Bracketology: Best Players in Chicago Cubs History Determined by the Madness

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COMMENTARY | This is one of those important pieces of Internet-era journalism meant to cause Chicago baseball fans with that same blue hat to scream at each other in Wrigleyville bars this weekend as they watch the real bracketology play out.

It's an eight-player tournament inspired by the madness and steeped in a melding of the senseless and statistical. It's a one-and-done tournament format to determine the all-time greatest Chicago Cubs baseball player.

And the conspiracy rumors are true: The dictatorial committee has taken some liberties with the seeding in order to boost ratings.

No bunting allowed in the comments zone.

Brush-backs encouraged.


No. 1 Ernie Banks

No. 2 Ryne Sandberg

No. 3 Ron Santo

No. 4 Billy Williams

No. 5 Fergie Jenkins

No. 6 Frank Chance

No. 7 Greg Maddux

No. 8 Harry Caray


Andre Dawson only played six seasons with the Cubs. Mark Grace had more hits in the 1990s than any other Major League Baseball player and is my favorite player of all time, but he's banned from the tournament this year because of rules violations.

Hack Wilson might have driven in a MLB single-season record 191 runs in 1930, but he only played six seasons in Chicago. Cap Anson might have had a .331 career average, but he technically played for the Chicago White Stockings before they became the Cubs. Mordecai Brown's three-finger act is proof enough that players from his era couldn't cut it today. And Sammy Sosa, well, WWF wrestlers need not submit their tournament resumes for review.


The Bud Man drained a buzzer-beating 3 over the outstretched phantom fingertips of Mordecai "Three Fingers" Brown in the play-in game to get here. Some would argue Harry Caray is ineligible for this tournament because he was not, in fact, a baseball player. But we're talking about an organization in which a video assistant finished second in this spring's bunting tournament, so anything is possible.

Banks sends Harry back to the booth pretty easily in this matchup after Harry has to take the mound with a moderate buzz and face the power-hitting shortstop.


Williams' career numbers are impressive, given the era he hit in. He clubbed 426 home runs and, as a left-handed bat in a lineup with Banks and Santo, caused all sorts of matchup problems for opposing pitchers. He probably deserved an MVP in 1972 over Johnny Bench when he hit .333 to win a batting title with a .606 slugging percentage, 37 home runs and 122 RBIs.

But Jenkins had six consecutive seasons of 20 wins, as well as a Cy Young in 1971 when he threw 30 complete games. You read that right -- 30 complete games. He's also one of three pitchers in the history of baseball to strike out 3,000 batters while walking fewer than 1,000. The others? Pedro Martinez and the No. 7 seed of this tournament, Maddux, who pitched 508 more innings and still managed to keep his walk total under 1,000.

Williams flies out to the warning track, and Jenkins wipes the sweat from his brow as he narrowly advances to the Final Four.


The righty-righty matchup between former teammates favors the pitcher, even if Sandberg played almost his entire career for the Cubs. Four consecutive Cy Youngs vs. one MVP. Eighteen Gold Gloves for Maddux vs. nine Gold Gloves for Sandberg. Their retired jersey numbers fly together at Wrigley Field, but one player is in another league.

Sandberg went to 10 consecutive All-Star games and had seasons of 40 home runs and 50 stolen bases as one of the all-time great second basemen, but he loses to Maddux on a tough-luck first-round matchup after the committee slotted Maddux in at No. 7 because he spent so many years away from Chicago.


Chance might have been able to give himself the steal sign in the 1908 World Series as a player-manager, and he might be the organization's all-time leader in stolen bases. He might be the only player-manager in the history of the game to win two World Series, but there's a reason he doesn't have a statue outside Wrigley Field and Santo does. Plain and simple, Santo was a better baseball player in a better era.

Santo runs out to third base, clicks his heels together, and advances to the Final Four.


Another righty-righty matchup between former teammates should favor the pitcher, but Banks didn't string together four 40-plus home-run seasons off of only southpaws. And his back-to-back MVPs in 1958 and 1959 hold up against the best consecutive seasons any shortstop has ever had at the plate.

Banks advances to the title game with a shot at a ring he never won on the diamond.


Santo's offensive numbers do not look staggering when looked at by today's standards, but he played in a pitchers' era. He hit .277 with 342 home runs, his five Gold Gloves might not accurately quantify just how good he was with the leather, and he was a nine-time All-Star. He's one of four Hall of Fame third basemen with 300-plus home runs and 1,300-plus RBIs.

But Maddux was the best player in baseball during the worst era for pitchers. That run started with the Cubs with his first Cy Young in 1992. He's the greatest control pitcher the game has ever seen, and he's one pitcher even the selective Santo couldn't draw a walk against.

Maddux retires Santo to the Cubs' radio booth, where Santo touched another generation of Cubs fans and catapulted his iconic status in the organization to new levels.


The best part about this matchup is each participant would lobby for the other if asked to weigh in on this question of greatness.

Banks hit 512 home runs at a time when shortstops flat out did not do that. He's a Cubs lifer, having never worn another MLB uniform. He is Mr. Cub.

But Maddux's numbers border on the insurmountable. He won 355 career games. He won at least 15 games in 17 consecutive seasons, despite that stretch including a pair of strike-shortened seasons. No one else in the history of baseball has done that, and it's hard to imagine it ever happening again. Six of those 15-win seasons happened with the Cubs. His numbers from 1992-98 amount to the greatest seven-season stretch of pitching baseball has ever seen. Past his prime, he returned to record his 300th win and 3,000th strikeout with the team that drafted and groomed him. Only 10 pitchers have accomplished both feats.

Greg Maddux is the most valuable baseball player to ever wear a Cubs uniform. He will be a first-ballot Hall of Famer and he might come closer than anyone to doing it unanimously. And the Cubs let him go. In his prime. Maybe this has something to do with the organization's World Series drought. Maybe it's fitting the greatest player the Cubs have called their own had the best years of his career in a different uniform, representing what could have been.

With a 1-1 count, Banks jumps on a fastball but pulls it just inches left of the left-field foul pole. Maddux gives off a self-deprecating look to acknowledge he got away with one. And on the 1-2 pitch, Maddux paints the black on the outside corner to catch Banks looking.

Now let's all scream at each other about it while Maddux walks back to the dugout with his trademark quiet confidence.

Kevin Chroust has covered baseball and various other sports since graduating from Colorado State in 2005. He has been following the Cubs since age six when Mark Grace hit .647 in the NLCS against the San Francisco Giants. You can follow Kevin on Twitter @kevinchroust.

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