The Rundown: Cubs Have Big Holes to Fill, Milwaukee Eyes World Series Sweep, Early Free Agent Predictions

“But every time I start to leave, they play another song. Then someone buys another round and whatever drinks are free…” – What Made Milwaukee Famous (Made a Loser Out of Me) by Rod Stewart

The Brewers are up 3-0 in the World Series and could clinch their first franchise championship tonight in Tampa. Amazingly, Milwaukee wasn’t much more than a ghost town last night. AmFam Field sold out its watch party, but bars in the Deer District and on Brady Street didn’t do that much more business than a regular Monday night. Yes, winning has become old hat in Cream City, and I say that without a hint of jealousy (lies!). I expect that most Milwaukee bars will be jam-packed this evening.

The 10-1 beatdown that the Brewers handed the Rays led to a heated discussion between me and a friend of mine. I received a text in the middle of the eight-run 5th inning that said “We’re going to have to take shit for a few years because Milwaukee is built to go on a run of championships.”

I won’t deny that the Brewers look unbeatable. They swept the Dodgers and could end the season with 11 wins in 12 postseason clashes against San Diego, Los Angeles, and Tampa Bay. They’re the best team in baseball right now in all facets of the game, full stop. That said, it feels a little bit like they caught the right teams at the right time, much like the 2005 White Sox or 2013 Red Sox if you’re looking for recent comparisons. Yes, the Dodgers won 100 regular season games and the Rays were victorious 98 times, but the Dodgers played in a division that had two bottom-five teams in all of baseball, and the Rays played in a league where two division winners would have missed the playoffs were they in the National League.

So let’s pump the brakes a little. The Brewers are a great team; there is no denying that, and flags fly forever. However, they haven’t really been challenged in the playoffs. The Cubs should be the class of the NL Central, but no team with a singular purpose to continually thread the needle should expect to be as dominant as Milwaukee is. And yes, Cubs fans will have to eat shovelfuls of shit until that changes. Unfortunately, nothing short of a front office makeover will change the way the North Siders do business. Those are the facts, and they are immutable.

With that in mind, let’s do a quick prep ahead of free agency, which could start as early as November 2. That’s a significant day on the North Side of Chicago, as it represents the 10-year anniversary of the Cubs’ 2016 championship. Jed Hoyer’s front office needs at least four starters, probably half a bullpen, two outfielders, a catcher, and at least one veteran bench player. Hoyer has about $100 million worth of wiggle room, but nothing in the way of strong trade assets.

In a vacuum, that sounds a lot like a rebuilding year, especially because the team’s best prospects — Josiah Hartshorn, Ethan Conrad, and Cade Townsend — are still a year away from making the team. Cade Horton will miss most of 2027, too, and nobody knows how good Justin Steele will be when he returns. The good news is that the Cubs could have a bona fide closer in Shelby Miller, but that may mean nothing more than a body to exchange for long-term assets at next year’s trade deadline. If Jaxon Wiggins is healthy, the Cubs may explore a deal for Reid Detmers or Mason Miller.

Long story short, Chicago simply lacks the pitching foundation, the pipeline of prospects we’ve been promised for over a decade, and the financial resources to challenge the Brewers next season. The Pirates may be a more formidable team than the Cubs in 2027, and a disaster awaits if Hoyer tries to fill every hole by Opening Day, whenever that may be. That means that the pitchers everyone covets, including Tarik Skubal, will probably sign elsewhere. If Hoyer just needed pitching, then yes, maybe he could swing for the fences this winter. Replacing Seiya Suzuki and Ian Happ is a bigger challenge with limited resources and a weak free agency class.

That means Hoyer will thread that ol’ needle once again, hoping to buy a year of prospect development while striving to win 85-90 games, if a full season is played. The Brewers should have an unfettered path to another NL Central crown while Hoyer and his staff try to reach a third consecutive Wild Card berth. Cubs fans, I’m sorry to report, are the middle children of perpetual subpar roster planning combined with too many injuries.

I hope I’m wrong. It would be nice to consistently write articles that are much more positive in nature.

Cubs News & Notes

• The Cubs have begun their security upgrades at Wrigley Field in advance of the 2027 All-Star Game.
• John Mallee removed himself from consideration to work as the Mets’ hitting coach to stay with the Cubs.
• Fielding Bible named the Cubs the top defensive team of the year. Pete Crow-Armstrong is their player of the year, and Alex Bregman was named their top third baseman.
• Patrick Mooney of The Athletic writes that Hoyer must be aggressive ($) the minute free agency starts.
• The Astros are expected to pursue starter Shōta Imanaga in free agency.
• Kevin Gausman put his Toronto-area home up for sale, which could mean a reunion with the Blue Jays is unlikely.
• The Yankees are expected to pursue veteran catcher Carson Kelly in free agency.
• The White Sox reportedly have their eyes on starter Clay Holmes, who holds a $12 million option with the Cubs. Holmes is looking at something like two years at $40 million or more.
• The Cubs are listed as the best possible landing spot for outfielder Steven Kwan. I was against this previously but Chicago could use his elite contact skills in its lineup.
• Owen Ayers is Chicago’s catcher of the future and he is closer to the bigs than you might think.
• Should we play Chicago Cubs Offseason Roulette? I’ll give you my picks, and you give me yours, deal? The Cubs retain Holmes and Matthew Boyd, trade for Detmers, and sign Freddy Peralta. I’ve got Happ going to the Reds, who desperately need outfield defense, Suzuki going to the Dodgers, Imanaga to the White Sox, and Gausman to the Braves.
• Additionally, Kwan to the Cubs seems like a decent pairing, though that would mean trusting right field to Matt Shaw. That would probably result in a reunion with Michael Conforto. I believe the Cubs will keep Kelly to catch. I’m okay if Miller (Shelby or Mason) becomes Chicago’s closer, but I’m not convinced Jacob Webb should stay.
• Finally, Hoyer will kick the tires on Skubal and Michael King but come up short. I’d love it if the Cubs traded Shaw and signed Conforto and Brandon Lowe. Keep your eyes on Foster Griffin, Sonny Gray, and Sean Newcomb.

Ball Four

This is one of the coolest cross promotions I’ve seen.

World Series News & Notes

Milwaukee is turning back the clock while simultaneously moving baseball forward.

The Brewers scored all eight of their 5th inning runs with two outs. That is a World Series record. The inning featured seven consecutive Brewers hits, from William Contreras through Jackson Chourio. The Brewers became the first team to notch seven consecutive hits in any postseason game, per STATS.

Brandon Woodruff pitched the 9th inning and recorded the game’s final out. He hasn’t pitched since July 4 and was a surprise addition to the roster.

Peralta’s stellar postseason run came to a crashing halt in last night’s loss.

Griffin Jax will take the mound for the Rays tonight to avoid the sweep. The Brewers did not name a starter.

Tuesday Stove

Jim Bowden of The Athletic dropped his 2026-27 free agent predictions ($). He sees the White Sox as a fit for Skubal on a $350-$500 million deal. Wowsers.

The Astros released former Cubs prospect Nelson Velázquez.

Francisco Lindor will be honored as this year’s recipient of the Roberto Clemente Award.

The league is testing restricted outfield shifts in the Arizona Fall League as a way to increase scoring. Is it too late to send Shaw to the AFL? That has disaster written all over it otherwise.

Three from the Bill Chuck Files

1. The Brewers have won 49 games in the regular and postseason in which they’ve trailed.
2. Milwaukee is the first team in MLB history to win seven of their first eight postseason games after trailing.
3. The Royals were the league’s first choice to join the NL Central when MLB went to two 15-team leagues in 1998. They declined, so the Brewers shifted over from the AL Central.

Try to imagine baseball with Kansas City in the NL Central instead of Milwaukee, starting with the Sammy Sosa – Mark McGwire years up until the present day.

Apropos of Nothing

Remember when the Cubs won 20 of 23 and we thought they’d still be playing at the end of October? Those were some fun times.

Return to Sender

The Brewers have won eight straight against the Padres, Dodgers, and Rays by a combined score of 39-17. Ex-Cub Daniel Vogelbach is Milwaukee’s hitting coach.

Extra Innings

The arguments for realignment are always self-serving to the author, but putting the Cubs in the AL East is extreme bias. Here’s my issue with the linked idea: You can’t cry “small market” when three of baseball’s final four teams are at the bottom in payroll. Have fun with it anyway.

They Said It

• “Catchers have to process more information than anybody on the roster. You’ve just got to keep hearing it and hearing it, so you can implement things faster, whether it be scouting reports or signs from the bench during the game. We’re just trying to start that process with Owen [Ayers]. – Craig Counsell
• At some point, for a young catcher in a Major League game, it goes fast, because they’re like, ‘Oh my god, I’ve got to make a pitch call. I’ve got to pick up a sign for a throw over. I’ve got to block a ball. I’ve got a baserunner that might steal.’ It just goes fast, so we’re trying to start that process to slow him down.” – Counsell
• “We’ll make the best [free agent] decisions with the information we have at the time. Some of those may come before December 1st, and some may come after, but I don’t think anyone at this point has a firm grasp on that. I think if they say they do, they’re probably incorrect. I think we’re all going to have to make certain assumptions.” – Hoyer

Tuesday Walk-Up Song

Who knew Tom Petty was the king of Milwaukee?