1. Don Draper = St. Louis Cardinals
Like Don Draper, there is something clean cut and All-American about the Cardinals. They’re not everyone’s favorite team, but baseball fans generally respect the organization for their ability to win, both now and previously.
Both Draper and the Cardinals seem to abide by a code of ethics. For all his womanizing and secrets, Don is not judgmental toward his colleagues or people in general. And during his tenure as St. Louis’ manager, Tony La Russa always seemed to act with the sanctity of the game fully in mind in addition to winning ball games.
(This is also a default pick in acknowledgement of Jon Hamm’s real-life fandom of the Cardinals.)
2. Peggy Olsen = Tampa Bay Rays
Hasn’t it been heartwarming to watch both of their ascents? Peggy used to be just another secretary and was forced to endure snide comments about her weight. The Rays used to be a perennial punching bag, a habitual cellar dweller in the American League East.
Fast forward: Peggy becomes the first female copywriter at Sterling Cooper since World War II, and when she makes the move to SCDP she is one of the few people Don trusts. And those plucky Rays are now contending for the AL East title on a regular basis. Their combination of youth and savvy (two traits they share with Peggy) assures that they’ll be doing so for many years to come.
3. Pete Campbell = Boston Red Sox
Both are bestowed with upbringings that seemingly guarantee success. Pete comes from the wealthy Dyckman family, while the Red Sox have one of the strongest heritages in the majors. At times Pete and the Red Sox have made the most of these gifts, with Pete making partner at SCDP and Boston winning two World Series titles in the past decade.
Yet both have their share of mishaps they can’t blame on anyone but themselves. No one forced Pete to commit infidelity or reveal to his mother that his late father had squandered the family’s life savings. No one forced the Red Sox into foolishly signing the likes of Carl Crawford, J.D. Drew or Julio Lugo.
There’s stubbornness to each, a belief that whatever they do should work because “I’m Pete Campbell” or “We’re the Red Sox.” For all their successes, they can be real pains in the ass.
4. Roger Sterling = New York Yankees
They were seemingly born into positions of power and authority over their respective domains. They’re also incredibly smug and self-serving, but their track records of doing business justify that persona.
They both endure enough slip ups where you see that they’re fallible. How could Roger lose Lucky Strike when it was the only client he was responsible for? How did the Yankees blow a 3–0 lead in the 2004 American League Championship Series? Whether you’re for or against them, you admit that they make for some great drama.
5. Joan Holloway = Miami Marlins
The former is the bombshell of Mad Men. The latter is the new bombshell of baseball entering the 2012 season.
Each season of Mad Men has featured many beauties, and Joan blows each one of them out of the water with her “talent.” Speaking of talent, it’s tough to think of another team in the majors as stacked as this year’s Marlins. Even before it added Jose Reyes, Mark Buehrle and Heath Bell in the offseason, Miami still had impressive young players like Josh Johnson and Giancarlo Stanton.
And let’s face it. If any major league city is going to have a steady supply of women as naturally curvaceous as Joan Holloway, it’s Miami.
6. Betty Draper = Chicago Cubs
There’s stunning beauty to each. Babs is the epitome of the doting Stepford wife from the 1960’s, with flowing blonde hair and stunning blue eyes. To many baseball fans, nothing is more beautiful than day baseball at Wrigley Field with its ivy-covered walls, old-fashioned centerfield and plentiful cheap beer.
That beauty, however, masks deep dysfunction. Yes, a good deal of Betty’s unhappiness can be blamed on Don’s failures as a husband, but an argument can be made that her emotional immaturity is wholly separate from that. She does not get along with her daughter Sally, and her hurried marriage to Henry Francis came across as incredibly selfish.
The Cubs, meanwhile, are now 103 seasons and counting without a World Series title. Going to games at Wrigley is still a treat, but new president Theo Epstein will have his hands full trying to get the organization back on the winning track.
7. Ken Cosgrove = Los Angeles Angels of Anaheim
One is the most perpetually happy man on Mad Men. (The only time I recall seeing Ken not smile was when he learned of Lucky Strike’s defection to BBDO.) The other is the most perpetually sunny franchise in baseball.
Since Season One, Ken has seemed to genuinely enjoy his life and work. Heck, he’s a published writer in The Atlantic Monthly and doesn’t make a big deal out of it. And while he does his share of drinking, gossiping and flirting at the office, Ken is a competent executive and creative thinker. People seem to really like him (unless you’re Pete Campbell).
Angels owner Arte Moreno is adamant about doing anything and everything he can to make the team successful and the fans satisfied. Whether its cutting ticket and beer prices, shelling out for the most talented free agents or increasing the team’s television revenue, Moreno and the Angels do everything with happiness in mind.
8. Duck Phillips = New York Mets
Remember how much potential Duck showed when he arrived at Sterling Cooper? He was ready to broaden the client base and arranged the merger with Putnam, Powell & Lowe. Remember how the Mets seemed poised to bring the World Series trophy back to Queens? They had great young talent and a general manager, Omar Minaya, who could do no wrong.
That was a long time ago. Or at least it feels like it.
These days Duck is stuck pining for Peggy—both as a lover and a business partner—and attempting to defecate on what he thinks is Don’s chair (when in fact it’s Roger’s). As for the Mets? When you’ve been defrauded through a Ponzi scheme and your up-and-coming first baseman comes down with valley fever, you know you’re having a rough time.