This is quite the road trip for the Cubs, who have not played many games against NL Central opponents this season.

First, Craig Counsell and Co. head to St. Louis for a 3-game set before the new Cubs manager returns to Milwaukee for the first time on the other side of the rivalry.

Counsell spent 9 seasons at the helm of the Brewers, managing 1,351 games between the regular season and the playoffs. He also spent 6 seasons in Milwaukee as a player and another 3 years as a front office executive prior to becoming a manager.

It’s an important road trip for the Cubs in that they’ll be squaring off against the team directly behind them in the standings (Cardinals) and the squad ahead of them in 1st place in the division (Brewers).

Pitching probables

St. Louis

Friday: LHP Shota Imanaga vs. RHP Miles Mikolas
Saturday: RHP Jameson Taillon vs. TBD
Sunday: TBD vs. RHP Sonny Gray

Both teams currently have only 4 members in the starting rotation, which leaves some wiggle room for bullpen games or new starters to enter the mix.

From the Cubs’ perspective, they gave Ben Brown the start Thursday in the homestand finale against the Braves with Kyle Hendricks now moved to the bullpen. They characterized it as a “bullpen day” and it appears as if Sunday could be a similar type of game.

Sunday represents Javier Assad’s normal turn in the rotation, but the Cubs could opt to push him back a day and start the series opener against the Brewers in Milwaukee.

The reasons for that are twofold: to manage Assad’s innings during a stellar season and also to roll out the best pitchers against the team the Cubs are chasing in the division (Brewers).

If Assad does pitch on Monday, the rotation looks as follows for that all-important 4-game series:

Milwaukee

Monday: RHP Javier Assad vs. RHP Freddy Peralta
Tuesday: LHP Justin Steele vs. RHP Tobias Myers
Wednesday: LHP Shota Imanaga vs. RHP Bryse Wilson
Thursday: RHP Jameson Taillon vs. RHP Colin Rea

Of course, the Cubs could make changes to this rotation in the coming days. They have been aggressive this season in ways to keep their rotation fresh and they also have had plenty of injuries to work around.

Assad threw 124 innings last season between the majors and minors and his career high is 146 innings in 2022. He is on pace for more than 170 innings this season, so the Cubs will be cognizant of his workload as the year progresses.

They’ll find ways to maximize Assad’s matchups, as he has been phenomenal this season (1.70 ERA).

The Cubs rotation as a whole has been on fire. In the last 27 games dating back to April 23, a Cubs starter has allowed 3 earned runs or less in 23 of those games.

Led by Shota Imanaga, the Cubs starting staff has been a major strength of the team over the last month.

Quote of the Week

“If I’m being honest, I haven’t really walked around too much. I’ve been going from the field back to my house. The only time I really go out anywhere is buying my latte at Dunkin Donuts. Hopefully, I can keep doing well and keep putting up stats, so people recognize me while I’m walking around.” — Shota Imanaga said through interpreter Edwin Stanberry about his interactions with Cubs fans in Chicago.

Storylines to keep an eye on

—The standings become a common point of discussion in baseball consistently starting around Memorial Day. The Cubs are hovering around 1st place but have been looking up at the Brewers for the last few weeks. This is a pivotal road trip and the 4-game set in Milwaukee is easily the biggest series of the season to date.

—Drew Smyly is expected to return while the Cubs are in Milwaukee, though the exact date is uncertain at the start of the road trip. He will provide another solid veteran arm in a bullpen that has been hit hard with injuries over the past few weeks.