The Rundown: Cubs Trade Speculation Escalates, Kwan Checks Several Boxes, Banner Heads to Orioles, Rays Win AL Pennant

“Why not think about the times to come?” – Don’t Stop by Fleetwood Mac

I don’t know what’s in the water, but Bryce Harper seems to be a hot topic as far as the Cubs’ future outfield is concerned, and I don’t know why. Harper has a full no-trade clause, and though his contract is not too prohibitive to move (5 years/$125.7 million), the Phillies’ window of contention is still very much wide open. Chicago, on the other hand, has nothing but prospects and Matt Shaw to offer in trade, and neither will interest Dave Dombrowski or Preston Mattingly. Harper is also on the wrong side of 30 and may not offer enough production to replace Seiya Suzuki. I never thought I’d write that, but it’s true.

Though Suzuki and Ian Happ are free agents, who replaces them won’t matter unless Jed Hoyer can field a rotation that is good enough to unseat the Brewers. Harper is a fun name, but Hoyer should be thinking about Tarik Skubal, Reid Detmers, and Freddy Peralta instead. Justin Steele is far from a sure bet, Cade Horton is looking at a July or August return, and Ben Brown has had multiple stress reactions at the C5 vertebra. Matthew Boyd, Shōta Imanaga, David Peterson, Colin Rea, and Kevin Gausman are all free agents, and Clay Holmes carries a $12 million player option he will most certainly not exercise.

Who’s left? Edward Cabrera, Javier Assad, Jordan Wicks, and maybe Jaxon Wiggins. Perhaps Hoyer can talk Kyle Hendricks out of retirement. I don’t want to say that the rotation situation is dire, but the Cubs seem closer to a rebuilding team than a contending one. I know, I know… Hoyer doesn’t use the “R” word, but when you look at the number of additions it will take to build a competitive pitching staff — including a closer — it may as well be a rebuild. Harper doesn’t get the Cubs any closer to catching the Brewers than keeping Happ, Suzuki, or both will.

I’ll take a hard left into the CBA negotiations to close out. I would personally pass on a cap or a floor, but I wouldn’t mind seeing both sides agree on a free-agent frenzy period similar to the NFL and NBA. Perhaps Hoyer’s biggest enemy is his deliberate pace during the offseason months. Giving front offices a three-week window to sign the game’s top players might prevent Ol’ Jed from overthinking everything.

You know what? Let’s just enjoy the World Series. Baseball will have a little over a month once a champion is crowned before it goes dark.

Cubs News & Notes

• Assistant GM Jared Banner is leaving the Cubs to be the Orioles’ new GM.
• Chicago subsequently tabbed Steve Miller of the Rays to serve as VP of international scouting. Keep on a rockin’ me, baby.
• The Cubs are reportedly planning to retain pitching coach Tommy Hottovy and his assistant Casey Jacobson.
• A quick aside, if I may, regarding this section. MLB prefers to promote the World Series participants this time of year, and rightfully so. That means we are dealing with a lot more speculation than verifiable rumor, at least until the start of November. Always consider the linked source and tread lightly. You can always trust Cubs Insider, of course.
• Ronald Acuña Jr. reportedly wants the Braves to trade him ($). Perhaps your future Chicago outfield looks like Acuña Jr., Harper, and Pete Crow-Armstrong. Don’t hold your breath, and that wouldn’t solve the pitching conundrum.
• Crow-Armstrong opened up about his MVP-caliber season.
• All signs point to an aggressive pursuit of Michael King by Hoyer.
• If you’re looking specifically for trade options, Mason Miller, Logan Gilbert, Shane McClanahan, and Hunter Goodman are potential targets. In order, I’d say yes (depending on cost), yes, maybe, keep Carson Kelly.
• Based on recent history, Guardians outfielder Steven Kwan could enter the offseason on the trade block. Kwan was sixth in baseball in fWAR from June 30 to the end of the regular season. In five seasons in Cleveland, he’s established himself as one of their most important players and among the most underrated in the American League, winning four consecutive Gold Gloves and appearing in two All-Star Games while hitting .282/.382/.349 with a .731 OPS. That checks a lot of Hoyer’s boxes.
• The Cubs could have interest in Kwan, who will likely also draw interest from the Padres and others.
• The North Siders are listed as one team to potentially ascend as the league’s powerhouse franchise if the Dodgers don’t recover. It would be nice, and the team just needs a real pitching staff to be dominant.
• Drumroll please! The best World Series matchup of this century according to ESPN is the 2016 showdown between the Cubs and the (then) Indians.

Ball Four

Things that make you go hmmm…

I would have done this trade, especially since Hoyer ended up trading Rojas, who is going to be a star, for Holmes and Tyrone Taylor. Sure, it’s a big ask, but that’s the price an organization pays when it can’t develop its own pitchers.

Phil's sources say Angels and Mets rejected prospect medicals leading to Cubs acquiring Holmes and Zeferjahn, but not Detmers pic.twitter.com/ZiFDsDji09

— The Cub Reporter (@thecubreporter) October 20, 2026

World Series News & Notes

The Rays beat the Guardians 7-3 on Monday night to win the American League pennant.

If Milwaukee wins the World Series, MLB will be the first of the four major professional sports where the team with the better record won every series.

There are only three players combined on these two teams who have previously appeared in a World Series game: Yandy Díaz (five in 2020), Dustin May (two in 2020 with the Dodgers) and Steven Matz (one in 2015 with the Mets).

A Brewers-Rays matchup inspires both dreams and nightmares, depending on which side of the CBA talks you sit.

Peralta now stands shoulder-to-shoulder with baseball greats Bob Gibson and Walter Johnson.

Both teams carry sportsbook liability heading into their series. Milwaukee opened up the regular season with 35-1 odds to win it all, while Tampa Bay was an 80-1 underdog.

The timing of two small-market teams with low payrolls playing for the Commissioner’s Trophy is hilarious.

Tuesday Stove

The White Sox are predicted to land Japanese slugger Teruaki Sato, who is posting early.

The Phillies are another team that is expected to pursue Kwan if he becomes available.

Bo Bichette has an opt-out clause in his contract but his decision won’t be an easy one.

Aaron Boone is entering the final year of his contract and will be retained to manage the Yankees.

Boone’s lame duck return has a lockout excuse that doesn’t hold water.

Three from the Bill Chuck Files

1. The team that scored first this postseason has won 22 of 34 games.
2. Teams are 22-4 when they outhomer their opponents.
3. The Dodgers and Phillies are the only two teams to reach the postseason each of the last five seasons.

Billy-Ball Bonus

1. This is the fourth World Series featuring two expansion teams.
2. The winner of this series will be a first-time champion.
3. Both teams had the best regular-season home records, the best batting average, and the most wins in their leagues. They also had the best record against winning teams, and each stole over 160 bases this season.

Old school baseball? Possibly, but these are two of the most analytically advanced teams in baseball.

Apropos of Nothing

This year’s Brewers are built a lot more like the 1982 Cardinals than the Harvey’s Wallbangers team that lost to St. Louis in that year’s World Series.

Son of Apropos

I haven’t seen this much excitement in Milwaukee since Lawrence Frank started turning restaurants into supper clubs.

Loose Lips Sink Ships

Orioles owner David Rubenstein said the quiet part out loud, and gleefully at that.

“A lot of my friends were buying teams, and I realized they’re making money. They’re making more money than I’m making in private equity. I thought I should look at it as a financial thing, but ultimately I bought the Orioles for a philanthropic purpose.”

How philanthropic? Rubenstein and the Orioles just had significant layoffs, including the mascot personnel. Why would he do that? Probably because of a looming lockout, but profit is the driver here, so do the math.

Extra Innings

Jake Woodford can get fitted for his ring this week, right?

Regardless of the outcome, one player has already won a World Series ring.

Jake Woodford pitched 23.1 innings for the Brewers this year, got DFA's and later signed with the Rays, pitching 1.1 innings late in the year pic.twitter.com/osNur1mDYd

— Baseball Quotes (@BaseballQuotes1) October 20, 2026

They Said It

• “It’s easy to embrace who and what embraces you. I think for anybody coming in here — opposing players included — it’s very easy to get excited and get up to play here. That’s my experience. I just look forward to playing here every day. The city loves all their sports. And I just want to add to that. And I want to be a part of something that brings people joy.” – Crow-Armstrong

Tuesday Walk-Up Song

Who knew Milwaukee had its own theme song? I did, actually. It’s not bad, either.