Cubs vs. Cubs: Drafting a pair of all-time teams

CHICAGO -- With no live Cubs games, we thought we'd fill the void by debating the ultimate Cubs game: a matchup between two teams composed of some of the greatest players in franchise history. To help pick these (totally hypothetical) teams, we've enlisted Cubs broadcaster Len Kasper. There’s no actual game to be played, but let’s pass the time by discussing and appreciating some of the franchise’s all-time greats.

Jordan Bastian (MLB.com Cubs beat reporter): Thanks for doing this, Len. Before we begin, let’s establish the ground rules. For this sandlot-inspired all-time draft, we’re going to stick with the Modern Era, so since 1900. Eligible players had to have spent at least parts of three seasons with the Cubs. That helps avoid any one-year-wonder ringers.

We’ll pick nine position players, including a designated hitter, for each lineup. We’ll also have a slot for one bench/utility guy. Hey, if we get to the local park and someone gets hurt, we’ll need someone to replace them. Or maybe that bench player can fill a late-game role.

For the pitching staff, let’s go with one starting pitcher and two relievers. That’s it. That brings the players drafted up to 13 apiece. The idea here is that you’re drafting the player at their peak level from within their Cubs years.

At the end, we will also select a manager. And because it’d be difficult to simulate this one, I’ve enlisted an analyst from a rival Major League club to examine our rosters and give his take on who would win this dream game.

Are you ready? I’ll give you the honors of selecting first.

With the No. 1 pick, Team Kasper selects: Hack Wilson, CF
Kasper: Having the first overall pick, I had to go with a clear No. 1 guy at a more "shallow" position. Center field was the obvious category, and Wilson the no-brainer pick. His 1930 season was astonishing -- 56 home runs, 191 RBIs (an all-time single-season record), 105 walks and a .723 slugging percentage.

With the No. 2 pick, Team Bastian selects: Ernie Banks, SS
Bastian: Man, I expected some strategic picks, but I didn’t expect it right out of the chute. That’s a great pick and definitely leaves me scrambling in center. I’ll put that off until later. For my top pick, I’ve got to go with Mr. Cub himself at shortstop. In his consecutive National League MVP seasons in 1958 and '59, he slugged .605 and averaged 46 homers and 136 RBIs while playing plus defense. I want him anchoring my lineup and defense.

With the No. 3 pick, Team Kasper selects: Rogers Hornsby, 2B
Kasper: Well, because you grabbed Banks (which was a no-brainer No. 2 pick), I had to grab Hornsby. He’s arguably the greatest right-handed hitter of all time not named Mike Trout. I’m really digging a lifetime .358/.434/.577 slash line.

With the No. 4 pick, Team Bastian selects: Sammy Sosa, RF
Bastian: Wow, Hornsby is another fantastic pick. I had him atop my second-base chart, but like with Wilson, I didn’t anticipate you’d grab him so fast! He wasn’t with the Cubs long, but he meets the criteria. And can we talk about the 10.4 WAR in 1929? Sheesh. OK, but about my pick ...

I’m taking Slammin’ Sammy here. I was a ‘90s kid, and I remember we had to stop what we were doing to watch his at-bats. I feel like he homered every time I went to Wrigley Field. There is controversy over his career numbers, yes, but for this exercise, I’ll take 1998-2001 peak Sosa and the 243 homers he hit over that four-year span.

With the No. 5 pick, Team Kasper selects: Billy Williams, LF
Kasper: I’m really happy to get Sweet Swingin’ Billy here and really needed a left-handed presence in my lineup. He hit 426 career homers. Enough said.

With the No. 6 pick, Team Bastian selects: Gabby Hartnett, C
Bastian: You tackled center field right away. Another position where the depth thins out quickly is behind the plate. With that in mind, I’ll snag the obvious top choice in Hartnett. He could mash and was a tough out, and the Hall of Famer was a rock for those 1930s teams that made multiple World Series.

With the No. 7 pick, Team Kasper selects: Bruce Sutter, RP
Kasper: I’m going to go a bit rogue and dip into the pitching department early. I’m grabbing Sutter because there were two clear top relievers available -- Sutter and Lee Smith -- and I didn't want to make a "defensive" pick later, if you grabbed one early. Sutter led his league in saves five times.

With the No. 8 pick, Team Bastian selects: Kerry Wood, SP
Bastian: OK, I’ll admit, I’ve watched Wood’s 20-strikeout game from 1998 twice while we’ve been staying at home. And I think this pick might be influenced by all those insane curveballs I’ve watched over and over. But if we are playing one sandlot-style game, I want Kid K on the mound to rack up strikeouts. There are better pitchers from earlier eras, but I think Wood’s stuff in his prime would play in any era. Sure, he walked guys -- that’s the risk -- but I’ll take that near 30-percent strikeout rate over his first five Major League seasons.

With the No. 9 pick, Team Kasper selects: Kris Bryant, 3B
Kasper: I’m pretty happy I’m able to get KB with the ninth pick. So many good choices at third base, but I think he's one of the better overall players in team history. So I had to take him here. Five years in, he's won just about every award imaginable already.

With the No. 10 pick, Team Bastian selects: Anthony Rizzo, 1B
Bastian: We can’t separate Bryzzo, right? If you’re going with Bryant at nine, I’ll take Rizzo at 10. And there is an argument to be made that Rizzo is on his way to being considered the best first baseman in Cubs history. He hits for power, gets on base and plays Gold Glove defense. And as the Cubs’ all-time leader in hit-by-pitches, maybe he’ll just take one for the team to set up a rally. Warn your pitchers.

With the No. 11 pick, Team Kasper selects: Derrek Lee, 1B
Kasper: This is a sentimental pick, I’ll admit. He's one of my favorite all-time guys and players, but make no mistake, he deserves to be taken this high. His 2005 season was one to behold. He had an NL-leading 199 hits, 50 doubles, .335 average and 1.080 OPS.

With the No. 12 pick, Team Bastian selects: Ryne Sandberg, 2B
Bastian: You know, Mark Grace works at Marquee Sports Network with you now. I hope he’ll be OK with you passing him up to play first base! For my pick, I feel like we owe Sandberg -- one of the greatest Cubs of all time -- an apology for waiting this long to call his name. He was my favorite player as a kid, and in his prime, he could hit for power, run and play clean defense. Ryno is manning second for Team Bastian.

With the No. 13 pick, Team Kasper selects: Andre Dawson, RF
Kasper: Wow. I’m thrilled Dawson was still available at No. 13. My outfield of Williams-Wilson-Dawson is pretty jaw-dropping, if I do say so myself. Hawk's finest season came in 1987, when he won NL MVP (.287 average, 49 homers and 137 RBIs).

With the No. 14 pick, Team Bastian selects: Ron Santo, 3B
Bastian: Yeah, that’s a dynamic outfield, but I’ll take my infield of Rizzo, Sandberg, Banks and Santo. Good luck getting a grounder through to the outfield. Santo won five Gold Gloves and adds another Hall of Famer to my lineup. And can I have him in the booth calling this game when he’s not on the field?

With the No. 15 pick, Team Kasper selects: Jake Arrieta, SP
Kasper: I'd put 2015 Arrieta up against any starter in history: 22-6 with a 1.77 ERA.

With the No. 16 pick, Team Bastian selects: Mark Grace, DH
Bastian: That pick makes me have second thoughts about selecting Wood when I did. I don’t think I needed to move on him so early. Arrieta is an amazing pick for this one-day dream game. But there’s no looking back now. We could have a lot of strikeouts on the mound, so I am focusing on trying to build a lineup that can put the ball in play. So if you’re not going to take Grace, I will. I want his contact-oriented, doubles-churning bat protecting the heart of my lineup. I’ll let him and Rizzo decide who plays first and who slots in as the DH.

With the No. 17 pick, Team Kasper selects: Lee Smith, RP
Kasper: Again, with depth being an issue at reliever, the thought of having both Sutter and Smith is too good to pass up. Easy choice here with 478 saves under this Hall of Famer's belt.

With the No. 18 pick, Team Bastian selects: Alfonso Soriano, LF
Bastian: Yeah, I really need a good day out of my lineup against your pitching staff. And now, we’re also getting into the territory where the early dominos are exposing depth issues. There are a lot of ways to go at left field with Williams off the board. I’ll take Soriano, whose 2007-08 peak with the Cubs was really strong. He could still hit for power (.547 slugging percentage in those two years) and run.

With the No. 19 pick, Team Kasper selects: Stan Hack, UTIL
Kasper: I want to make sure the early 20th century Cubs are well-represented, because there were some terrific players who were on some great Cubs teams. Hack was no slouch (and his lefty bat on my bench is a nice side benefit). I might be playing with fire here, but in 16 years (all with the Cubs), Hack slashed .301/.394/.397.

With the No. 20 pick, Team Bastian selects: Javier Báez, UTIL
Bastian: Hack is really underappreciated. I love that pick. But I’m not sure you’re going to love my pick in the same way here. I’m taking Báez here as my utility man off the bench. First and foremost, I want El Mago on my roster to possibly create something late. Maybe he enters and steals a base. Maybe he scores with an incredible slide. If someone gets hurt, he can essentially play any position on the diamond. Or, hey, maybe I bring him in late and he slugs a homer. I just like all the possibilities that exist. And as a benefit, I think this probably robs you of who you had in mind for shortstop.

With the No. 21 pick, Team Kasper selects: Shawon Dunston, SS
Kasper: Shawon, if you're reading this, I am thrilled you're on my team. But to not grab Báez before Jordan could swoop in and steal him away is my only regret with this draft. If I had a do-over, I'd take Báez at No. 15 and Arrieta at No. 21. Once Jordan picked Wood, Arrieta was essentially available for the rest of the draft. Arrieta clearly deserved to be taken that high, but I risked losing another player I really needed/wanted. Having said all that, late-1980s Dunston (an All-Star in both 1988 and '90) flashed some great leather at short and could steal a bag as well (212 career stolen bases).

With the No. 22 pick, Team Bastian selects: Carlos Mármol, RP
Bastian: My regret to this point is how I built (or did not build, to be more accurate) my bullpen. I have been so focused on my lineup that it’s an area I overlooked. But even without the Hall of Fame duo of Sutter and Smith available, I can still find a way to miss bats. And there’s no better alternative left than Mármol. Specifically, I’m thinking of the 2007-08 version that had a 2.13 ERA, 216 ERA+, .150 opponents’ average and a 33.2 percent strikeout rate. The righty’s rate of 11.7 strikeouts per nine innings remains the best career mark in Cubs history.

With the No. 23 pick, Team Kasper selects: Bill Madlock, DH
Kasper: The two choices here were Madlock and Aramis Ramirez. I’m choosing Madlock mainly because I felt like I already had a bevy of middle-order guys and wanted to have a hit machine in my lineup. Mad Dog won four NL batting titles, including back-to-back crowns as a Cub (.354 in 1975 and .339 in '76). The dude could rake.

With the No. 24 pick, Team Bastian selects: Paul Assenmacher, RP
Bastian: Madlock is tied for the highest career average in Cubs history with a .336 mark. Strong late-round pick there, Len. OK, hear me out on this pick. You have a right-handed-heavy lineup, but you’ve got Sweet Swingin’ Billy Williams in the middle and then a tough out in Stan Hack on your bench. I want a lefty available for a late-game matchup. That led me to Assenmacher. I’m thinking of the 1990 and '91 seasons, when he had a combined opponents' slash line of .200/.254/.271, with a 28-percent strikeout rate against lefties. Are we using a three-batter minimum rule? Hopefully Wood and Mármol can carry a heavy load for me.

With the No. 25 pick, Team Kasper selects: Willson Contreras, C
Kasper: With Hartnett gone early, I knew Contreras was my guy and could wait to take him. I wish I had contemplated the same thing with Wood and Arrieta, but bygones are bygones. Contreras is one of the elite catchers in the game today and is coming off a .272/.355/.533 2019 season.

With the No. 26 pick, Team Bastian selects: Rick Monday, CF
Bastian: It’s only fitting that we end where we began, with center field. That smart pick right out of the gates gave me all draft to consider my option for center. Shoot, can I ask Báez to play center? Sosa played some in his career. No, I’ll take Monday. He had a respectable Cubs career (.270/.366/.460). I like adding another lefty bat to the mix for balance and the fact that he can draw a walk as the top of the lineup comes around again.

OK, Len, it’s time to pick our managers.

Team Kasper manager: Joe Maddon
Kasper: The two options here for my money were Frank Chance, who won 100 games as player-manager in the early 1900s, and Joe Maddon, who led the Cubs to their first World Series title since the Chance-managed 1908 club. Recency bias won out, and I'm proud to have Maddon be the architect of this great club.

Team Bastian manager: Jim Frey
Bastian: You aren’t wrong about the top two choices. I also have a fondness for the Don Zimmer years from my childhood. But I’m going to go the sentimental route with Maddon off the board. I’ll take Frey, who died on April 12. He helped lead the 1984 Cubs to the NL Championship Series and played a key role in teaching Sandberg to unlock his power potential. With Ryno probably batting second for me, I’ll take Frey in the dugout.

So, what’s your lineup going to look like?

Team Kasper
1) Hornsby, 2B
2) Bryant, 3B
3) Williams, LF
4) Wilson, CF
5) Lee, 1B
6) Madlock, DH
7) Dawson, RF
8) Contreras, C
9) Dunston, SS

Kasper: That's a pretty good lineup. Just consider the career on-base percentages of Nos. 1-6: .434, .385, .361, .395, .365 and .365. My No. 7 hitter cranked 438 homers and compiled nearly 2,800 hits. Not bad! On my bench, I have Hack, who could take a late-inning at-bat for Dunston, if needed.

How about yours?

Team Bastian
1) Rizzo, 1B
2) Sandberg, 2B
3) Sosa, RF
4) Banks, SS
5) Grace, DH
6) Santo, 3B
7) Hartnett, C
8) Monday, CF
9) Soriano, LF

Bastian: The running joke is that Rizzo is the greatest leadoff hitter of all time, but there are small-sample numbers to back it up. His career 1.028 OPS in the No. 1 spot is the highest in MLB history (min. 200 plate appearances). So Rizzo will set the table. I like Grace in the protection slot and the overall balance, and I think my team can put the ball in play enough to counter your awesome pitching.

Kasper: Yeah, your lineup is pretty formidable with good left-right balance. But if Arrieta is on his game, platoon advantages are pretty moot.

Bastian: Maybe, but let’s have someone else make that call.

Rival MLB front office analyst's take

Hitting: Advantage Jordan. While the top four of Len’s lineup is bound to post a lot of first-inning crooked numbers, the balance achieved in Jordan’s lineup gives him the advantage.

Baserunning: Advantage Len. The stolen bases at the bottom of Len’s lineup (from Lee, Madlock, Dawson, and Dunston) will help make up for the lack of thump down there.

Defense: Advantage Jordan. It may be boring, but this is the most lopsided difference between these two teams in my eyes. Jordan has constructed an all-world defensive infield.

Starting Pitching: Advantage Len. You could have players from all 30 franchises available and it would be tough to stack up against the two-year run Arrieta posted for the Cubs from 2014-15.

Relief Pitching: Advantage Len. Two throwback Hall of Fame firemen here, including Sutter, who was putting up big strikeout rates out of the bullpen before it was cool.

Overall: Even though I gave Len three wins to Jordan’s two here, I give Jordan the overall nod. His massive edge in defense helps make up the difference in pitching, and the balance and versatility throughout the rest of his roster makes him the winner in my eyes.