Like many baseball fans, I’ve looked forward to projecting Opening Day rosters since I was a young kid. I’ve maintained a tried and true method: 25 names written on paper (always), ink pen for the sure’s and pencil for the maybe’s, from 1B around the horn, through the OF, and back to C. 5 starting pitchers, plus a bench and bullpen. As I became more advanced and eloquent as a baseball fan (around age 10), I began penciling in possible replacements, aka the top names at AAA. This method served me well for decades, and I still have several old binders that I occasionally look back on with fondness to see my thought process heading into the 1986 or 1996 or 2002 seasons.

Things have changed over the past decade or so. I’ve had to reluctantly shorten my bench and add to the bullpen. Some pitchers have been added as swingmen, and certain bench players have adopted the UT label rather than my traditional IF or OF. This season was going to further test my conventional leanings with the addition of a 26th man. I was nearly ready to break my trusty black Bic and faithful yellow #2 when things really got weird…

2020 happened.

A WHOLE NEW GAME

2020 was already set to introduce several changes to the traditional roster construction, with the addition of a 26th player as well as a limit of 13 pitchers, the official title of “two-way” players, and limitations on when position players would be allowed to pitch in a game. There are/were several other rule changes adopted over the past offseason, but for the purposes of this discussion, I’ll try to stick to the roster rules. The 13-pitcher max rule, as well as the “two-way” player designation and restrictions on when position players are allowed to pitch, have all been scrapped for this season.

It would take an entire article to describe all the unique roster regulations for this season, and as much of a baseball nerd as I am, I’d much rather just link to this breakdown here at MLB. I will point out some key factors to keep in mind.

• The rules regarding the 40-man roster remain mostly intact. Players can be moved on and off this list as usual.
• Teams are required to submit a 60-player max “player pool”, meaning those who would be eligible to play this season. Players on this list who are not on the active roster will train at Alternate Training Sites (South Bend for the Cubs).
• Obviously, not all 60 players will be members of the official 40-man roster, but any player added to the active roster throughout the season will be required to be added to the 40-man roster prior to eligibility.
• Any player removed from the 60-man Player Pool cannot be reinstated to the same team this year. Those players can be added to other team’s rosters, allowing for some trade flexibility.
• All teams are required to maintain a 3-man “taxi squad”, one of which has to be a catcher. These players will travel with the team on road trips, and return to the Alternate Training Site during homestands. The catcher, however, will remain with the ML team to serve as the bullpen catcher.
• The purpose of this taxi squad is to eliminate commercial air travel in the event of a player testing positive for Covid-19 and needing a replacement. Players on the 3-man taxi squad are not required to be on the 40-man roster, but would need to be added before being eligible to play on the active roster.
• Initial active rosters will be capped at 30 players. I say capped because that’s not a requirement, but I don’t see any reason teams would carry less. Rosters will be pared down to 28 players two weeks after Opening Day, and down to 26 players two weeks after that.

I could go on, but nah. That’s most of what we need to know to get to the good stuff.

THE THOUGHT PROCESS

I’m going to be completely honest here and admit I am not as in tune to what is happening as I would normally want to be to feel comfortable writing a predictive piece. These past several months have done that to everyone in one form or another. But like everything else in these uncertain times, we have to persevere through the uncertainty. I’ll put my thoughts on record, and feel free to make fun of me if (when) I miss two or ten.

Sports bring out strong emotions, and I’m certainly not immune to the hot take. I’ve never consumed much talk radio, but I am aware the louder and more ignorantly one yells on that platform the more attention one receives. I am, however, somewhat active on Twitter, which is far worse.

I say this not to ask for sympathy, but to assure you I try to obtain my information from more legitimate sources.

Theo has had several interviews discussing possible roster configuration, and his insights are both telling and somewhat obvious. You don’t want a young prospect sitting at home with no minor league season, but you also don’t want him sitting on a ML bench without playing time. As much as we want to see Brennen Davis, Miguel Amaya, and Christopher Morel playing at Wrigley, it’s not going to happen without a catastrophic series of events.

Theo has said that the top prospects will remain in South Bend to continue their development. Any fringe players carried on the active MLB roster will likely be those who can serve a specific role, while providing versatility if possible, without worrying about hindering their future development. Think AAAA players who may have use to win a game but without much upside. This seems fairly obvious, and certainly plays on my thoughts in selecting those last few roster spots.

I’ve been very intrigued by how Boss Ross would handle being the boss. I’ve thought that since he is not far removed from his playing days he would more easily relate to the daily mental grind the players endure, and may be more sympathetic to a routine than Maddon was. I think he’ll produce a more structured and consistent lineup, while also demanding accountability for production while understanding that certain players shouldn’t play in certain situations.

The biggest influence I’ve felt Ross would have, however, is his handling of the pitching staff. That’s his gig. The analytical analysis of his career playing stats pale in comparison to his reputation as a handler and even de facto coach of a pitching staff.

Ross has said that, if it’s up to him, he would prefer to go initially with 14 position players and 16 (!) pitchers on the Opening Day roster. As much as that shocks my traditional sensibilities, it also makes a lot of sense. I haven’t seen confirmation from the front office, but that’s the template I’m going to work with.

THE POSITION PLAYERS

There are many here that are obvious, so I’ll just get them out of the way without much drama. I think this is our generic starting lineup:

• 1B: Anthony Rizzo (bats L)
• 2B: Nico Hoerner (R)
• SS: El Mago (R)
• 3B: Kris Bryant (R)
• LF: Kyle Schwarber (L)
• CF: Ian Happ (B)
• RF: Jason Heyward (L)
• C: Willson Contreras (R)

I feel there are also some fairly safe picks on the bench, which will of course also be used in platoon situations and to carry on the tradition in that other league of part-time baseball players:

• C: Victor Caratini (B)
• IF: Jason Kipnis (L)
• IF: David Bote (R)
• OF: Steven Souza, Jr. (R)
• OF: Albert Almora, Jr. (R)

If we go by Ross’s wish of 14 position players on the initial roster, we have one spot open. There are three players I see as having a legitimate shot.

Left-handed hitter Daniel Descalso is highly respected for his leadership abilities and clubhouse presence, but his performance and lack of versatility hinder his chances at a spot on the Opening Day roster. In fact, my guess is he is removed from the 40-man to open a roster spot.

Switch-hitter Robel Garcia is another option. He’s been a feel-good story, but like Descalso, I just feel that the Cubs have his potential skill set covered. Javy has SS, with Nico as a backup. 2B is covered by no less than four players likely to make the roster, and we seem to have some pop off the bench with a good balance of lefties and righties. Like Descalso, I can see Garcia being removed from the 40-man if a roster crunch arises, though I think he holds his spot longer than Daniel does.

That leaves my pick for the last position player slot:

• OF: Ian Miller (L)

I believe Miller fills a couple roles necessary to win a particular game or two, in addition to being just old enough (relatively) and without enough upside to be concerned about hindering his development. He can play all the outfield spots well, and can steal a base in a tight situation. I think he makes the initial cut, but will need to be added to the 40-man. Whether he survives the culling of the roster over time is anyone’s guess. I hope his performance demands it.

THE PITCHING STAFF

Like the starting lineup, there isn’t much drama in the starting staff, with a couple notable asterisks. Jose Quintana has been throwing after receiving stitches on a finger on his throwing hand following a dishwashing incident, and is on the IL. He is expected to miss at least the first couple weeks of this abbreviated season.

Alec Mills has been tapped to take Q’s spot in the rotation. That was expected. What wasn’t expected, and something I have not been able to confirm, is a statement from Ross that Lester is slated to enter the season as the #4 starter.

I don’t put much stock in #1-#5 slots, as they always change throughout the season and even based on usage and matchups. I just don’t know why Ross would say that, if for nothing else but a PR backlash. I haven’t heard that Lester has been bad. In fact, I’ve heard he is in incredible shape and looked very good. Maybe Chatwood looks incredible? We can hope!

Anyway, Hendricks has been announced as the Opening Day starter, an honor I completely agree with. So with that in mind, the starters:

• R Kyle Hendricks
• R Yu Darvish
• R Tyler Chatwood
• L Big Jon Lester
• R Alec Mills

So now we get to the pen, where things begin to get crazy. I’ll just start off here with a little trivia nugget I saw the other day:

As far as Cubs bullpen experience goes, could you guess who currently holds the title as most tenured pen arm?

That would be Kyle Ryan, who was called up on 4/16/2019. Chatwood is now listed as a starter. Let that insane amount of turnover sink in for a minute or two. No one even remotely associated with the Championship team is left in the pen.

Further following Ross’s wishes, we have to create an 11-man bullpen. That is not a misprint. We have to construct an 11-man bullpen. Seriously, I’m not kidding. An 11-man bullpen. Welcome to 2020.

Oh, heck, let’s start with the probables:

• R Craig Kimbrel
• R Jeremy Jeffress
• R Rowan Wick
• R Duane Underwood, Jr.
• L Kyle Ryan
• L Brad Wieck

You know most of these guys, either through reputation, Michael’s development updates, or both. As much promise as there are question marks, especially at the top end. I will say I have heard very good things about Underwood, Jr. He’s been sitting a tick higher out of the pen, 94-96mph, but the big news is his development of the Cubs’ soon-to-be-patented knuckle-curve.

I don’t know if that is all due to Kimbrel or the pitching lab, but the proliferation of this particular pitch throughout the Cubs’ system may very well be Kimbrel’s lasting legacy for his time with the Cubs.

A few others who probably make the initial cut:

• R James Norwood
• R Dan Winkler
• R Ryan Tepera

Why not? Have I mentioned we have to build an 11-man bullpen? This is how you fill out an 11-man bullpen.

So, if I’m right (and I’m not, but even so), that leaves 2 spots. These 2 spots are the most nonsensical and unpredictable of any on the roster. What immediately sticks out to me is the lack of lefty arms, especially those that can miss bats in a critical situation. Rex Brothers fits that bill immediately, though I believe he would also need to be added to the 40-man.

I feel the reason Ross wants to overload the roster with pitchers is because the starters aren’t properly stretched out to begin the season. He will likely go easy on the main guys, which will require more depth, and possibly guys who can throw multiple innings. That’s where players like Jharel Cotton and possibly even Colin Rea could get a look.

As always, Adbert Alzolay looms large, but for his health. He could be a complete non-factor or a season savior out of the pen in crucial situations. Same with Dillon Maples and even Dakota Mekkes. It’s 2020, why not?

If we really want to get crazy, we can dream on 2nd-rounder Burl Carraway, who was just added to the 60-man Player Pool. His 100 mph fastball and absolute hammer curve from the left side would look really good if he can harness his control, which most observers believe he can do when he gets into a professional program. I believe Carraway is going to be our greatest homegrown reliever since Lee Smith, and I think he will make his debut and an impact in 2020, but not on the Opening Day roster.

So, we have two pen spots left. The two most volatile and subjective spots on the team. The only credible opinions on who will secure these final two spots of an 11-man (!!!) pen are those who have seen them throw and know who is in the right state physically and mentally.

That isn’t me, so I have to guess.

I really think Ross wants some arms to go multiple innings so he can go easy with the starting staff the first time or two through the rotation, but he has an 11-man (!!!!!!!) bullpen at his disposal. I think we go with what we know.

• L Rex Brothers
• R Dillon Maples

That equals 30, right?

AND THE REST

There needs to be a 3-man “taxi squad” traveling with the team. One of these players has to be a catcher.

This taxi squad is assumed to be a catcher, position player, and a pitcher. The purpose is to avoid air travel if a team needs to make a transaction while on a road trip. These taxi squad players do not have to be on the 40-man roster, but would need to be placed on it to replace an injured or Covid-19 positive player on the active roster.

Josh Phegley will likely fill the role of taxi squad catcher. He will not be on the 40-man. Whoever survives the 40-man cut between Descalso and Garcia could be the position player, or I could see someone like Zagunis traveling around, just because.

Your guess is as good as mine on the taxi squad pitcher. It’s likely to be a rotating role, with the possibility of getting the “big-league” travelling experience and the major league scouting and coaching structure more of a draw than the possibility of actual game action.

ONE FINAL WISH

I often end my nonsensical ramblings with a well-placed (in my mind) musical lyric.

As we head into this crazy season of whacked-out baseball in these most trying of times, there is something I’d love to hear much more than any rhyme from Mick, Paul, or even Bob.

I’d love to see a comment from TC.

GO CUBS!