March 12, 2015

(Exclusive for Cubsquest)

Cool and Cubs are words that rarely go together, so putting together this admittedly subjective list was a bit of a challenge.  There is little doubt that the likes of Gabby Hartnet, Charlie Grimm, Phil Cavaretta and Hack Wilson were not only great players but pretty cool dudes. And who wouldn’t want to down a few with Tinkers, Evers and Chance? But unfortunately the editors of Cubsquest weren’t around to observe and subsequently offer the first hand anecdotes covering the entirety of Cub lore that would connote true “cool”, so the following list will only cover the last half century of cool cats to roam within the ivy covered walls.

The following roster covers the last 5 decades of the smoothest players at each starting position, a full bench and pitching staff, guided by kick ass managers, coaches, GMs and of course vividly described for your pleasure by the cream of the crop broadcasters…


Harry Caray: The ultimate no-brainer starts our list. Harry isn’t only the coolest Cub broadcaster ever, but of all time on any team anywhere. The Wrigleyville we know and love today wouldn’t exist if not for Harry. The stories are legendary, and the recent discovery of a Caray diary, documenting 200+ days of binge drinking with the likes of Jack Benny confirm that. But lest us not forget that no one, with the exception of the peerless Vin Scully called a better game or did so with more passion then Harry. Cool-ass moment(s):  Of course there’s the historic on–air inning with President Ronald Reagan and his penchant for creating his own brand of humor during dead spots in the game; “ Whaddya know “Matlack is facing Madlock” or Sosa spelled backwards is “Asos”, but for this writer it was the 3AM happenstance meeting on Rush Street at a friends bachelor party when upon introduction to Harry (who had a gorgeous young lady escorting him) he just growled “Don’t do it Son!”

Vince Lloyd: On the radio side he’s sometimes a forgotten man, but any Cub fan who listened intently during that golden 60’s-70s era, knows just how good he was. An ex-Marine World War 2 vet, Lloyd partnered with Hall of Famer, good kid Lou Boudreau for 20 years on WGN radio to set the standard for Cub fans to this day. Cool-ass moment: Vinnie’s interview of President Kennedy in 1961 was the first baseball on TV interview of a standing President.

Pat Hughes: No one could’ve followed up the Lloyd era as well as current Cubs voice Hughes, whose smooth as silk vocal intonations, deliver old school descriptions of the actions. With an uncanny ability to build an instant rapport with whoever WGN tosses his way – since his iconic partner Ron Santo passed – Pat has had the unseemly task of making the likes of semi-articulate amateurs like Keith Moreland and Ron Coomer come across credible and listenable, something he has done seamlessly. Cool-ass moment: His vivid, verbose pregame set ups; “Today the Cubs are sporting their road grey uniforms, brilliant royal blue letters outlined with bright white piping…”


Dallas Green: Anyone paying attention over the past five decades, realize the Cubs 100 + year futility /drought has more to do with the idiots running the team than any goat curse. Green however was a moment of clarity that the then new ownership of the Tribune company displayed, and his stormy six year tenure completely changed the complexion and swagger of the team, creating the first serious contender since the Durocher teams of late 60s. Cool-ass moment: His first order of business; changing the smiling Cub logo posted on the team’s uniform sleeve, into a mad pissed off version – and don’t call them the Cubbies, damn it!


Leo Durocher: You can’t have a cool team without a manager who walks the walk, and in modern day Cub lore, the line forms behind Leo. Many fans – including the editors of, had the disease thrust upon them in the Durocher era, when the team actually played and functioned like a serious 1st division contender. This was no coincidence, as upon taking the helm in the mid 60s, Leo immediately established that a new sheriff was in town; one that favored winning. He famously coined the term “nice guys finish last” and lived it. Though his Cub teams fell a tad short they are still the template for success in Wrigleyville.  Cool-ass moment: Recruiting Mr. Ed, Herman Munster, Jethro and Ellie Mae Clampett to play for the Dodgers – a team he ironically never managed (see Cubsquest “Vintage Video” for full episodes)

Herman Franks: Though he only had one team finish .500, the 77’ Cubs were one of these most entertaining teams in Cub history, and Herman one of the most colorful skippers. It’s no surprise that the gruff, cigar chomping Mormon from Salt Lake, Utah learned his trade from Durocher himself, as Leo’s Bench coach with the New York Giants. He was so wealthy that he didn’t need the job, and as such he managed to please HIM.  Cool-ass moment: Resigning in 1979 because “there wasn’t enough money” to listen to the further “whining” of journeyman OF Mike Vail.

Don Baylor:  After years of non-descript milquetoasts, the Baylor hiring in 2000 marked the first serious attempt to implant an actual in-demand leader by the Cub front office since the Jim Frey era of the mid 80s. Baylor was 1997 NL Manager of the year with the Colorado Rockies and was being hotly pursued by other clubs when he chose to bring his no nonsense style to the North Side.  Cool-ass moment: Telling over-rated diminutive prospect Corey Patterson – who fancied himself a power hitter – and inexplicably compared himself to Wille Mays: “Willie Mays could bunt, he had game. You’re more like Odibe McDowel”, a failed prospect- to motivate the diminutive outfielder that he should implement small ball into his game.

Joe Maddon:  The current skipper on the Northside may just be the best ever to fill out a line-up card. But Maddon’s on-field prowess and clubhouse finesse’ is only complimented by classy demeanor and his verbose, eloquent delivery, making his post game press conferences must-hear daily events. Cool-ass moment: Meeting Theo Epstein and Jed Hoyer for the first time in a Florida trailer park in his mega-motorhome tabbed “Cousin Eddie”.

Oscar Acosta: Only one pitching coach was cool enough to make the list and not necessarily for his coaching skills. Like Baylor his manager, Oscar was just a total no-nonsense badass. He rustled cattle in Mexico and put up with no crap from pampered pitchers.  Cool-ass moment: Calling out porky rookie pitcher Ruben Quevedo for throwing off-speed junk during the early innings of a start; “That garbage may play in the Mexican league, but it doesn’t up here!”, or when Carlos Zambrano’s age came up he said ‘he’s HOW old? 22? He was older than that when I had him in the minors 3 years ago.”

Dave McKay: After years on Tony LaRussa’s Cardinal staff, McKay brought needed fundamentals to the hapless Cubs. Cool-ass moment:  Turning defensive liability Alfonso Soriano into a quasi-legitimate outfielder.


Ferguson Jenkins:  A cool customer on and off the field, the lanky right-hander became the template for what a starting pitcher should be. A couple Cy Young awards, over 300 wins and 3000 + Ks put him amongst the all-time greats.  But perhaps most impressive were his 267(!) complete games. Guy could also rake (6 HRs in 71’) and run the bases.  An accomplished basketball player, Fergie spent a few off-seasons jamming with the Harlem Globetrotters. Cool-ass moment:  Drinking whisky and BS-ing with Billy Williams in their tiny rustic cabin while moose hunting in Canada, in the winter of 1972. (As seen in 1974 Donald Britten Documentary “King of the Hill” posted on under Vintage Video)

Greg Maddux:  His Hall of Fame pitching career is based on the bloodless, cerebral calm of a sniper, but Cub fans remember a rail thin, highly emotional hard thrower -who would swear quite loudly after deliveries he was less than enamored with. Mad Dog was a free spirit whose premature departure from the team is perhaps the darkest hour in modern Cub history, and has the hapless responsible GM, Larry Himes still afraid to show has face in the city limits (rumor has it he’s hanging out in North Korea with Dennis Rodman and Steve Bartman) Cool-ass moments:   Many… After a deluge rained out the Cubs very first night game in 1988, Maddux used the infield tarp as a slip and slide; his very audible cussing after every pitch he’d throw that didn’t please him… the list goes on.

Rick Sutcliffe: A soft-spoken gentleman in mixed company and an assassin on the mound, the Red Baron had perhaps the most dominating season ever by a Cub starter (16-1) during his 1984 Cy Young Campaign. Even after shoulder wear and tear stole his plus fastball, “Struggle-cliffe” always found a way to get her done.  Cool-ass moment: The 440 foot bomb he launched off Eric Show in game one of the 84 NLCS, while tossing a 12-0 shutout.

Rick Reuschel: Big Daddy may have had his best seasons with the Giants after he left, but the rotund right hander was the ace on many awful Cub teams, where he also displayed his prowess at the plate and on the base paths. Cool-ass moment: Winning the first game of a Double header on the mound then scoring the winning run of the second as a pinch runner.

Ken Holtzman: To this day, Holtzman is the only quality lefty starter to come out of the Cubs farm system in the last 50 years. He’s also the only Cub pitcher to toss multiple no-hitters.  Cool-ass moment: Driving to Wrigley on Saturdays during his military reserve duty sporting his Marine fatigues in his green ’67 Cadillac Eldorado.

Ted Lilly: Theodore Roosevelt Lilly turned down more money to come to Chicago to play. Why? The career American Leaguer wanted to hit. He famously was seen hypnotizing a large beetle and putting it first on coach Gerald Perry’s shoulder, then moving it to his cap during the inning in the dugout. Perry just about jumped out of his skin when he saw the mammoth insect. Cool-ass moment: Running into Cardinal all star (and future Hall of Famer) catcher Yadier Molina at the plate, scoring the run- AND knocking Molina out for the season. Why he wanted to play in the National League in the first place; real baseball is played there.

Randy Myers: One of the original “nasty boys”, Myers lead the NL in saves 2 of the 3 seasons he pitched for the Cubs. Cool-ass moment:  Tackling then pummeling some loser who ran on the field toward the mound after nailing down a save at Wrigley, or his deactivated hand grenade in his locker.

Turk Wendell: Perhaps the most colorful Cub ever and filled with quirks – Turk would leap over every foul line, wave to the center fielder before delivering the first pitch of each inning, chew licorice then brush his teeth in the dugout. Cool-ass moment: An avid hunter – Turk once tracked a wounded deer through a car wash with his cross-bow.

Rod Beck: Shooter didn’t have a lot in the tank stuff-wise when he came to the Cubs in 98, but grit and toughness racked up 51 saves and a NL central title. He also parked his luxury motorhome outside the minor league complex he rehabbed in and threw memorable parties there. Cool-ass moment: Beck was on the mound for the Brant Brown Milwaukee meltdown and took the lead in pulling the distraught clubhouse together. 

Terry Mulholland: He started, set up and closed in 70 appearances providing the glue on the pitching-thin team that was instrumental in the 1998 post-season push. Cool-ass moment:  A career .111 hitter, Terry was an unlikely offensive force in 98’, hitting .294, including a leg double providing the winning run in a key September game.

Mitch Williams: Wild Thing lived up to his name in just about every aspect of his game. Famous for his type-rope walking multiple-pitch saves; Williams would commonly both walk the bases loaded and strike out the side. He also gained more than one save by picking off a runner to end the game. Cool-ass moment: Cracking a three run HR off Randy Meyers in a 1989 Wrigley night game versus the Mets.


1B – Mark Grace: A Three time all-star with 4 Gold Gloves, Gracie lead all of MLB in hits and doubles for the decade of the 90s. Old school in every way, he smoked, drank and didn’t wear batting gloves. His .647 average during the 89 LCS is one of the all time big stage coming out parties for a Cub hitter. He was also mega loyal to a team that never really believed in him, acting as his own agent and signing 12 one year contracts. Cool-ass moment: After any Wrigley night game, smoking Marlboros and downing Buds with fans at Murphy’s Bleachers. (Even when dating Hollywood babe Janine Turner)

2B- Ryne Sandberg:  He hardly said a word throughout his impeccable all-star career while basically re-establishing the gold standard at the second base position, but Ryno was the team’s stealth prankster.  If there was a hot foot to be given or a rookie to be hazed, Sandberg was the man. This fiery personality came to fruition during his managerial stint in the minors where he was legendary for his umpire tirades.  Cool-ass moment:  The nationally televised ‘Sandberg game’ after which Cardinal manager Whitey Herzog dubbed him “Kid Natural”.

SS- Ernie Banks:  He played 20 seasons for the hometown and defined class from day one. In a segregated era, he didn’t bitch whine or pout, rather letting his bat, glove and demeanor do the talking. Never without a smile, Ernie coined the iconic mantra “Let’s play two!” He’s Mr. Cub for a reason.  Cool-ass moment: May 15, 1970 when Ernie became the first Cub to ever hit 500 Homers… hard to top that!

3B- Ron Santo: Captain Ron is almost as well known for his charming non-secquitirs in the booth as for his rugged 3rd base play. The All Star was a lightning rod to fans and media alike, with his vocal, fiery heel clicking ways. When diabetes ravaged his body taking both his legs, he soldiered on like Monty Python’s black knight, (“It’s only a flesh wound!”) The photo of him at Shea with the black cat darting in front of him in ’69 is indelibly etched in every Cub fan’s psyche. Cool-ass moment: Screaming “Oh NO!!” when Brant Brown drops a fly ball to blow a 9th inning lead in key September 1998 game in Milwaukee.

LF- Billy Williams:The sweet swinging gentleman from Whistler. Alabama. Billy is probably the best pure hitter to ever don the blue pinstripes. A definitive number three with an unflappable inconsistency that never seemed to slump, even his minus defensive skills would rise to the occasion with the game on the line – like catching Hank Aaron’s blown-back-in the park home run during Ken Holtzman’s no hitter.  Cool-ass moment: Before every AB, stepping up to the plate, spitting out his gum and hitting it with a practice swing.

 CF- Rick Monday: Monday patrolled Centerfield at Wrigley for five seasons with grace and panache’. A rare combination of defense and power, he glided effortlessly to everything hit his way and set the team record for HRs in a season by the position (32). Cool-ass moment: Former Marine reservist Monday rescuing the American Flag from being torched by protestors in Dodger Stadium.

RF- Andre Dawson:  After wasting away up in Montreal as basically the best all around outfielder in the game, Dawson staked out then Cub GM Jim Frey and made him an offer he couldn’t refuse. Pay me want you want, just make me a Cub. He did, and Andre put up sick numbers, becoming the first National League MVP from a last place team. Cool-ass moment:  Being yanked out of the vines by Kerry Wood in State Farm commercial, saying “What year is it?”

C- Randy Hundley: Any catcher with a nickname the Rebel that threw tantrums with such pinache’ you want on your team. Cecil – Randolph is also one of a very select few credited with revolutionizing the catching position by catching with one hand. Cool-ass moment: Seemingly setting the high jump record in full gear after the ump blew a late inning call in a key September game in 1969.


Bill Buckner: Billy Buck came to the Cubs in a trade for the popular Monday, and wound up having some of his best seasons. An exercise in unabashed grit and determination – basically playing on one good leg – Buckner out hustled and out performed just about everyone in the NL during his north side tenure. The fact he is known for the “Mookie-squib” that leaked through his legs in the 86’ World Series while playing for the Red Sox is one of the great travesties in baseball history. Cool-ass moment: The countless times he threw his bat to foul off a pitcher’s pitch, then drew a key walk and limped to first base on his taped up gimpy legs and immediately stole second before the opposing pitcher knew what happened.

Dave Kingman: So hideously unpopular – even with his hometown team – “Kong” was also larger than life in Cub pinstripes. And his numbers showed it, posting some of his best seasons here. His 48 – 115 – .288 campaign in 1979 was MVP worthy, (he finished 11th, behind the likes of Ray Knight and Kent Tekulve) and who could forget in getting there his uncanny ability to play small ball, dropping numerous surprise bunts down the third base line (paying attention Castro, Barney anyone?…)  Cool-ass moment: His legendary mammoth moon shot down Kenmore avenue is still THE Wrigley homer all are compared to.

Jose Cardenal:  A five tool player + one (his Baseball acumen was Jeter-esque) – and though they were little tools – Jose is still one of the most beloved Cubs of the last 50 years. Cool-ass moment:  Being caught by the WGN cameras stashing a ball in the Ivy between innings of a game.

Joe Pepitone: Pepi eventually replaced Ernie Banks as the Cubs every day first baseman in the early 70s, and brought some much needed Yankee swagger into the clubhouse. Cool-ass moment: Grooming his bad-ass Sopranos style gangster coif. with his high-powered hair dryer.

Bobby Murcer: Once deemed the heir apparent to Mickey Mantle during his days with the Yankees, Murcer came to the Cubs in the twilight of his career and brought with him an effortless pro’s game. Cool-ass moment: His patented delayed steals in key situations, usually standing up.

Gary Matthews: Perhaps the most clutch player on the most clutch Cub team of the modern era, “Sarge” truly earned his nickname as the undisputed leader of the 84 squad.  Cool-ass moment: Smacked two homers in game 1 of 1984 NLCS.

Nomar Garciaparra: “Glass” was on the DL as much as he played and he may have been a shadow of his All-Star self when he did so, but Nomar brought a regal barring rarely felt at Clark and Addison. Cool-ass moment: Drilling a single in his first AB at Wrigley and the deafening standing ‘O’ it brought.

Jody Davis: “Jody, Jody Jody” was one of Harry Caray’s most memorable calls, and the Georgia born backstop was also quite the fan favorite. Two-time all star, gold glove winner and one of the MLB’s elite catchers of the 80s. Cool-ass moment: Pinch homer off Nolan Ryan in the Astrodome for a 1-0 Cub victory.

Matt Stairs: Given the unenviable task of replacing icon Mark Grace at first base, the Professional Hitter soon developed his own following for his throwback-softball style play.  Cool-ass moment:  Legend has it he ran the bases naked in practice, covered only in shaving cream.

Eric Karros: If over blown rookie Hee Sop Choi doesn’t get hurt in 03’, Jim Hendry doesn’t go get Karros, the Cubs don’t make the playoffs, and Steve Bartman would still exist in anonymity.  Cool-ass moment: His end of the season full page ad in the Chicago Tribune thanking Cub fans for a great season was a serious class act. 

Meanwhile, waiting in the wings….

THE TRIPLE – A of Cool

Kenny Lofton: If over rated weenie Corey Patterson doesn’t get hurt in 03’, Jim Hendry doesn’t go get Lofton, the Cubs don’t make the playoffs, and Steve Bartman would still exist in anonymity. Again.

Bob Dernier: Bobby D may be the Cubs finest leadoff man since the dead ball era, as he intimately understood AND executed the role.

Joe Wallis: The outfielder was a fan favorite that earned his nickname “Tarzan”, for his propensity of fearlessly diving headfirst after balls- and into a Holiday Inn swimming pool from the second floor balcony when in the minors.

Champ Summers: He didn’t do much as a Cub player but the burly chested bruiser’s tenure began fresh from a tour of duty in Viet Nam as a paratrooper, imagine that happening today.

Glen Allen Hill: There are many claims of the longest HR in Wrigley history but only Hill hit one that traveled across Waveland landed on the rooftop of a building on the fly. That along with his mammoth BP displays gets the gentle giant on the list.

Dwight Smith: Should have won rookie of the year over teammate Jerome Walton. A key spark-plug in the unlikely 89’ playoff run, plus he could croon the National Athem in tune!

Todd Walker: Not too many guys embraced being a Cub like Walker, even though he was inexplicably dissed and marginalized by manager Dusty Baker.

Micky Mornadini: The proto-typical second sacker was always money.

Willie Smith: Opening day walk off in 69 may be most prominent shot in modern Cub lore and gets sweet Willie a nod.

Dickie Noles: A true enforcer. Was on the team to basically throw at guys and keep the other squad honest. Always a raucous time when Noles pitched.

Chuck McElroy: The be-spectacled relief pitcher threw hard with control and could also hit… Great combination!

Carlos Zambrano: If he wasn’t such a knot head, Big Z would make the starting staff here. Had Cy Young potential, tossed a no hitter and won numerous silver sluggers for his sick switch hitting power.

Kerry Wood: It’s hard keeping kid K off the big league roster as for the first 5 years of his Cub career, he was one of the coolest ever. As of late however, all the fawning nonsense with his insufferable wife, may make him Mr. Metrosexual, but has dimmed his cool.

Jeff Samardjiza: The most recent Cub that rates is big Jeff. He has the firey personality and off the charts talent to be the iconic leader of a future dynasty. Why the current pinheads are dead set on getting rid of him should be troubling to any serious fan.

The Pine Brothers (77’ Cubs Bench: Larry Biitner et al) Manager Herman Franks secret weapon in a year where late inning comebacks were common. This philosophy of how to selflessly be a bench player lasted for a generation of Cubs teams that brought in savvy pros like Ken Henderson and Richie Hebner from successful winning programs to inject much needed gravitas. Something the current incarnation could desperately use.

So there it is. Perhaps some of your favorites were overlooked, and for that we apologize, but as in every subjective list, it’s well… subjective. A more difficult list might be the top un-coolest Cubs of all time, as the choices are almost infinite, with many of them on the current roster.

But never fear there’s hope for new blood. Tougher than nails lefty Travis Wood, phenom closer in waiting Neil Ramirez, and hot prospect Javier Baez all have the DNA to join the elite.

Stay tuned!