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The Bet: Why the A’s will win more games than the Padres in 2021

Whether winning or losing, the A’s are a reliable inspiration for eccentric bets.

Oakland Athletics v San Diego Padres Photo by Christian Petersen/Getty Images

Every year, I make a bet with a guy named Robby. He was born in Georgia and lives in San Diego so, naturally, he is a Boston Red Sox fan. (I just report the facts; I don’t explain them.) Despite his choice of teams, Robby is a dedicated baseball aficionado. He was once a scrappy second baseman for his Georgia high school team before a stint in the Middle East League as an Army Ranger.

Robby indulges me every season by fading me on some of my fanciful, eccentric bets. The stakes are always the same, a bottle of Jack Daniels. We are not wagering the rent or baby’s milk money here. Our gambles involve either the Red Sox, or the A’s, or both. This year’s bet involves the Athletics and the San Diego Padres.

This was the bet I offered Robby: In 2021, the broke-ass, cheapskate Oakland Athletics will win as many (or more) regular season games as the newly glamorous, high-powered, free-spending San Diego Padres. Being a Southern gentleman, Robby did not call me an idiot to my face but he did take the wager awfully fast.

What Robby doesn’t realize is, he is destined to lose his sippin’ whiskey wager. Why? I have an advantage — or, rather, he has a disadvantage. He follows the national baseball press, which means, effectively, he has no useful, accurate or insightful information about the A’s.

This offseason, the national story line about the A’s was dismal. The team lost eight free agents, including a front rank closer (Liam Hendriks) and an upper tier shortstop (Marcus Semien.) The A’s could purchase no replacements because they’re the A’s, no attendance, cheap owner, money tied up in land deals, yadda, yadda. Even worse, the club’s minor league farm had gone barren, featuring only two of the top 100 prospects on’s list. The fact that the Athletics had squeaked out the equivalent of 97 wins in each of the last three season didn’t even make a dent in the depressing narrative.

Ergo, the A’s are doomed in 2021.

In contrast, the Padres made plenty of offseason headlines, most of them related to money spent and high-profile trades made. The Friars traded for Mike Clevinger last summer, whose arm promptly fell off. But the irrepressible Padres then acquired Yu Darvish, Blake Snell and Joe Musgrove. They signed Korean wonder Ha-Seong Kim. They tipped Fernando Tatis, Jr. 300 gazillion dollars. And there you have the recipe for offseason plaudits: spend BIG, trade BIG.

How could the pathetic A’s compete with that? “No way in Hell,” according to everybody and his brother. But I am nothing if not a reasonable man. I have done extensive analysis of the betting proposition. So, here are eight reasons I will win the bet and Robby will lose. This is my story and I will stick with it until the whiskey runs out.

  1. Fernando Tatis, Jr. will strain a hammy dragging his wallet around the infield. $340 million in one dollar bills weighs 391,000 tons. (I looked it up.) Try legging out a double with that in your back pocket.
  2. Eric Hosmer. Any team that signs the fading Eric Hosmer to an eight-year, $144 million contract doesn’t deserve to win anything. The only way Hosmer creates value on his contract is by buying every Padres fan beer for the next 20 years.
  3. Manny Machado was a jerk in Baltimore. He may play for the Padres now but what he did to the A’s Josh Donaldson a century ago in Baltimore still counts against him.
  4. San Diego has too many pitchers. Yu Darvish, Blake Snell, Joe Musgrove, and Dinelson Lamet, c’mon, man! Chris Paddack, their premier pitcher last year, is now their No. 5 starter. Before he was physically restrained, A. J. Preller, San Diego’s President of Baseball Ops, actually tried to sign Hippocrates, hoping he could heal Mike Clevinger. The deal never happened because Hippocrates refused to play with Manny Machado, oath be damned.
  5. The (Not Even Close To) Los Angeles Angels. The Angels have two things going for them: Mike (Effin!) Trout and Arte Moreno’s bank account. Between 2011, the year Trout made his major league debut, and 2019, the last full season, the Angels won an average of 82 games per year. Last year, they only lost 36 games … because they only played 60 games … with Mike (Effin!) Trout! My point is, the Padres had better hope Fernando Tatis, Jr. is not the new Mike Trout or they are in trouble.
  6. San Diego has a better ballpark than the Athletics. Any team with a better ballpark than the A’s deserves to lose to the A’s, every time.
  7. The A’s never do what reasonable people expect. Based on their Spring Training performance, I reasonably concluded the A’s were destined for World Series immortality. So, they opened the season 0-6, outscored by 800 runs per game. (I may have lost count.) After the first week’s performance, I concluded the A’s would trade Matt Chapman, Matt Olson, and Matt Damon for two single-A players. But now, the A’s are winning. My point is …who knows?
  8. I am writing this story, not Robby.

So what will happen? Who will win the bet? At the moment I am writing, the A’s are struggling at 3-7; the Padres are 8-3. Robby is probably laughing right now, but I’ve got him right where I want him.

Case in point: At the time this was published, the A’s had improved to 9-7, with the Padres at 10-7. Maybe I should have asked for long odds.