Written by Andrew Clayman

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In his famous pitch to Kodak, the ever-charismatic Don Draper describes nostalgia as “a twinge in the heart, far more powerful than memory alone.” Well, not unlike a carousel projector, sports can help crystalize those otherwise distant recollections of the past, as well—giving us context and a “feel” for the way things were; even if we weren’t actually there ourselves. Case in point, have you ever been watching an episode of Mad Men and thought to yourself, “I wonder what the Cleveland Indians were up to at this exact moment in history?” If so, you’re way too involved with your baseball team… and this is the article for you!

The Cleveland Indians MAD MEN Timeline: 1960-1966

Beyond mere entertainment, a sports team is a collection of moments and characters that can eventually become useful mile-markers on the pothole-ridden roads of our memories. Len Barker brings hazy visions of 1981 into focus, while Jose Mesa’s shadow still lurks over 1997. If you lived through the 1960s, there are certainly dozens of examples of this phenomenon back then, too—be it the trade of Rocky Colavito or the strikeout exploits of “Sudden” Sam McDowell. For those of us who missed out on this almost obnoxiously pivotal decade, however, we’re left to live it out vicariously through the colorful cast of characters on Mad Men (or The Wonder Years, if you’re nostalgic for the ‘90s version of ‘60s nostalgia).  All we’re missing is a little baseball context to these retro adventures, and Lane Pryce’s ill-fated Mets pennant just isn’t sufficient.

So, without further ado, here is what your Cleveland Indians were doing while various memorable events were unfolding at Sterling Cooper Draper Pryce*.

*With the understanding that Mad Men is a fictional television show and—like nostalgia—only a loose, soap operatic approximation of the past.

WARNING: SPOILERS AHEAD

March 18, 1960
A young, naïve Peggy Olson arrives in the big city and becomes the new secretary at Sterling Cooper. Meanwhile, in Hollywood, Florida, the impressive Indians have stockpiled some ambitious youngsters of their own—Rocky Colavito (26), Herb Score (26), and newcomer Norm Cash (25) among them. Tragedy strikes on March 18, however, as 40 year-old pitcher Dixie Howell collapses and dies of a heart attack during running drills. Roger Sterling takes no notice.

April 12-18, 1960
Don Draper’s world is turned upside down when his profile in Advertising Age brings his long lost brother back into his life. Frank “Trader” Lane throws Tribe fans into a similar state of panic when he trades away Cash, Score, AND the beloved Colavito in three separate deals just days before Opening Day.

July 13, 1960
As JFK wins his party’s nomination and the former Dick Whitman dreams up campaign strategies for Dick Nixon, the Indians send pitcher Dick Stigman to the All-Star Game at Yankee Stadium. Vic Power, Harvey Kuenn, and Gary Bell also make the American League squad. Across town in Manhattan, Peggy is starting to look plump. And out in the burbs, Betty Draper is capping pigeons in the backyard.

September 2-5, 1960
The aimless Indians have swapped managers with the Tigers (goodbye Joe Gordon, hello Jimmy Dykes), and Don Draper is looking for a client to replace Dr. Scholl's. “The day you sign a client is the day you start losing them,” says Roger Sterling, right before taking Draper out for a night on the town to get over his sorrows. “When God closes a door, he opens a dress.” Over this same weekend, the Indians sweep four straight from the Royals and split a Labor Day double-dip with Detroit. Mudcat Grant strikes out 10 and Tito Francona homers in a losing effort in the matinee. But Woodie Held hits his fourth homer of the weekend and Barry Latman goes the distance in the nightcap. Sterling is so stunned that he has a heart attack of his own. He survives, but the Tribe does not—doomed to a final record of 76-78.

1961
Mad Men gives ’61 a miss entirely, leaving out the heroics of former Tribe prospects Norm Cash (.361) and Roger Maris (61 HR), as well as the slightly less noteworthy remaining Tribesman Willie Kirkland, who paces the club in homeruns and ribbies. Central Catholic grad Sam McDowell also makes his Major League debut—at just 18 years of age—tossing six shutout innings in a 3-2 Tribe loss on September 15. Cleveland finishes 78-83 for the season.

April 10, 1962
Harry Crane convinces wary clients to buy ad time during a controversial episode of the TV show The Defenders. Two nights after the show airs, the Indians blank the Red Sox in Boston on Opening Day, 4-0. Yet another Dick-- Dick Donovan—gets the complete-game win, while Woodie Held and John Romano star at the plate. Pete Campbell mourns the tragic loss of his dad, and perhaps more importantly, American Airlines as a client.

May 18, 1962
Comedian Jimmy Barrett gets punchy with Don for thumbing his wife Bobbie. Meanwhile, Dick Donovan is on fire! The Tribe blasts Detroit 9-2 to hold on to first place at 19-11 on the season. In the shellacking of Colavito, Cash & the Kitties, Donovan pitches another complete game to improve to 7-0 on the year. As if that weren’t enough, he also cracks TWO homeruns to help his own cause. Chuck Essegian and Willie Kirkland add bombs of their own and Tito Francona posts three hits, as the Tribe keeps rolling.

August 5, 1962
Joan is devastated by the death of Marilyn Monroe, Betty kicks Don out of the house, Freddy is pissing himself, and Peggy is rejecting Colin Hanks’ Catholic advances. Sadder still, the Indians’ season has taken a wrong turn. They drop both ends of a twin bill at home to Kansas City on August 5. Barry Latman takes it on the chin in the day game, 3-2, and Pedro Ramos takes the L in the nightcap, 5-2, in front of less than 9,000 at the old Stadium. At 53-55, the Tribe is now 13 games out of first.

Late September, 1962
Don goes to L.A., and the Indians dutifully follow suit. Maybe Mudcat Grant chatted with Don and Pete at the airport. We’ll never know (except that he didn’t cuz they are fictional!). In any case, the Tribe takes 2-of-3 against the Angels, and the star of the weekend is 24 year-old outfielder Walt Bond-- a September call-up who winds up mashing 6 homers, driving in 17, and hitting .380 in just 12 games. Bond looks like a future star, and when Dr. No opens in theaters a month later, his timing seems perfect. As it turns out, though, Walt Bond has already played his final game for the Indians. Cleveland finishes the season 80-82, sixth in the AL.

March 1963
Pete Campbell and Kenny Cosgrove are moving up in the world, both promoted to head of accounts. Meanwhile, the Tribe has its fourth manager in as many years, as Birdie Tebbetts takes the reins.

May 4, 1963
While Roger goes full minstrel at his “Derby Days Soiree,” Peggy and the creative underlings are back at the office getting stoned. “I’m Peggy Olson and I want to smoke some marijuana!” Back in the burbs, Betty is drinking and smoking through the final month of her pregnancy with baby Gene (whatever happened to that kid?). And out in Los Angeles, the Tribe shuts out the Angels behind nine sterling innings from the Mudcat.

July 3-4, 1963
A secretary on a tractor costs a snooty British fellow his foot. “And right when he got it in the door,” chimes Roger. Meanwhile, in a holiday double-header, the Tribe takes two from the Red Sox in Cleveland. In the first contest, light-hitting Indians shortstop Jerry Kindall ends a 14-inning marathon with an unlikely walkoff homer to secure a 4-3 win. After a brief breather, the teams take the field again, and Kindall homers again (as does John Romano), as Mudcat overcomes three hits from Yaz to get the win in a 7-5 Tribe triumph. The Indians are back to within 7.5 games of first place. They will never get any closer.

August 28, 1963
Don picks up Sally’s hot teacher and they listen to MLK’s “I Have a Dream” speech together. Naturally, the Indians are busy playing yet another double-header-- this time, a depressing sweep at the hands of the ChiSox, 8-3 and 3-1. Only 7,777 attend the nightcap in Cleveland, as the once mighty Dick Donovan suffers his 11th loss (despite homering for old time’s sake). The Tribe is on its way to another ho-hum 79-83 finish. In the months ahead, Betty will learn Don’s secret, JFK will be killed, and the new Sterling Cooper Draper Pryce agency will be born.

1964
The Mad Men universe skips over another entire year while the Tribe stumbles along its inescapable path of mediocrity. Not to be outdone by Roger Sterling, manager Birdie Tebbetts suffers a heart attack in Spring Training, returning in July merely to lead his team to another 79-83 finish.

January 20, 1965
Betty is now hitched to Henry Francis. Don has just learned that Anna Draper has cancer. Joan is looking to make a baby with her rapist husband. Lane is hooking up with Playboy bunnies. And Rocky Colavito is back in Cleveland! Unfortunately, the Indians have to send away Tommy John, Tommie Agee, and John Romano to reacquire The Rock, who’s hefty contract will pay him $55,000.

April  21, 1965
Don wins a Clio award, fails to acknowledge Peggy’s contributions (as usual), gets wasted for a weekend, and wakes up with a random dame who calls him Dick. In the Indians home opener, the prodigal son Colavito homers in a 6-5 Cleveland victory. Sonny Siebert gets the win when Daddy Wags Wagner hits his second homer of the game to lead off the bottom of the 10th inning.

May 25, 1965
Anna dies, Don and Peggy bond, and Sterling checks out Ali-Liston II. Down the road from SCDP in the Bronx, the Indians beat the scuffling Yankees 5-1 to move to 18-17 on the season. Fred Whitfield and Vic Davalillo homer off Jim Bouton. And Sonny Siebert and Sam McDowell (4 inning save out of the pen) combine to strikeout 12 and shutdown an aging Maris and Mantle.

August 15, 1965
Joan’s knocked up (it ain’t her husband’s), Roger is losing Lucky Strike, and Don’s making confessions to Dr. Faye. On August 15, he takes his daughter Sally to see the Beatles at Shea Stadium. While they’re there, the second-place Indians are hosting the surprising first-place Twins in a battle with actual pennant implications! As you would presume, it’s another doubleheader, with the day game featuring a fantastic pitching duel between Tribe ace Luis Tiant and his former teammate turned Minnesota hurler Mudcat Grant. The Twins take it 4-3. Later that evening, Cleveland bounces back with a 6-4 win, as Jack Kralick gets the win over another ex-Indian, Dick Stigman. Weirder still, the aforementioned banjo hitting Jerry Kindall—also now a Twin—homers yet again. But Rocky, Daddy Wags, and Max Alvis do the same for the Tribe, as they climb to within eight games of the Twinkies in front of 41,000 fans at Municipal Stadium. As is the pattern, though, they will never get any closer. Six weeks later, the Indians end the year 87-75, 15 games behind the pennant winning Twins.

May 1966
A lot can happen in an offseason. Ex actress/secretary Megan is the new Mrs. Draper, and Vernon Stauffer is the new owner of the Indians (for a cool $8 million). The month of May begins with Sam McDowell throwing his second consecutive one-hitter, and it ends with Megan seductively singing “Zou Bisou Bisou” to her uncomfortable birthday boy husband.

July 2, 1966
Fat Betty makes her world television debut, and Don and Harry hangout awkwardly backstage at a Rolling Stones show. The same night, the Indians beat the Angels 5-2 behind a complete game from Sonny Siebert. That’s four straight wins for Cleveland, as their 45-29 record has them in the thick of the hunt again. They will lose 11 of their next 12.

July 30, 1966
Don fixes the sink at Pete’s suburban dinner party, Lane watches England win the World Cup with some blowhards from Jaguar, and the Tribe’s Gary Bell is outdueled by the Angels’ Dean Chance 2-1 in Los Angeles, leaving the Indians 13.5 games out of first place.

August 25-28, 1966
Don leaves Megan at the Howard Johnsons in Plattsburgh, Roger trips balls with Jane, and little baby Albert Belle is born in Shreveport, Louisiana. Somewhere in that out-of-sequence narrative, the Indians are also swept three-straight in a weekend series with the Washington Senators. Stumbling down the stretch, Cleveland finishes 81-81, bringing the franchise’s total record during the Mad Men era to 560 wins, 565 losses—a model of bland consistency in a time of seismic shifts.