It has been a couple weeks since the Crosstown Centurion Field has been unveiled with the 16 best White Sox and 16 best Cubs teams of all time. Since Pat has broken down the Sox side of the bracket, it is my turn to do the same for the Cubs side. For those of you who may need a refresher or didn’t listen to the Shoeless Goat Podcast bracket reveal episode, the field is below.
As a reminder of the tournament format, each round will consist of best of 7 matchups, with each game being fully simulated. The series format will go 2-3-2 (in terms of home field), with the higher seed opening and closing the series at home. The lineups and batting orders will not change between games, but the starting pitcher will be changed to facilitate four man rotations.
Without further ado, here are my first round picks and general predictions for the the Cubs side of the Crosstown Centurion bracket. The first round features four match-ups between teams with at least 99 years between them (gaps of 110, 107, 102, 99 years), so we’re in for a wild ride.
1. 2016 (103-58) vs. 16. 1998 (90-73)
Cubs fans young and old will gladly tell you exactly where they were on the night of November 2, 2016. On a rainy night in Cleveland, the Chicago Cubs ended a 108-year World Series Championship drought in extras. They face off against arguably the most dangerous 16 seed sans UMBC in any bracket ever created. The 1998 Cubs featured a 66 home run-hitting (all thanks to Flintstones Vitamins) Sammy Sosa and a rookie Kerry Wood who struck out 20 Houston Astros in just his fifth career start.
Why 2016 Can Win It All:
The 2016 Cubs finished the regular season with the best record in all of baseball and a 17 1/2 game cushion atop the NL Central. The lineup had nary a weak spot as Kris Bryant played himself to an MVP season, Anthony Rizzo cemented his status as the unofficial team captain, and the Cubs had their last true lead-off hitter in Dexter Fowler. Ben Zobrist was a steady veteran presence and mentor to young players in Javier Baez, Willson Contreras, Jorge Soler, and since-maligned Addison Russell.
Jon Lester aced the pitching staff, but Jake Arrieta and Kyle Hendricks were the most dominant starters at points throughout the season. The bullpen featured Pedro Strop, Hector Rondon, Travis Wood, trade-deadline acquisition Aroldis Chapman, Mike Montgomery (who got the final out in Game 7) & a dazzling Carl Edwards who hadn’t yet had struggles settling on a windup. The NLDS against the Giants made me truly believe this Cubs team were championship contenders if a scalding hot start to the season hadn’t. There are enough memorable moments during both the regular and postseasons to warrant an entire series of blogs, but who could forget now-skipper David Ross’s iconic blast and Jason Heyward’s speech during the rain delay en route to an historic 3-1 series comeback? Recency bias aside, this team is rightly a heavy favorite.
Why 1998 Can Win It All:
Sammy Sosa’s 1998 home run race with Mark McGuire at the height of the steroid era arguably saved baseball. Though Sosa fell came up short in the dinger column, his team actually made the playoffs via the Wild Card. 1998 was also the season after Harry Caray died, so these Cubs were playing for something more. Throw in a stellar Mark Grace and some solid pitching thanks to Kerry Wood’s emergence and this 16-seed is an unusually formidable one. In a 7-game series, a young Kerry Wood could start two, possibly three games, so this match-up may be closer than many expect. Holy cow!
Series Prediction: 2016 in 6
The 1998 squad will steal two games in which Kerry Wood pitches on the back of solid offensive performances from Mark Grace and a Slammin Sammy who is all-too-eager to add to his absurd 158 RBI (in 159 games) total, but the offensive juggernaut that was the 2016 Cubs will be too much for a so-so 1998 bullpen to handle in a long series.
8. 1908 (99-55) vs. 9. 2015 (97-65)
I mentioned on the air that this was my favorite first round match-up by plenty. A 107 year gap separates the last Cubs World Series winning team before the curse was lifted from arguably the most (unexpectedly) fun Cubs team to watch in my lifetime.
Why 1908 Can Win It All:
Though it was this 06-08 dynasty’s third consecutive world series appearance, the 1908 team was arguably 3rd best of those teams. However, 5 of 6 starting pitchers boasting an ERA under 2 – dead ball era or not – is exceptional. Orval Overall, who I’m only mentioning due to his phenomenal name, was this team’s Opening Day starter. The legendary Mordecai “Three Finger” Brown was most recognizable name on the pitching staff, though. This team featured the fabled Tinkers-to-Evers-to-Chance double play combination. This Cubs team didn’t fall short against a dominant pitching staff like their first-round counterparts. Instead, they were the league’s dominant staff.
Loosely related: if you’d like a laugh, google 1908 Cubs Merkle’s boner. That phrase meant something far different in the early 20th century.
Why 2015 Can Win It All:
This Cubs team took the league by surprise by winning 97 games and opening their contention window a year earlier than nearly everybody expected. The most notable thing about this team was Jake Arietta’s all-time second half pitching performance capped off by a no-no in LA against the Dodgers that led him to the Cy Young (as if he hadn’t already cinched it up). This team also won plenty of games in walk-off fashion.
Though 97 wins was only good enough from third place in a stacked NL Central, this Cubs team beat the Pirates in the wild card game and then took down the Cardinals in NLDS. Kyle Schwarber’s moonshots in the playoffs, first into the water in Pittsburgh and the towering drive that landed atop the video board in right field in the NLDS over Jason Heyward are some more of my favorite memories from that year. The 2015 season kicked off the best 4-season stretch in franchise history.
Series Prediction: 2015 in 7
I’m going with my heart over my head with this one. 1908 has a lineup card stacked with some of the game’s greats, but Jake Arrieta was on another planet down the stretch and could very well begin a Madison Bumgarner-esque run though this tournament by pitching three gems in a 7-game series against a team that featured only one .300 hitter in Johnny Evers. If Mordecai Brown out-hurls Jake in any of those contests the scales could tip in 08’s direction, though.
5. 1989 (93-69) vs. 12. 2003 (88-74)
This match-up pits a team with Greg Maddux on it (1989) against a team that beat Maddux’s Atlanta Braves in the Division Series in 2003. It will be interesting to see whether the simulation favors a relatively young lineup and experienced pitching staff in 89’s team or a more experienced lineup and young, but remarkable pitching staff like 2003’s team.
Why 1989 Can Win It All:
It wasn’t his MVP year, but this Ryne Sandberg-led team won 93 games to finish first in the NL East en route to an NLCS appearance against the Giants. The 1989 Cubs were significant due to the emergence of a young Greg Maddux & Mark Grace. The lineup was so stacked that hall-of-famer Andre Dawson had the 7th best batting average (.252) out of the 8 every-day position players. Maddux, Matt Bielecki, and Rick Sutcliffe notched 19, 18, and 16 wins and young all-star reliever Mitch Williams tallied 36 saves. This team also featured NL ROY Jerome Walton, Shawon Dunston, and Dwight Smith.
Why 2003 Can Win It All:
88 wins was good enough for the Cubs first ever NL Central division title in Dusty Baker’s first year at the helm, but the 2003 Cubs didn’t stop there on their way to a now-infamous NLCS. 03 featured a pitching staff comprised of Kerry Wood, Mark Prior, Matt Clement before he became a bust, a young Carlos Zambrano – who each won at least 13 games – a dependable closer in Joe Borowski, and a firey Kyle Farnsworth out of the pen.
Who’d the lineup feature? If you guessed Moises Alou, urine luck. A well-into his 30s Sammy Sosa was still a force to be reckoned with at the plate, while Eric Karros, Cory Patterson, Aaramis Ramirez, and Mark Grudzielanek each swung the bat effectively that season. The team got an unexpected spark from an aging Kenny Lofton – who just looked like he wanted it more than anyone else – down the stretch and throughout the playoff run. A 5/12 upset is a popular pick, and for good reason. This team was just an all-time collapse from making history.
Series Prediction: 1989 in 6
The 1989 Cubs were first in the National League in both runs and hits. Even though the 2003 team won more games in the NLCS, I’m more comfortable favoring a playoff pitching rotation of Greg Maddux, Rick Sutcliffe, and Matt Bielecki than a promising, though at times inconsistent, starting rotation (2003) that didn’t always get great run support. The 1989 team’s batting lineup and positional depth with would just be too much for a young staff (manged by a so-so X’s and O’s guy in Dusty Baker) to handle.
4. 1907 (107-45) vs. 13. 2017 (92-70)
This pairing is another that spans more than 100 years and features a World Series Champion 1907 team against a 2017 team that suffered a slight World Series hangover. Both of these teams were phenomenal at home, but the 1907 squad was also dominant on the road en route to the franchise’s first World Series crown.
Why 1907 Can Win It All:
This roster was a formidable one and bounced back after a shocking loss to the White Sox in the 1906 World Series (more on that later) to win the pennant by 17 games. They weren’t able to sweep the pesky Tigers in the World Series – the first game was deemed a tie after 12 innings – but the formidable 07 pitching staff allowed 1 run each in games two through five to secure a championship in front of an apathetic visiting crowd of just 7,370 at Bennett Part in Detroit. The previously-mentioned Orval Overall paced the hurlers with 23 wins and 141 Ks, but his 1.68 ERA was good for just fifth-best among a starting rotation that featured six guys with ERAs under 1.7. No every day player hit above 2 home runs or .293, but at the height of the dead-ball era dominance on the defensive side of the ball was enough for the 1907 team to go down in the history books.
Give this staff just a smidge of run support and they could hang a banner.
Why 2017 Can Win It All:
After a slow first few months of the season, this Cubs team heated up in July and August on their way to a second consecutive NL Central crown. They won an exciting NLDS against the Washington Nationals stealing games started by Stephen Strasburg and Max Scherzer, but got shut down by a considerably better Dodgers team in the NLCS. Wade Davis did a wonderful job replacing a departed Aroldis Chapman in the closer role. The midseason acquisition of Jose Quintana showed Cubs fans that the front office didn’t want 2016’s championship to be a flash in the pan.
Aside from the glaring hole in the lead-off spot after Dexter Fowler’s departure, the roster didn’t change up that much from 2016. Without a consistent lead-off bat, winning 92 games with a still-developing core is admirable as Willson Contreras & Javy Baez showed more consistent flashes of brilliance. A 7 game series is a lot less of a grind than a 162 game season plus the playoffs, and the 1907 Cubs aren’t the offensive buzzsaw that the 17 Dodgers were, so if the table-setters can perform this squad could make an unexpected run.
Series Prediction: 1907 in 6
The 2017 Cubs were just too inconsistent & willing to take their foot off the gas after a World Series title. On the other hand, the 1907 team had something to prove after coming up short in the World Series the previous season. That drive, though not quantifiable in our simulation, should be enough to beat a team that lacked the necessary urgency to get to the promised land. Additionally, if anybody on the 17 pitching staff could give up longballs a dead-ball era team, it would be John Lackey.
6. 1969 (92-70) vs. 11. 1932 (90-64)
Speaking of teams who were too confident and ran out of gas at an inopportune time late in the season, the 1969 Cubs that lost 17 of their last 25 games are considered by many to be the best team ever to have not made the playoffs. They face off against a Cubs team that lost the World Series to Babe Ruth’s Yankees.
Why 1969 Can Win It All:
Not only were these Cubs the best team to ever finish second/not make playoffs, according to my dad they’re the best team ever to not make the World Series (how’s that for some #Jimmermetrics?). As crazy as that sounds, this squad featured four hall of fame players and a HOF manager: Ernie Banks, Billy Williams, Ron Santo, Fergie Jenkins, and Leo Durocher as the manager. Though this team got too cocky and choked away a comfortable division lead down the stretch, I’d put their lineup up against any Cubs team ever. With Ernie at first, Ron Santo at third, Don Kessinger at short, the good Hundley (Randy) behind the plate and Billy Williams roving the outfield this team was good enough to make history.
A name I hadn’t even mentioned yet, Bill Hands, won 20 games, tossed 300 innings, and amassed a team-best 7.9 WAR for the season. In a long series, which this team shouldn’t need in this first-round matchup, Fergie Jenkins would pitch 2-3 games and Hands would be nearly as stifling in his appearances. Even as a 6-seed, the team that broke a 5-year old papa Norland’s heart has a legitimate shot at virtual glory.
Why 1932 Can Win It All:
This team was swept in the World Series by a 107-win Yankees team that featured a dazzling TEN future members of Cooperstown: nine players and their manager, Joe McCarthy. Now they’re matched up with a team with four HOF players and a HOF manager? Talk about bad matchups. A young Lon Warneke was a force to be reckoned with on the mound and four everyday players hit over .300, so they may not roll over so easily. This is a team that still made a World Series after their manager was replaced in August, so the chip on their collective shoulder may be enough to push them further than anticipated…
Series Prediction: 1969 in 4
…but against the stacked team that made my father a lifelong Cubs fan, I don’t see that happening. The 1932 team was swept in the World Series, and I envision the same happening in the first round of the 2020 Crosstown Centurion.
3. 1984 (96-65) vs. 14. 1885 (87-25)
The 1885 Chicago White Stockings (they would change names a few times before becoming the Cubs) are only seeded so low because they didn’t win a championship. They also didn’t lose the championship. As it turns out, they TIED the St. Louis Browns in that wayward season’s championship series 3-3-1. There are no ties in 7-game series run by computer simulations, so this matchup against a 1984 team that featured an MVP in Ryne Sandberg and a historic second-half pitching performance by Rick Sutcliffe will produce a clear victor. That much I can guarantee.
Why 1984 Can Win It All:
Another dad-favorite: the 1984 Cubs, featured Ryne Sandberg in his MVP year. He also won his first of seven Silver Slugger awards that season. Rick Sutcliffe won Cy Young based on an absurd (but not quite Arietta-esque) second half & Lee Smith owned the 9th with 33 saves. After a mid-season trade from Cleveland, Sutcliffe went 16-1 with 7 complete games and 155 Ks in 150 1/3 innings pitched. A lot would have to go right in this tournament for a 1984 Sutcliffe and 2015 Arietta pitching duel to happen, but that matchup would be one for the internet ages.
More on the 84 NL East Champions, courtesy of my pops: NBC stole home-field advantage from the Cubbies because of TV rights in an NLCS that the Cubs lost 3-2. Sandberg and Dernier were the best 1-2 in the league. The old guys (who should be in HOF according to him) kept the Cubbies in the hunt until Rick Sutcluffe showed up. That season is also when Dennis Eckersley drank himself out of Chicago on his way to a hall-of-fame career – his nickname was upper deck Eck. This team ended a playoff drought that dated back to WWII, and Tony Gwynn was an absolute magician in the heartbreaking NLCS.
Why 1885 Can Win It All:
The 1885 Chicago White Stockings accumulated a lucky .777 win percentage and may just become your favorite team that you had never even heard of. John Clarkson aced the staff with a 53-16 record, a 1.85 ERA, and an absurd 12.8 WAR. On the other side of the coin, 16 of team’s 25 losses fell on one pitcher. If you take one thing away from this blog, let it be this: do some of your own research on the 1885 Chicago White Stockings. It’s an internet rabbit hole you won’t regret going down.
A simulation that doesn’t care about eras throughout baseball history may put a lot of weight on such a dominant winning percentage. A solid 3-man rotation is all this team may need to make a splash 135 years in the making. Give this team actual baseball gloves and they very well could be unstoppable. They were managed by the legendary Cap Anson and featured some all-time great names: Silver Flint, Wash Williams, Billy Sunday, and King Kelly. That’s a lineup card that would be a blast to read aloud!
Series Prediction: 1984 in 6
The mystique behind the 1885 team may actually hurt it. If they had actually won the championship series instead of merely tying it I may be more inclined to go with my heart over my head here, but a lineup full of phenomenal names won’t get the job done against MVP and Cy Young award-winners. However, John Clarkson’s stat-line and the fact that the White Stockings won nearly 80% of their games (no matter what the level of competition may have been 20 years after the Civil War ended) is nothing to scoff at. Since the 84 team gets seven games to decide a series instead of five, they’ll take this one.
7. 1945 (98-56) vs. 10. 1935 (100-54)
This matchup is intriguing for a couple reasons. It is the only first-round pairing of teams that played within a decade of one another, so the physical makeup of the player should be more even than any in our simulated contest. In addition, both teams lost to the Tigers in the World Series.
Why 1945 Can Win It All:
Stan Hack swung a serious stick, slashing .323 for the year and every starting pitcher was in double digits in the win column. This team went 7 games in the World Series, but fell short to the Tigers. Dropping World Series’s to the Tigers became a pattern that would’ve driven Cubs fans in the early half of the 20th century mad. The 1945 season’s legacy is still alive due to the fact that an unnamed podcast host’s grandfather’s uncle decided it would be a good idea to try to bring his Billy Goat into Wrigley Field.
Why 1935 Can Win It All:
The 1935 team added some star power to go along with a lot of the same guys as the 1932 team that made it to the Fall Classic. Billy Herman was a 10-time all-star that led baseball with 227 hits and 57 doubles, amassing 7 WAR that year. Augie Galan and Billy Herman both didn’t miss a game and collected over 300 total bases, and three starting pitchers ate up 240+ innings. This team has arguably the most eye-popping individual stats on the Cubs side of the bracket. If fantasy baseball existed back then you couldn’t have gone wrong with many of these Cubbies. The 1935 squad was the last Cubs team to win 100 games before 2016. They got there in large part to a 21 game win streak late in the season that spanned nearly all of September. If they were to duplicate such a stretch the 35 team would win the entire side of the bracket.
Series Prediction: 1935 in 5
Though the simulation may discount this fact, I’m less impressed by the 1945 team due to many of the MLB’s superstars still adjusting to life back in the United States after WWII ended. The 1935 team can reel off wins like no other in franchise history and features an entire lineup with an OBP over .300. Only one everyday player hit below .275 that season. The 1935 team could be the most under-the-radar double-digit seed in this tournament.
2. 1906 (116-36) vs. 15. 2008 (97-64)
The 2008 Cubs were often referred to as the “Next year is here” team. It had been 100 years since the last Cubs World Series win, and Cub fans really believed that this would be the group to reverse the curse. So why aren’t they seeded higher? They couldn’t win even a single playoff game on their way to getting swept in the NLDS by the Manny Ramirez-led Dodgers. The 1906 team was also a disappointment, but not until putting the most dominant regular season in franchise history together en route to a World Series appearance.
Why 1906 Can Win It All:
By most any metric besides the one that matters most, this was the best team of the 1906-1908 dynasty. Unfortunately, they lost the World Series to those pesky White Sox in what the newspapers of yore detailed as unthinkable entering the series. It was both teams’ first World Series appearance and the surprising result has fueled over 110 years of trash talk.
The 1906 Cubs finished 20 games up in the pennant chase. Their .763 winning percentage is the highest in MLB history. As previously mentioned, these few Cubs teams lacked power in heart of deadball era, but it didn’t matter. Led by hall-of-famer Mordecai “Three Finger” Brown’s legendary 1.04 mark, 5 of 6 starters pitched themselves into the record books with sub-2.00 ERAs. It was an absolutely dominant team, but for four days in the fall of 1906 in Chicago, it just wasn’t enough.
“Dominant doesn’t pay the bills,” – Mayor of section 509.
Why 2008 Can Win It All:
While I was too young to realize the significance of the 2003 Cubs, the 07-08 playoff teams were the groups that sucked me in to Cubs fandom. Running through the 2008 NL Central champs roster brings back fond memories. Derek Lee is an all-time underappreciated Cub. Ryan Dempster and Ted Lilly both notched 17 wins, and Carlos Zambrano was not far behind with 14. Aaramis Ramirez led the team with 111 RBI. Alfonso Soriano shared the outfield with Jim Edmonds, Kosuke Fukudome, and Reed Johnson. Geovany Soto won the ROY at age 25. As an undersized, opposite-field hitting young ballplayer I absolutely adored the Ryan Theriot-Mike Fontenot double-play combination up the middle.
Kerry Wood coming out of the bullpen to save 34 games was a fun experiment, but breaking the 100 year curse was not meant to be. I correctly remembered when recording that this Cubs team got really hot in August, but I overshot the amount of games they won by a few. It turned out they went 20-8 that month, but if they can channel that mojo again they’ll ride that momentum as far as it’ll take em.
Series Prediction: 1906 in 7
The most dominant regular-season Cubs team ever getting taken to 7 games by a team that didn’t even notch a playoff win is admittedly a prediction rife with nostalgia. I laid off the crazy pills in just enough time to pick the rightful winner of this matchup, but I don’t expect 1906 to move on without a battle.
Crosstown Centurion Cubs Champion Prediction:
1969 (6 Seed)
There are no watering holes to frequent with big division leads in computer simulations, so the team that felt they had already won something only to spectacularly collapse down the stretch should fare better in this simulation. Nick called them a Darkhorse, I’m calling them my pick to represent the Chicago Cubs in the Crosstown Centurion Championship Series. Call it a nod to my dad & grandpa, but Ernie & Ron need themselves a championship of some sort.
Crosstown Centurion Cubs Darkhorse Candidate:
1935 (10 Seed)
Six starting pitchers ranging in age from 23 to 36 collected double-digit wins. Every regular position player (aged 18-34) besides one hit over .275, and the first guy off the bench hit .275, clubbed 22 doubles and drove in 62. It didn’t matter the age. It didn’t matter the position. This team flat out performed and put up eye-popping numbers on both sides of the ball.
Oh, by the way, the 1935 Cubs had five HOFers: an aging but still effective Kiki Cuyler in the outfield, a 34-year-old Gabby Hartnett behind the dish who led the team with a .344 average, a young aforementioned Billy Herman who was right on Gabby’s heels hitting .341, outfielder Chuck Klein, and utility-man Freddie Lindstrom. A potential Elite 8 matchup against the 1969 team could be a simulation tens of people talk about for weeks to come.