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.