Memoirs + manifestos + musings of a horse racing managing partner + soccer club co-owner in Maine
Thursday, April 30, 2026
Headlines: U.S. Open Cup Round of 16 Review
For the second year in a row and just the fourth time in the Modern Era (1995-present), the Quarterfinals of the Lamar Hunt US Open Cup will be full of Major League Soccer teams. The 2026 US Open Cup champion will be guaranteed to be a team from MLS after the three remaining lower division teams all went on the road and crashed out in the Round of 16. One Knoxville SC fell to the Columbus Crew 4-1 followed by Louisville City taking the Houston Dynamo to extra time before falling 2-1. The round concluded on Wednesday night with the Colorado Springs Switchbacks taking the Colorado Rapids to penalty kicks, but the MLS original prevailed.
Lists: Favorite Kentucky Derby Horses (Since 2019)
(A series of lists of favorite things.)
- Maximum Security (2019)
- Mo Donegal (2022)
- Journalism (2025)
- Coal Battle (2025)
- Authentic (2020)
- Tiz The Law (2020)
- West Saratoga (2024)
- Forever Young (2024)
- Mandaloun (2021)
- Hot Rod Charile (2021)
IPS 365: Wednesday, April 29 (Day No. 130)
(This is a day-to-day look at being the founder and managing partner of the Ivory Pine Syndicate, a Maine-based horse racing partnership.)
- Didn't do any work related to Ivory Pine Syndicate
RSC 365: Wednesday, April 29 (Day No. 332)
(A day-to-day look at being the chairman and a co-owner of the Rosevelt Soccer Club, a soccer club based in Gorham, Maine.)
- Created and scheduled a 23U player announcement post
- Texted 23U coach about a news release
- Texted a coach about schedule logistics
- Texted a photographer about schedule logistics
- Texted with a club president about schedule logistics
- E-mailed facilities manager about field logistics
- Posted 23U news release on club website
- Researched high school athletics schedules
- E-mailed state association about schedule logistics
- Texted with coaches about schedule logistics
- Worked on schedule logistics
- Texted with coaches about schedule logistics
- Scheduled 23U news release post
- Talked with a club president about schedule logistics
- E-mailed coaches and a club president about schedule logistics
Road to the NHC: Wednesday, April 29 (Day No. 40)
(This series will feature practice mythical $2 Win and $2 Place wagers each day at Throughbred race tracks.)
Bankroll: $108.82
Win Wagers: N/A
Place Wagers: N/A
Win %: 17% (6/36)
Place %: 44% (16/36)
Wednesday, April 29, 2026
Bookshelf: Thirty Tons a Day (Chapter 17)
Thirty Tons a Day: The Rough-Riding Education of a Neophyte Racetrack Operator (Bill Veeck and Ed Linn)
Chapter 17: The Voracious Animal, Eating Itself Up
Veeck details the financial difficulties of Suffolk Downs's parent company Realty Equities, and connects those financial issues to his short-lived ownership of the racetrack.
IPS 365: Tuesday, April 28 (Day No. 130)
(This is a day-to-day look at being the founder and managing partner of the Ivory Pine Syndicate, a Maine-based horse racing partnership.)
- Confirmed Crimson Pine's entry
RSC 365: Tuesday, April 28 (Day No. 331)
(A day-to-day look at being the chairman and a co-owner of the Rosevelt Soccer Club, a soccer club based in Gorham, Maine.)
- Handicapped soccer games
- Texted with coaches about schedule logistics
- Talked with a director about referee logistics
- Texted with a director and coaches about roster logistics
- Texted with a coach about schedule logistics
- Texted with a coach about schedule logistics
- Texted with a photographer about schedule logistics
- Worked on 2026-2027 Player Evaluation graphics
- Researched 2026-2027 Player Evaluation dates
- E-mailed facilities manager about field logistics
- Updated results tracker
- Updated Positive Developmental Experiences (PDE) graphic
- Texted with coaches about schedule logistics
- E-mailed 23U league director to confirm registration
- Created 23U league announcement graphic
- E-mailed 23U players
- Measured fields and goals
- Coached 12U session
- Talked with a club president about schedule logistics
Road to the NHC: Tuesday, April 28 (Day No. 39)
(This series will feature practice mythical $2 Win and $2 Place wagers each day at Throughbred race tracks.)
Bankroll: $108.82
Win Wagers: N/A
Place Wagers: N/A
Win %: 17% (6/36)
Place %: 44% (16/36)
Tuesday, April 28, 2026
Headlines: U.S. Open Cup Round of 16 Preview
With two matches on Tuesday and the remaining six on Wednesday, eight teams will move to within three wins of a Lamar Hunt US Open Cup championship and a spot in the 2027 CONCACAF Champions Cup. Three lower division clubs are among the Final 16, Louisville City and Colorado Springs Switchbacks from the Division 2 USL Championship and One Knoxville from third-tier USL League One. One Knoxville also won the $50,000 prize for the Division 3 club going furthest in this year’s tournament.
Quote, Unquote: Hunter S. Thompson
IPS 365: Monday, April 27 (Day No. 129)
(This is a day-to-day look at being the founder and managing partner of the Ivory Pine Syndicate, a Maine-based horse racing partnership.)
- Researched Kentucky Derby horses
- Listened to Ron Flatter Racing Pod
RSC 365: Monday, April 27 (Day No. 330)
(A day-to-day look at being the chairman and a co-owner of the Rosevelt Soccer Club, a soccer club based in Gorham, Maine.)
- Handicapped soccer games
- Updated 23U player announcement graphics
- Created and scheduled 23U player announcement graphic
- E-mailed coach about schedule logistics
- Talked with a director about referee logistics
- Texted with a Classic Club president about field logistics
- Updated master game schedule
- Texted with club directors about potential friendlies
- Texted a director about referee logistics
- Worked on 23U player announcement graphics
- Talked with a director about schedule logistics
- Read The National Team
- Worked on updated FAQ about Presidents Cup
- Checked in with 10U, 12U, 13U, 14U, and 15U coaches
- Talked with a member about a variety of topics
- Texted a club president about upcoming game schedules
- Surveyed practice fields
- Talked with a director about a variety of topics
- E-mailed updated Presidents Cup FAQ to members
- E-mailed schedule updates to 16U and Academy teams
- E-mailed update to members about disciplinary matter
Road to the NHC: Monday, April 27 (Day No. 38)
(This series will feature practice mythical $2 Win and $2 Place wagers each day at Throughbred race tracks.)
Bankroll: $108.82
Win Wagers: N/A
Place Wagers: N/A
Win %: 17% (6/36)
Place %: 44% (16/36)
Monday, April 27, 2026
Bookshelf: The National Team (Chapter 16)
The National Team: The Inside Story of the Women Who Changed Soccer (Caitlin Murray)
Chapter 16: "Let's Give This League a Shot, Let's Go For It"
Murray opens the third section of her book with the details of a post-game meeting between the USWNT and the U.S. Soccer Federation in Hartford on October 12, 2012.
The topic was yet another women's professional league, and the remainder of this chapter analyzes the development of the National Women's Soccer League (NWSL), which is now the longest-running women's professional soccer league in U.S. history.
A key difference between this league and previous attempts was the buy-in among the federations in Canada, Mexico, and the United States to subsidize the salaries of national team mainstays to relieve the financial burden of individual clubs.
IPS 365: Sunday, April 26 (Day No. 128)
(This is a day-to-day look at being the founder and managing partner of the Ivory Pine Syndicate, a Maine-based horse racing partnership.)
- Researched Plainridge Park conditions sheets
- Researched Crimson Pine's U.S. Trotting Association (USTA) profile
RSC 365: Sunday, April 26 (Day No. 329)
(A day-to-day look at being the chairman and a co-owner of the Rosevelt Soccer Club, a soccer club based in Gorham, Maine.)
- Created social media graphics for game day schedules
- E-mailed 23U player about player announcement graphics
- E-mailed coaches about Presidents Cup schedule and roster logistics
- Updated 9U and 10U game schedules
- Prepared for coaching 12U game
- Prepared for coaching RSC Academy game
- Coached and recorded 12U game
- Recorded 12U game
- Worked with a director to review field conditions at training fields
- Watched 12U game
- Talked with a club president about a variety of topics
- Updated 9U and 10U game schedules
- Updated training session schedules
- Drafted club update
- E-mailed club update to members
- Texted coaches about modified training session schedules
- Coached RSC Academy game
- Texted with coaches about schedule logistics
Road to the NHC: Sunday, April 26 (Day No. 37)
(This series will feature practice mythical $2 Win and $2 Place wagers each day at Throughbred race tracks.)
Bankroll: $108.82
Win Wagers: N/A
Place Wagers: N/A
Win %: 17% (6/36)
Place %: 44% (16/36)
Sunday, April 26, 2026
Soccer Weekend: Sunday, April 26 (Wager No. 73)
(This feature will focus on a $1 parlay wager every Saturday and Sunday through the end of May.)
Game No. 1 (10:30a)
Men's Allsvenskan (Sweden)
IFK Göteborg (+160)
Game No. 2 (11:30a)
Men's Bundesliga (Germany)
Borussia Dortmund (-275)
Pick Success Rate: 59% (86/146)
Total Bankroll: $42.31 (+ 5.8%)
IPS 365: Saturday, April 25 (Day No. 127)
(This is a day-to-day look at being the founder and managing partner of the Ivory Pine Syndicate, a Maine-based horse racing partnership.)
- Wrote training checks
- Bought pastries at The Baker's Bench for caretakers
- Bought carrots for pacers
- Visited Crimson Pine and Tayra
- Talked with trainer
- Handicapped and attended races at First Tracks Cumberland
- Handicapped and watched races at Aqueduct, Churchill Downs, Evangeline Downs, Gulfstream Park, and Santa Anita Park
RSC 365: Saturday, April 25 (Day No. 328)
(A day-to-day look at being the chairman and a co-owner of the Rosevelt Soccer Club, a soccer club based in Gorham, Maine.)
- Texted with a club director about field logistics
- Confirmed game schedules
- Called a coach to confirm schedule logistics
- Uploaded Veo game footage
Road to the NHC: Saturday, April 25 (Day No. 36)
(This series will feature practice mythical $2 Win and $2 Place wagers each day at Throughbred race tracks.)
Bankroll: $108.82
Win Wagers: $3.40
Place Wagers: $2.20
Win %: 17% (6/36)
Place %: 44% (16/36)
Saturday, April 25, 2026
Soccer Weekend: Saturday, April 25 (Wager No. 72)
(This feature will focus on a $1 parlay wager every Saturday and Sunday through the end of May.)
Game No. 1 (10a)
Men's Championship (England)
Birmingham City FC (-130)
Game No. 2 (11a)
Men's Superettan (Sweden)
Örebro SK (+100)
Pick Success Rate: 59% (85/144)
Total Bankroll: $43.31 (+ 8.3%)
RSC 365: Friday, April 24 (Day No. 327)
(A day-to-day look at being the chairman and a co-owner of the Rosevelt Soccer Club, a soccer club based in Gorham, Maine.)
- Talked with a director about Presidents Cup logistics
- Worked with a director to organize referee fees and team rosters
- Mailed payment to field vendor
- Called a club director about schedule logistics
- Texted with a director and coaches about schedule logistics
- Texted with a coach about Presidents Cup logistics
- Texted with a director about field logistics
- Listened to The Friggin' Soccer Show podcast
- Texted with a director and coaches about schedule logistics
- E-mailed a club director about schedule logistics
- Talked with a director about schedule logistics
- Checked a team's schedule
- Texted with a director and coaches about schedule logistics
- Texted with club coaches about 23U programming
Road to the NHC: Friday, April 24 (Day No. 35)
(This series will feature practice mythical $2 Win and $2 Place wagers each day at Throughbred race tracks.)
Bankroll: $103.22
Win Wagers: $3.40
Place Wagers: $2.20
Win %: 17% (6/36)
Place %: 44% (16/36)
IPS 365: Friday, April 24 (Day No. 126)
(This is a day-to-day look at being the founder and managing partner of the Ivory Pine Syndicate, a Maine-based horse racing partnership.)
- Handicapped and watched races at Evangeline Downs, First Tracks Cumberland, and Keeneland Race Course
Friday, April 24, 2026
IPS 365: Thursday, April 23 (Day No. 125)
(This is a day-to-day look at being the founder and managing partner of the Ivory Pine Syndicate, a Maine-based horse racing partnership.)
- Handicapped and watched races at Keeneland Race Course
RSC 365: Thursday, April 23 (Day No. 326)
(A day-to-day look at being the chairman and a co-owner of the Rosevelt Soccer Club, a soccer club based in Gorham, Maine.)
- Created and posted 23U player announcement graphic on club socials
- Forwarded Presidents Cup update to coaches
- Texted with Classic Club director about field logistics
- Texted with director about registration logistics
- E-mailed league director about registration logistics
- Talked with a member about injury logistics
- Called coaches about discipline issues
Road to the NHC: Thursday, April 23 (Day No. 34)
(This series will feature practice mythical $2 Win and $2 Place wagers each day at Throughbred race tracks.)
Bankroll: $95.80
Win Wagers: N/A
Place Wagers: N/A
Win %: 12% (4/34)
Place %: 41% (14/34)
Thursday, April 23, 2026
Lists: Most Memorable IPS Wins
(A series of lists of favorite things.)
- Sixby Hanover (May 21, 2022: First Tracks Cumberland)
- Sixby Hanover (August 18, 2023: Skowhegan State Fairgrounds)
- Crimson Pine (June 23, 2023: First Tracks Cumberland)
- Sixby Hanover (April 21, 2023: First Tracks Cumberland)
- Crimson Pine (October 3, 2025: Plainridge Park)
- Sixby Hanover (August 9, 2022: Topsham Fairgrounds)
- Crimson Pine (July 17, 2025: Plainridge Park)
- Sixby Hanover (November 24, 2024: First Tracks Cumberland)
- Crimson Pine (September 30, 2024: Plainridge Park)
- Crimson Pine (October 14, 2025: Plainridge Park)

























