Chicago Cubs: Building my personal all-time best starting lineup

Here’s my take on a one game, winner-take-all ultimate Cubs starting lineup.

This is an exercise in futility along the lines of those All-Time NBA charts where you have a fictional $15 to spend on a starting five and the players are legends ranging from $1 up to $5. There is no right answer and while it’s an exercise in futility, it’s also an exercise in fun. And boy, don’t we need a little bit of light-heartedness right about now?

Given that I saw former Chicago Cubs hurler and current Marquee man Ryan Dempster’s recent starting lineup and took umbrage with selections, I decided I would make my own. Unlike Dempster, I never actually played with any of these guys, so I don’t have the need to include those I played with or won with – I’m just using his hypothetical sentiment that I need a lineup to win one game and one game only.

For ground rules for this little exercise, I’ll use the same ones Dempster used – an NL lineup complete with no DH, one reliever and one player off the bench. I think that’s fair and keeps things both interesting and appropriate for a Cubs squad.

Now, the one caveat I’ll throw out there is that I have no idea where this fantasy game will be played and I have no idea who is pitching for the other team. Not that it would matter for many of my picks, but depending on the handedness of the batters in the lineup or pitcher throwing against the Cubs in this dream matchup, it could alter or change my thinking.

Given that I don’t have that information at hand, I’m just gonna go with my gut in the same way that Dempster did and pick the guys I’d want going out for me if I got to play the role of David Ross and filled out the Cubs lineup card.

Chicago Cubs: A couple of current Cubs make the cut

Ya know, I’d really like to include a Damon Berryhill, Randy Hundley or even a David Ross. Heck, Jody Davis, Geovany Soto and Miguel Montero could even make their case! From a historical standpoint, Gabby Hartnett might even be the right choice. However, I never saw him play and I can’t say for sure if I’d want him out there against the imaginary flamethrower who will be toeing the rubber for the other squad.

Despite some defensive inadequacies compared to some of the other guys on the list, I think Willson Contreras has to be my guy. He’s got a cannon for an arm, is getting better as a receiver and he might just be the best hitting catcher to ever wear Cubbie blue (again, sorry Gabby – never saw you).

At first base, You’ve got three real choices – You could put post-shortstop Ernie Banks there to maximize your infield, you could go with the sweet-swinging greatest hitman of the 90s in Mark Grace or roll with incumbent present-day first-sacker Anthony Rizzo. Rizzo and Grace are both multiple Gold-Glove winners, while Banks is the greatest Cub ever.

When it comes down to it though, it’s probably better to slide Rizzo in at first base, as his ability to hit for power, choke and poke with two strikes and field his position make him a great asset in this ultimate lineup.

Chicago Cubs: Hall of Famers everywhere

At second base, there isn’t even a discussion as Ryne Sandberg makes this selection a no-brainer. A Hall of Famer and do-it-all keystone man, there’s no way he could be left off an ultimate Cubs team.

Since Banks isn’t playing first, that means he’s playing the position he came up as – a shortstop. Banks won back-to-back MVP awards as a shortstop – as well as a Gold Glove – and Mr. Cub makes the middle of this Cubs order formidable.

Third base was the toughest choice on the team – and for good reason. Third base for the Cubs is becoming a lot like middle linebacker for the Bears. Between Ron Santo, Aramis Ramirez and Kris Bryant, you have three guys who could easily slot in on just about any All-Star or all-time team.

All three have been known to pick it a bit at the hot corner, and while Santo is clearly the cream of the crop here, Ramirez was as clutch as they come both in the field and at the bat. And, all that Bryant has to show for his first five years in the bigs are some silly award trophies – namely: Rookie of the Year, MVP and World Series champion. That being said, Santo has to be the man at the hot corner, a fact our starting pitcher will surely enjoy.

Chicago Cubs: Hit ’em hard, hit ’em far!

While the infield had some contentious picks and choices, the outfield was pretty easy to deal with. In right field, you have none other than Sammy Sosa. Slammin’ Sammy was one of the most exciting and best performing players the Cubs have ever seen, and his bat was one of the most feared in all of baseball at the turn of the 21st century. The only player to put up three seasons of 60 or more home runs, Sosa belongs right in the heart of any Cubs all-time lineup.

While Hack Wilson would clearly be the offensive choice for center field, I went a different route. Nothing against the diminutive destroyer Wilson, but we have enough boppers in our lineup, and I know one guy who propelled the Cubs from the very top of the lineup with his “you go, we go” mentality.

No man knows how to work an at bat and grind down a pitcher to give his teammates a look at everything he’s got right off the bat like Dexter Fowler. Fowler may not be the 191-RBI man that Wilson was, but he’s a switch-hitter, a solid center fielder, proven winner and gritty catalyst atop a Cubs ultimate lineup that has no other man to hit leadoff (jeez – did these guys EVER have any other leadoff guy?).

In left field, there were plenty of nice options, such as Alfonso Soriano, George Bell or even a roving Hawk in Andre Dawson, who was really a right fielder (and darn good one for many years). That being said, sweet-swingin’ Billy Williams is the only choice here. Another left-hander to balance the lineup, Williams is one of the best players in Cubs history, and it’s no surprise his name and number hang on a flag high above Wrigley Field.

Chicago Cubs: How could you hand the ball to anyone else for one game?

This is going to be blasphemy to some and I’m going to be accused of recency bias, and I’m willing to take all the hits. But, for my money, for all the marbles, 2015 Jake Arrieta gets the ball over anyone not named Pedro Martinez.

The Cubs have had some of the best pitchers in the history of the game, some of whom I’ve seen throw baseballs and some I haven’t, but it just doen’t matter. The stuff, the swagger, the intensity, the attitude… and the wins. Arrieta sparked and then stoked the flames of those Cubs teams with his performance in the second half of 2015, becoming the best pitcher in baseball for the better part of two years.

His career as a whole, his longevity, and short years with the Cubs may not be quite the same as Fergie Jenkins, Mordecai Brown or even Greg Maddux, but he’s my choice. Jon Lester, Rick Sutcliffe and Kerry Wood would all be in the running if I didn’t witness firsthand what Arrieta was doing at the end of 2015. He was unhittable. His stuff was Pedro-esque. In addition, he was fearsome with the bat as well, offering pop and a threat out of the nine spot very few pitchers ever have.

That being said, the set up of this ultimate Cubs team allows me to pick another Cub. While some might go with Lee Smith, Dempster, Wood or even Carlos Marmol out of the pen, my vote is for Maddux. There was no better student of the game, and watching hitters deal with Arrieta for six or seven innings means he’d have all the adjustments figured out and know just how to attack guys whenever his name was called. He wasn’t phenomenal in the postseason, and he wasn’t a reliever, but the guy got more out of his stuff than anyone who ever threw off a rubber.

Chicago Cubs: What time is it? 3 am, of course.

Philosophy and strategy are important facets of both the modern game of baseball as well as “old school” thinking. I could have gone with the best hitter I didn’t put in my lineup and go with a guy like Grace, Dawson, Cap Anson, Derek Lee or Hack Wilson. It would certainly give me firepower to bring in off the bench in a crucial situation. However, none of these guys really pinch hit a ton because they were everyday players.

I could also go the defensive way and carry a guy like Jason Heyward, Javier Baez, Shawon Dunston, David Ross or even (sorry to say now) Addison Russell. Having one of these guys available off the bench to play Gold Glove-caliber defense would certain make the late innings tough for the other team.

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I could have even gone down a completely different road and carried a burner off the bench to put pressure on the defense and battery in the late innings when somebody gets on, a la Terrance Gore.

As a one game, do-or-die scenario though, I went a different route. I went with a guy who knows his role and can hit in the pinch better than just about anyone. A guy whose own manager nicknamed him “3 AM” because he claimed the guy could hit rolling out of bed at 3 am. Funny enough, hit is all he did when given a chance at a full time spot with the Angels last season. He’ll also be reunited with old skipper Joe Maddon should this 2020 season ever begin.

My last piece to the puzzle is, of course, Tommy La Stella. A guy who can work an at bat and get a hit in any situation, against any pitcher is a nice luxury off the bench, and La Stella is the single season leader in pinch hits in Cubs history (24 in 2018).

So, how would I put all these guys together and construct my lineup- click below: