We continue our backward countdown of the teams that have gone longest without winning a World Series. In this installment: the worst of the original franchises.

Pittsburgh Pirates (1979)
Years since last championship: 31
Reason for gap: The 1979 team wasn’t built to last, with a fascinating mix of veterans who were just about done due to age or injury (like Willie Stargell, Rennie Stennett, Bill Robinson), and some players still in their prime who didn’t have much sensitivity to conditioning, like Bill Madlock, Dave Parker, and Lee Lacy. The starting rotation wasn’t deep, and while the bullpen was very good, it was also old. Under manager Chuck Tanner, the club did manage to rebuild the pitching staff for a time, but it was very slow to react to roster and clubhouse problems. A decade later, with the blossoming of Barry Bonds, Bobby Bonilla, Andy Van Slyke, and Doug Drabek, the Pirates enjoyed a brief return to the postseason, but once those players left or declined, the organization had nowhere to turn as the franchise experienced a financial decline that mirrored that of Pittsburgh itself.

Since the stars of the early '90s departed, the Pirates have only once ranked as high as 11th in the league in player payroll. Good players the organization did manage to acquire or develop were inevitably traded for more young players in a merry-go-round that quickly lost its purpose—if you’re never going to stop and consolidate then the team is never going to improve, but will function only to spin off player after player in an ever-widening cycle of diminishing returns. Thus did Jason Schmidt, Jason Bay, Aramis Ramirez, Brian Giles, and others get scattered across the leagues. Simultaneously, the Pirates followed the Commissioner’s line on the draft, rarely selecting the best talent available. The few times the organization chose to spend money on veterans, it made disastrous choices such as shortstop Pat Meares or outfielder Derek “Operation Shutdown” Bell. The Pirates may have lacked capital, but far more damaging was the team’s complete lack of leadership and vision.
President the last time they won: James Earl Carter.
Talk around the water-cooler: Three Mile Island; SALT II; OPEC raising prices and gas rationing; the taking of hostages at the U.S. embassy in Iran, the bailout of Chrysler, which posted over $1 billion in losses.
Top of the Charts When They Won: "Don’t Stop ‘Til You Get Enough" by Michael Jackson.
Closest They’ve Come Since: The Pirates coughed out just short of the World Series each year from 1990 to 1992, losing the NLCS in each year by seven, seven, and six games, respectively.
Chances of Winning This Year: The overall talent level is up and should continue to improve with Pedro Alvarez on the way, but the pitchers who are going to make the team relevant don’t appear to have joined the organization. The Pirates have had a very poor touch with pitchers in the first round of the draft, in part because of an aversion to paying out bonus money. Who they take at second overall this June will provide a big hint as to whether this is going to change, although last June’s overdraft of Tony Sanchez with the fourth overall pick was not a good sign.

San Francisco Giants (1954)
Years since last championship: 56
Reason for gap: Though the Giants’ long drought is no secret, it’s still somehow shocking to see the team so far down this list given its status as one of the National League’a great franchises. This is a franchise that has 17 modern pennants and five championships, the team of John McGraw, Christy Mathewson, Carl Hubbell, and Willie Mays. And yet, since they relocated to the West Coast, they haven’t been able to raise another flag. This is especially odd because the Giants have often had the talent to compete, have often had the financial support necessary, and have had the opportunity to win. Some aspects of the long slump are just a matter of bad luck, of not being able to win a key game in a postseason series. As Charles Schulz’s outraged response, a slightly different swing by Willie McCovey and we might not even be talking about more than a half-century without a Giants championship.

Notwithstanding the post-Bonds years, when Brian Sabean’s efforts to rebuild the team have been hamstrung by what must be an organizational edict not to sign any bats, it is tempting to say that, if we want to look for a global cause of over 50 years of frustration that overrides the transient needs of each separate Giants edition, it goes back a phrase used above: "since they relocated." What the heck was Horace Stoneham thinking when he followed the Dodgers out of town? Though he had supposedly already decided to depart (to Minnesota) when Walter O’Malley put visions of California in his head, spooked by declining attendance in the wake of the ’54 championship, had he remained, he would have had the whole of the National League market in New York City to himself. The short-term future may have been dark, but everything that accrued to the Mets in future years would have been his. After the early years in San Fran, Candlestick Park was generally a poor draw, and this undoubtedly handicapped the club’s efforts through the construction of AT&T Park.
President the last time they won: Dwight David Eisenhower, saying much too little about Joe McCarthy.
Talk around the water-cooler: The Army-McCarthy hearings; the fall of Dien Bien Phu; Brown vs. Board of Ed; J. Robert Oppenheimer’s security clearance; that loud "Rock and Roll" the kids are listening to.
Top of the Charts When They Won: "Hey There" by Rosemary Clooney. When she says, "Are you talking to me? " I thought it was Robert DeNiro on estrogen.
Closest They’ve Come Since: The Giants have reached the World Series three times since they upset the Indians in 1954. They dropped the 1962 and 2002 Series in seven games, while they were swept in 1989 by the Oakland A’s.
Chances of Winning This Year: Once again, the offense is unlikely to support Tim Lincecum and Matt Cain, but if they somehow slip into the postseason, they might be able to ride those pitchers to win it all. It’s asking for two long-shot bets to pay off in one season. 

Cleveland Indians (1948)
Years since last championship: 62
Reason for gap: Whole books have been written about the Indians' dead period. You can blame Hank Greenberg, Frank Lane, Gabe Paul, or any of the other general managers who failed to restart what had been a very successful club throughout the 1950s (.588 winning percentage from 1950-59) if you like, and as we shall see they surely contributed, but the real culprits were a succession of underfinanced owners who were incapable of giving the club the support it needed to retain its good players and rebuild through scouting and player development. Major League wasn't a comedy, it was a documentary. The club compounded its problems by being one of the most inept drafting teams into the 1980s. The Indians weren't able to pull anything approaching a star out of the first round of the draft from 1965 until… Greg Swindell in 1986? Charles Nagy in 1988? Manny Ramirez in 1991? Let's call it Albert Belle in the second round in 1987. Even when the Indians stumbled on a good player in later rounds, like Dennis Eckersley (third round, 1972) or Von Hayes (seventh round, 1979) or even Chris Chambliss (their first-round pick in the 1970 January draft), they failed to hold onto them. In dealing players like Eckersley, Chambliss, Luis Tiant, Dick Tidrow, and Graig Nettles, the Indians single-handedly made possible the YankeesRed Sox rivalry of the 1970s. The Indians rarely received anything like equal value in these deals, and failed to capitalize when they did, holding onto the player for a few years before dealing him off to another contender. In the 1990s, the Indians, reinvigorated by Jacobs Field and a shockingly successful player development operation, finally began fielding teams worthy of their history, but couldn't convert any of seven post-season appearances before that particular aggregation had run its course.
President the last time they won: Harry S Truman, on the way to winning an improbable re-election campaign.
Talk around the water-cooler: The Marshall Plan; the creation of Israel and the United States’ recognition thereof; fun with HUAC; strike by coal miners; high inflation; Alger Hiss vs. Whitaker Chambers; the integration of the armed forces; the Kinsey Report; Milton Berle’s "Texaco Star Theatre" TV show. It was a very busy year.
Top of the Charts When They Won: "A Tree in the Meadow" by Margaret Whiting.
Closest They’ve Come Since: The Indians lost the 1995 and 1997 World Series, the latter in the 11th inning of the seventh game.
Chances of Winning This Year: The pitching just isn't there, and the offense arguably isn't either.

Chicago Cubs (1908)
Years since last championship: 102
Reason for gap: There is no easy way to sum up over a century of futility in a single paragraph, no matter how overstuffed. The gentlest thing to say is that the Cubs have been run whimsically. They have had fishmongers as team presidents. They have had a "college of coaches" instead of a manager. This merely succeeded in multiplying what has been a long history of terrible taste in managers, from a past-it Leo Durocher to Don Zimmer to Don Baylor to Dusty Baker. Baker, who made a point of running the patient Mark Bellhorn out of town, is emblematic of a strange inability on the part of this franchise to draw walks. When you play in a hitter's park and don't make a priority of reaching base, you've put yourself at a tremendous disadvantage; sure, you're going to hit a home run every game, but it's likely to be a solo shot, while your more patient opponent is more likely to trump you with an Earl Weaver-style three-run blast. In the modern history of the Cubs, only nine batters have drawn 100 walks in a season, and they've had just four 100-walk seasons since 1930. In this, they have failed to support some fairly solid pitching staffs. Broadly speaking, in their modern history the Cubs have had just under a third of their single-season pitching staffs have been substantially below average, but roughly half of their single-season offenses have been below average.
President the last time they won: Theodore Roosevelt, sending the Great White Fleet around the world.
Talk around the water-cooler: The presidential election, with Republican William Howard Taft running against William Jennings Bryan; the acquittal of Harry Thaw in the murder of Stanford White by reason of the novel insanity defense; crazy-high unemployment (estimated at eight percent, though statistics weren’t reliable); the Model T Ford goes on sale, bringing automotive transport and air pollution to the masses.
Top of the Charts When They Won: There were no charts as broadcast media had yet to be invented, but popular recorded or performed songs included "Shine On, Harvest Moon," "All She Gets from the Iceman is Ice", and the brand-new composition "Take Me Out to the Ballgame."
Closest They’ve Come Since: The Cubs were blown out in the seventh game of the 1945 World Series. They haven't been back to the big dance since. In sporadic post-season appearances since then, they've lost the NLDS and NLCS three times each.
Chances of Winning This Year: This aging unit has decent pitching but is undermanned offensively. They could win the NL Central if the Cardinals slip, but going all the way is a lot to ask.   

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'Charles Schultz's' and 'Outraged Response' are both links to the same site. Accident?
Yes. It was meant to be two different strips. The second of them can be found here:

The Pirates lost to the Braves in 7 games in 1992, not 6.

And Cleveland didn't exactly hand a primo condition Luis Tiant over to the Red Sox. He lost 100 strikeouts in 1969 that he'd had in 1968 pitching similar innings totals. The Twins didn't find much use for him either and he didn't pitch very well for the Red Sox in 1971. It wasn't till part way through 1972 that he was El Tiante, again. The Indians deserve a pass.
Cubs: "There were no charts as broadcast media had yet to be invented"
This is sad and I am not even a Cubs fan.
Four 100-walk seasons in 80 years? How is that even possible? I note that there have been on the order of 440 100-walk seasons since 1930, and roughly 1760 team-years in the time -- meaning each team should average about one 100-walk season every four years (not twenty).

Why no analysis of the Padres, Astros, Rangers, or Mariners, who should all slot in between the Pirates and Giants? (Part IV?)
I'm pretty sure, in an earlier article of this series, he said he'd treat those never-won, expansion teams separately.
That's my intention. Just trying to keep these entries to a manageable length.
I loved this passage:

"Good players the organization did manage to acquire or develop were inevitably traded for more young players in a merry-go-round that quickly lost its purpose—if you’re never going to stop and consolidate then the team is never going to improve, but will function only to spin off player after player in an ever-widening cycle of diminishing returns"

Too many MLB teams, even well-run ones, having been doing this far too long.

I've been trying to articulate this thought for a long time, and then, BAM, you wrote it perfectly.
I really enjoyed this. It's a great idea to apply everything we know today about statistics, drafts, player development, etc., to discussions about how teams did things years and years ago, back before the flow of information became so unrestricted. Sometimes it seems like there are a lot of fascinating historical narratives about older teams, and a lot of sharp current-day analysis, but the two don't often combine.