Best of Chicago Sports Stuff & Strat-O-Matic: 1969 Cubs vs. 2016 Cubs
Strat-O-Matic celebration week continues with a simulated cross-generational classic.
WHEN WE WERE KIDS, we all had a favorite player.
Our favorite players, however, weren’t necessarily good.
To wit: My Cubs guy in the 1970s was this shrimpy fastballer by the name of Bill Caudill. (If you know who he is, your last name is probably Caudill.)
Baseball Reference lists Caudill at 6’1”, 190, but I call bullshit on that one — dude was, at most, 5’7”, 154.
I dug Caudill because even though he was a shrimp, he boasted a 90-plus-MPH heater, and back in the stone ages, 90-plus wasn’t a regular thing.
In his three years with the Cubs, Caudill and his fastball racked up a record of 6-18, and while he K’d up 261 opponents, he walked 131. What with his combination of speed and wildness, he was Nolan Ryan Lite. Very Lite.
Some of my favorite players, however, were quite good, one of them being Cubbies right hander Ken Holtzman.
Young baseball fans of my vintage weren’t as sophisticated as today’s newbies. We didn’t know from WHIP, or slash lines, or exit velocities. For us, it was batting average, hits, runs, RBIs, wins, losses, saves, ERA, and that’s it.
But subconsciously, we did know about tribalism. Holtzman was Jewish. I was Jewish (barely). And that was enough for me. Kenny was my guy. (Or at least one of my guys. Because, Ernie Banks.) Unlike Caudill, two-time All-Star Holtzman was a beast, finishing his career with a record of 174-150 and an ERA of 3.49.
In 1969, Holtzman was one of the anchors of a scary-good Cubs staff that featured Hall of Famer (and another Alan Goldsher favorite) Fergie Jenkins and cold-blooded reliever Phil Regan.
Now I wasn’t old enough to be cognizant of what was going on in the Major League, circa 1969 — my man-crush on Holtzman didn’t kick in until 1971 — but I’m enough of a baseball historian to know what happened to the ‘69 Cubbies. In a nutshell:
Began the season winning 11 of 12.
Stayed in first place from Opening Day until September 9.
On September 9, a black cat ran onto the Wrigley Field turf and dumped bad luck all over the dugout circle.
Went 8-16 in September, ultimately finishing a distant second behind the eventual champs, the New York “Miracle” Mets.
It took over four decades for the Cubs to shake the black cat jinx.
THE 2016 CHICAGO CUBS were cuddly af.
You’ve got the handsome MVP Kris Bryant. You’ve got the lovable first baseman Anthony Rizzo. You’ve got irreverent manager Joe Maddon. You’ve got four starters — Jon Lester, Jake Arrieta, Kyle Hendricks, and Jason Hammel — who won 15 or more games.
And you’ve got a World Series ring.
They finished the regular season with a record of 103-58-1, the fifth-best in franchise history. Conversely, the ‘69 Cubs went a respectable 92-70.
Despite the divide between the two teams — one got a ‘chip, one got a cat — they’re often mentioned in the same breath. One was the team that could. One was the team that did.
Which got me to wondering how they’d stack up against one another? Could manager Leo Durocher’s Sixty-Niners hang with Maddon and his champs?
I asked the fine folks at Strat-O-Matic to game out a best-of-seven series between the old-school Cubbies and the older-school Cubbies, and they did just that. The results were more-than-a-little surprising.
GAME ONE
My man Fergie Jenkins was en fuego, throwing 7.2 innings of seven-hit, one-run ball, racking up nine K’s along the way. Ron Santo drove in a pair of runs and, despite a fine outing from Jon Lester, the Sixty-Niners pulled out an eye-opening series-opening victory.
GAME TWO
For all practical purposes, this one was over in the first inning, when Billy Williams smacked a two-run dinger into the right field bleachers. Bill Hands went 8.2 innings before yielding to Phil Regan, who picked up his second consecutive save. Ben Zobrist’s two-run homer in the sixth wasn’t enough for the Sixteeners to take advantage of a vintage Kyle Hendricks performance.
GAME THREE
The wind at Wrigley Field was blowing out, which means bleacher balls galore. Bryant jacked a pair, while Rizzo, Zobrist, and Javier Baez each gave the Bleacher Bums a special parting gift. My fellow Jew Holtzman did a decent enough job before getting chased in the seventh inning. Despite a six-run eighth from the Sixty-Niners, the modern Cubs managed to take it across the finish line.
GAME FOUR
Durocher shortened the Sixty-Niners’ rotation, so Jenkins took the mound on just three days rest — and it didn’t end well, with the Canadian righty allowing an un-Fergie-like four runs in 4.2 innings. (His defense’s five errors sure didn’t help.) In a surprise start, John Lackey and his bullpen allowed five total hits, knotting up the series at two.
GAME FIVE
The future Cubbies took a series lead thanks to dominant mound work from Lester and his squad’s always-effective bullpen. Jim Hickman’s two solo homers weren’t enough to overcome Wilson Contreras’ pair of jacks, leaving the Sixteeners one win away from wrapping things up.
GAME SIX
This was the reverse image of game five, as the teams combined for 19 runs and 21 hits. Despite a furious five-run eighth inning rally, the Sixty-Niners couldn’t overcome their early four-run deficit. Naturally, Rizzo put it to bed, hauling in Hickman’s last-gasp pop-up.
STRAT-O-MATIC’S simulation tells us that the series’ MVP was, of all people, Albert Almora who, along with his .538 batting average, posted an home run, three ribbies, and four doubles. Brizzo (a.k.a., Bryant and Rizzo) combined for three homers and nine RBIs, while Zobrist managed a trio of dingers and seven hits of his own.
While the Sixteeners did damage to the Wrigley scoreboard, it was the fact that they kept Ernie Banks relatively under wraps — .273 average and just one home run — that ultimately proved they’re the tougher of the Chicago Cubs’ most iconic modern iterations.
(This article was originally published on January 24, 2025)