Tag: Jeff Montgomery

TWIWBL 95.1 – The Winter Meetings

On June 10, 2026

December 10th

Welcome to the true beginning of Year III of the WBL! We start with the Winter Meetings, and will continue through the Rookie Draft and the Rule V Draft, on our way to Spring Training.

I want to take a moment here to pull the curtain back a little. I’m sure everyone that does these kind of extended, solo play projects has, from time to time, wished they had a partner, a co-commissioner of sorts that could help make judgement calls, look for patterns, initiate trades, etc.

So I’ve tried to build one in Claude. I know some of you may peace out of this thread at this point, but I also wanted to disclose its use. Note that all of the writing and all of the decision making in the WBL remains mine.

This has been, perhaps, the most frustrating thing I’ve ever done with AI. There are two primary obstacles: first, limiting Claude’s view to the OOTP universe and second, overriding Claude’s deeply rooted programming to always agree and to instantly change it’s mind at the faintest whiff of pushback.

CoPilot totally failed on the former, but Claude–with a lot of work on guideline files and the like–does well there. But the second thing … oh my effing god … we’re still trying to find ways to address this.

Anyhow, it’s been an interesting project, and I assume that, as both I get better at the structural architecture beneath the hood and Anthropic continues to improve the product, it will eventually be a stable, pleasant thing.

Onto some team by team notes from the Winter Meetings.

#Baltimore Black Sox

Looking to shore up their bullpen, the Black Sox splashed on a 3 year contract for Jeff Montgomery.

#Chicago American Giants

Chicago signed Hank Aguirre on a 2-year deal for a little less than $600,000–a reasonable flier to take on a starter who was good in 2000, then injured.

#Homestead Grays

The Grays signed Brook Jacoby for some veteran insurance at 3B.

#New York Gothams

In their eternal search for starting pitchers, the Gothams agreed to a 1 year deal with Vic Raschi worth just under $1M.

#Wandering House of David

The House of David signed Dellin Betances, hoping to bolster their bullpen. The 28 year old inked a 3 year, $2.1M contract–pretty reasonable.

TWIWBL 81.6: Effa Manley Division

By mknn

On November 3, 2025

In TWIWBL

Team	W/L	Pct	GB
Brooklyn Royal Giants	88-55	.615	—
Philadelphia Stars	72-70	.507	15.5
Homestead Grays	69-74	.483	19
New York Gothams	68-76	.472	20.5
Ottawa Mounties	66-77	.462	22

Effa Manley Division | 9 September

#Brooklyn Royal Giants

Dickie Thon began a rehab assignment, marking a return from a long term injury.

Two relievers, Jeff Montgomery and Dick Tidrow, announced their retirement. Tidrow amassed 70 somewhat mediocre appearances over his career with the House of David, the New York Black Yankees, and Indianapolis.

Ron Cey hit 2 out, but the Royal Giants were downed by a late inning bullpen collapse, falling to Homestead, 13-4.

#Homestead Grays

Gary Lucas and Nip Winters were recalled from AA champions Syracuse.

#New York Gothams

37 year old minor league 1B Dan Johnson unsurprisingly announced his retirement.

#Ottawa Mounties

Dave Gregg and Mike Dorgan began rehab assignments as they try to make it back to Ottawa before the end of the year.

P Kirk McCaskill retired.

Emerging superstar Roberto Alomar tied a league record with 5 steals in a 9-6 win over the New York Gothams. Alomar had 2 hits and 3 RBIs, giving him 99 on the year, in a game that saw Rusty Staub, Sam Thompson, Gary Carter, and Josh Donaldson all go deep for Ottawa.

#Philadelphia Stars

Minor league pitcher Shane Greene announced his retirement.

Aaron Judge went deep twice and the Stars topped Homestead, 8-3. Charles Rogan improved to 12-9 with 7 shutout innings.

TWIWBL 5.6: Series IV Notes – Marvin Miller Division

By mknn

On May 16, 2021

In TWIWBL

Brooklyn leads the division, with San Francisco and Portland close on their heels. Even this early, a bit of a gap appears between those three teams and Miami and Birmingham at the bottom of the division.

Leading Starters: Don Drysedale, BRK, 3-0, 1.27 ERA, 1.03 WHIP; Walter Johnson, POR, 3-0, 2.54 ERA, 1.16 WHIP; Lefty Grove, SFS, 2-0, 1.57 ERA, 0.78 WHIP.
Leading Relievers: Johan Santana, POR, 7 SV, 1.69 ERA, 1.31 WHIP; Dave Von Ohlen, BRK, 2-0, 2 H, 2.19 ERA.
Leading Batters: Reggie Jackson, SFS, 396/500/679; Bobby Bonds, SFS, 364/432/697; Will Clark, MCG, 211/234/493, 6 HR, 19 RBI; Beals Becker, BRK, 293/408/379, 9 SB; Rickey Henderson, SFS, 250/424/359, 9 SB.

#Birmingham Black Barons

OF Al Schweitzer–one of the better performers for the Black Barons in the early season with a 267/389/422 line–is injured; depending on the duration, a roster move might be looming, with both Dale Murphy (038/194/038) and Chipper Jones (088/238/206) possibly being sent to AAA as part of the transaction.

#Brooklyn Royal Giants

It was an unkind week for the Royal Giants, with both SP Orel Hershiser and 3B Jim Delahanty hitting the injured list. Hershiser will miss close to 2 months with an oblique strain, moving Dick Redding into the rotation. Lefty Frank Knauss was recalled from AAA to take Redding’s slot in the bullpen. Delahanty will be out close to a year, and Duke Farrell was recalled to take his spot, also clearing room for phenom SS/3B Ray Dandridge to move to AAA.

RP Jeff Montgomery–released by Houston–was signed to a minor league contract.

#Miami Cuban Giants

An 0-4 day at the plate against the New York Giants ended Will Clark‘s 10 game RBI streak.

#San Francisco Sea Lions

Dennis Eckersley was put on the 10-Day IL and Carlos Carrasco was demoted to AAA to help address some pitching issues. If, as expected, Eddie Plank is available in a day, the Sea Lions should be fine with the addition of Ps Rick Langford and Diego Segui from AAA.

FA OF Mookie Wilson was signed to a minor league contract.