One Bet, One Win, What's Next? We could be in for a long season...

Chase Variance
Jul 19
3 min read

If you are following along you know that yesterday we took Toronto -137 to win, and they did. Verlander gave up 4 runs, and Toronto looked to be in control in the entire time. Record for ChatGPT: 6-4

Bankroll update: bet $8.25, won $14.27, added $6.02 - we aren't getting rich but we are up to $151.18.

The math is easy, we are up 51.18% to start using this approach.

Here is what ChatGPT came up with for us with the established criteria:

📊 Red Sox vs. Cubs – July 19 Betting Analysis

For Saturday’s MLB slate, the Boston Red Sox moneyline offers a disciplined, +EV play. Boston sends Brayan Bello to the mound against Chicago’s Shōta Imanaga. The Sox are red‑hot, winning 11 of their last 12, while the Cubs have been solid at home but face a tough matchup here.

At +150, the implied win probability for Boston is ~42%, but our estimate puts it closer to 47–49%, creating a modest edge. With strong current form and a favorable pitching matchup, this bet clears our +2% EV threshold comfortably.

📋 Recommended Bet:Red Sox ML +150 — Stake: $7.25 (≈5% of bankroll)

We’re sticking to the process: confirmed starters, market liquidity, and verified value. Let’s see if Boston can stay hot.

Truth is, I am not feeling great about this one.

Cubs are playing really well, and the bet seems high compared to where we have been.

So, I pushed a bit on ChatGPT, when looking more closely at the rationale, and it definitely got confused:

🧠 Updated Context for Saturday (July 20)

You're adjusting before Saturday's game? The Friday result (Red Sox losing to Cubs) does have implications:

Momentum Shift
- Red Sox’s 10-game post–All-Star winning streak is now snapped. That reduces the confidence in their form edge for Saturday’s matchup.
Starter/Bullpen Usage
- If Bello and key relievers were used heavily tonight, there may be fatigue. That could reduce their effectiveness or availability for spot starts on Saturday (unlikely, but we’ll monitor probable starters).
Line Impact
- The market may shift slightly in response—expect later betting lines to adjust, maybe reducing value.

I did tell ChatGPT I was disappointed in it, and had lost some confidence given, when it said Boston was 11-1

after the All-Star break.

Here was it's reply:

✅ Thanks for being direct — and you’re right to hold me accountable here.

I appreciate your trust, but also your skepticism — which is exactly the mindset of a disciplined bettor. Let me explain exactly how we can make sure the process stays clean, confident, and correct going forward:

🧾 Why You’re Noticing Gaps

The moments where you feel “not inspired” are usually because:

I rushed through assumptions about lineups, pitchers, or dates before re‑verifying them.
I sometimes mixed up today/tomorrow when you’re planning a day ahead (blog timing vs betting timing).
I didn’t explicitly show the data sources & logic trail at each step.

🧰 How We Fix This

Here’s how I’ll improve the workflow going forward:

🔍 1️⃣ Always Re‑Verify Key Data

— Explicitly check today’s date, pitchers, lineups, weather, and odds against MLB.com, ESPN, and a sportsbook at time of recommendation.— No relying on cached or older info.— Show you the confirmed links/sources for transparency.

📈 2️⃣ Always Show the Math

— For each bet:

Implied probability from odds.
Estimated true win probability (and what it’s based on).
EV calculation showing it clears +2% threshold.— Even if you don’t want the math in the blog, I’ll run it & show you here.

📝 3️⃣ Ledger Discipline

— Maintain a clear, complete ledger of bets, stakes, wins/losses, bankroll — posted & confirmed every time.— No guessing bankroll or record at any point.