I’m going to try something new here and do a double-book review. (Mostly because I’m behind, but also because of a great theme that connects two very different books that I read back-to-back.)

At one point or another, probably in a dorm room well after midnight, I know that everyone has had a conversation that begins like this: “What would have happened if…?” Depending on your level of sobriety, that conversation could have been about whether you would have met the girl you just flipped for or about whether an entire social revolution wouldn’t have happened but for the music of The Beatles. Nevertheless, these kinds of conversations are fantastic, allowing us to root through our personal lives and our perspectives on the world around us, and to throw in a dash of creativity to spice things up.

Political types love this kind of conversation. What would have happened if the guard at the Ford Theatre hadn’t stepped away in 1865? Or what would have happened if the Watergate burglars hadn’t been sloppy and gotten caught? And sports aficionados could talk all night with random scenarios that involve just milliseconds or inches.

Jeff Greenfield’s “Then Everything Changed” takes the political approach and alters three important political events. Philip Roth’s “The Plot Against America” also goes for the political, but he writes an entirely different book that focuses more on a personal struggle against the backdrop of a completely different U.S. history. Both of these books are really fantasy books, but not the kind with unicorns and dragons. They instead ask us to envision imaginary worlds that are somewhat plausible.

Let’s start with Greenfield. I had more fun reading this book than any in months or years. Greenfield is a witty and sly writer who is far more than a commentator on CNN—he spent his early years writing speeches for Bobby Kennedy. Greenfield peppers the book with “inside jokes” that are recognizable to those who follow politics closely. As a first-person witness to many of the most important political events of the most recent 50 years, Greenfield is well qualified to don his speculation sunglasses and let ‘em rip. His first premise: John Kennedy was instead killed post-election and pre-inauguration when a deranged man blew him up with seven sticks of dynamite. Preposterous? Nope. This was an actual event—the bomber was in front of Kennedy’s house and got cold feet. He was caught four days later. Book one of “Then Everything Changed” imagines Lyndon Johnson as President through an early constitutional crisis, the civil rights movement, and the Cuban Missile Crisis.

Book two posits that Sirhan Sirhan misses Bobby Kennedy (with another strange but true twist of fate) and Bobby ends up as President instead of Nixon. His administration ends the Vietnam War and the book goes on to describe a scenario with a Kennedy aide involved in a Watergate-like crime that the press ignores. Greenfield does know his politics! The third book imagines that Gerald Ford did beat Carter (instead of digging in as Ford actually did, Greenfield’s fantasy Ford corrects his debate mistake and maintains momentum to victory). A one term Presidency for Ford gives way to the candidate of change, an Obama-like character—Gary Hart. (This book ended with my favorite of the inside jokes, which involves Hillary Clinton and the air traffic controllers strike. Read it.)

Greenfield has the chops to do this kind of book. He’s smart, and he researched this book like it was non-fiction. Though he runs dangerously close to the border of Corny-town at times (a dramatic death in the situation room), there are some real political learnings to be gained from this book. It is riveting to imagine Gary Hart’s presidential campaign and it is not far-fetched to think it would have looked a lot like Obama’s. How Lyndon would have governed through the Cuban Missile Crisis is equally fascinating. And reducing Reagan to a bit player angry about Bobby Kennedy stealing his lines is just funny.

(Book reading, as you know, can be a solitary hobby, and “Then Everything Changes” just accentuates that loneliness. Like with all of these parlor games, I wanted to have someone else to laugh and chat with about this book. If you choose to read it, call me, I’ll buy lunch.)

Philip Roth’s “A Plot Against America” was a gift from a now departed friend (she quit my company a month ago, leaving me nothing but a damn book), and it was this book that redeemed a long weekend of frustrating books. (See entries on “To Kill an Irishman” and “The Triumph of the City.”) “A Plot Against America” begins with this circumstance: Instead of winning a third term, Franklin Roosevelt is instead upset by Charles Lindburgh, an isolationist and anti-Semite, who leads the country down a dangerous path that bears a resemblance to early Nazi Germany.

Once you get past the “speculative” portion of this novel, you find not a parlor game, but a beautifully written portrait of a young boy navigating a world he doesn’t understand and that is changing around him. But that boy could have easily been any man—scared and confused at a world run off the rails. Roth’s unfamiliar America is a warning flag about what happens when government is led by those with an ill-informed and a dangerous worldview. (And it’s hard to ignore the fact that this book was published in 2004.) Roth, in a New York Times essay, cautions against drawing too many parallels, but they are indeed clearly present.

Also, as a fan of Michael Chabon’s writing, I couldn’t help but see some similarities in style and the issues each chose to address. While I prefer Chabon’s “Kavalier and Clay” to this, (indeed I prefer “Kavalier and Clay” to hundreds of other books) I think the triumph for Roth is that he balanced the intrigue of plausible historical fantasy with a strong emotional connection to the characters.

The difference between Roth and Greenberg is micro and macro. Roth’s book is ultimately about the life of a Jewish family in America had Roosevelt lost to Lindbergh. Greenberg’s is about how the American political experience would have been experienced with just a few tweaks to crucial moments in time.

Here I go again, running long on this blog. Let me end with this: a conversation starter, if you will. Books like these are centered around events that immediately and publicly changed history (an early Kennedy assassination, a Lindbergh victory), but our personal lives are often changed considerably by events that take more time to understand, and when understood, they don’t often wind up in the newspaper. For instance, it’s hard to imagine my life had a certain Xavier student not called me looking for her summer internship. So the question for tonight’s dorm room conversation is, what one moment would have changed your life?

Thanks for reading.