the Ricketts family will do, but I am not at all encouraged by the fact that the Cubs have seemingly 25 different Bud Selig-approved siblings each taking over a different role in the organization. Surely they can't all be right for their jobs, and even worse you have to wonder if any new baseball owner who can be approved by MLB's sachems isn't first and foremost interested in making money. After all, following an incredibly expensive and hugely disappointing season in the midst of an epic state budget crunch the Ricketts family's clear #1 goal is...getting state money to improve what is already one of the biggest draws in sports.

Wow, this turned out to be long...
The Twins won two World Series titles under Pohlad's ownership.
True, and maybe I should have mentioned that. But times changed and he didn't - he came in and saved the Twins and was great through 1991, but he began to run the team with profit first and foremost in mind and in many ways prevented them from competing with the big boys throughout the last decade - never mind the rest of the 90s. It's been 20 years since they last won.
JoshT has me convinced. "Mr. Goldman, tear down this chart!" And enter Veeck into it for the Cubs.
To Wrigleyviller: The Twins were cheap in the 90's and into the beginnings of the last decade, but times have changed. Rick Reed, Shannon Stewart, Orlando Cabrera, Matt Capps, etc. are examples of them making moves and adding salary during the season in an attempt to make a run. And the opening day payroll has increased from 15 million to 97 million in the last ten years. Please just let the stereotype die.
Did I actually read an endorsement for Crane Kenney in these comments?