
AI Best Bets: Maybe AI Isn’t a Sure-Fire Win After All
Perplexity’s first ugly week forces a reset as the betting experiment heads into the NBA and Stanley Cup Finals.

Heading into last week, our AI best bets experiment was on a roll, up nearly nine units over the first four weeks. And then… last week happened, and our AI bookmaker ended up way off the mark.
This was the first time Perplexity, or as I’ve come to call it, Perp, experienced a truly rough week of sports betting since our experiment began.
A Thunder money line bet instead saw the San Antonio blow out OKC 118–91. The Hurricanes won, but the game went over 5.5 goals. Djokovic was upset in his Friday match. And the Athletics scored 8 runs in a loss to the Yankees.
That’s a big old goose egg. We lost four units in the week.
But we can take something away from this: The process wasn't broken. Variance just hit hard. The AI was fine on the reads, but the portfolio got hit by one bad side, one bad total, one upset, and one noisy MLB loss.
This week, we’ll reset Perp with a cleaner approach to AI sports betting.
Last week’s AI Bets results
| Bet | Result | Units |
|---|---|---|
| Thunder ML | Lost | -1.0 |
| Hurricanes ML and game U/5.5 | Loss | -1.0 |
| Djokovic win | Loss | -1.0 |
| Yankees ML, Athletics U/4.5 runs | Loss | -1.0 |
| Weekly Total | Loss | -4.0 |
What We're Doing Differently This Week
We're not chasing to make up the losses. Both the human and AI sides were a little overconfident heading into last week after the initial success.
Now, we’re executing cleaner shots with better correlation. That means small, single bets or two-leg parlays only, matching props to final results, and avoiding big multi-leg shots.
We're leaning heavier into Game 1 NBA Finals angles, adding Game 2 NHL Stanley Cup picks, and grabbing solid late-week MLB bets when the market opens up.

NBA - San Antonio vs. New York, NBA Finals Game 1
The 2026 NBA Finals start Wednesday when the New York Knicks head to San Antonio. The Spurs opened as -210 favorites in the series after eliminating the Thunder in the Western Conference Finals.
Game 1 is where the best angles live. For Perp, the cleanest bet is:
- Over 217.5 total points
"Game 1 openers often ride pace and hot starts, and the pricing is in the high-217 range. This is the best AI-style total of the week.”
- Jalen Brunson over points
"Brunson is the Knicks' engine and should carry a massive offensive load in the series. Pairing him with the over gives you a clean two-leg card."
That's the 2-leg NBA card for the week:
- Over 217.5 total points
- Brunson over points
NHL - Vegas vs. Carolina, Stanley Cup Final Game 2
The NHL is swinging into the Stanley Cup Final, and Game 2 is usually when the better team establishes the tone.
For Perp, the cleanest bets:
- Over 5.5 total goals
"Game 2 tends to open up more than Game 1. The over is the cleanest companion to the favorite's puck line.”
- Jack Eichel anytime goalscorer
"Eichel has 7 goals in 16 playoff games, scored the OT winner vs. Colorado in the WCF, and is Vegas' best scorer. He's the cleanest Vegas goalscorer prop."
Split the two up as singles, or combine for a simple NHL card for the week:
- Over 5.5 total goals
- Eichel anytime goal

MLB – Late Week Game
We’ll come back to Perp later in the week when we know pitching matchups and how the beginning of the week shapes up, and ask for two MLB bets.
The AI bookmaker has been fairly solid throughout our experiment, figuring out pitcher props and how they correlate to final results, so we’ll look for that.
Card Table for June 1-7
| DATE | GAME | BET | RISK LEVEL |
|---|---|---|---|
| June 3 | Knicks vs. Spurs, Game 1 | Over 217.5, Jalen Brunson over points | Medium |
| June 4 | Vegas vs. Carolina | Over 5.5 total goals | Low |
| June 4 | Vegas vs. Carolina | Jack Eichel anytime goalscorer | Medium |
| June 5 | MLB single prop | TBD | Medium |
| June 6 | MLB two-leg parlay | TBD | High |
The Key Takeaway
This week is about resetting the process, not chasing to make up for our losses. We need to practice responsible gambling habits and not end up further in the hole.
The first disastrous week happened, but the edge is still there. It just executed messily and hit a bad luck streak. We're avoiding big parlays, staying with at most two legs, and focusing on the NBA Finals, Stanley Cup Final, and a pair of late-week MLB wagers.
Last week was the first time the AI missed on every bet, and the portfolio got hit hard. This week is about discipline.
Let's get right to it.
AI Bets Running Total
| WEEK | NOTES | UNITS |
|---|---|---|
| Week 1 | AI Yankee love begins | 4.0 |
| Week 2 | Mixed NBA slate, but still ahead | 1.5 |
| Week 3 | Caufield's prop helps salvage the week | 1.75 |
| Week 4 | Brunson saves the day | 1.2 |
| Week 5 | Bad beat week | -4.0 |
| Five-week total | Running profit | +4.45 |

Pat Evans is a Grand Rapids-based journalist and editor covering the intersection of business, sports, lifestyle, and gambling regulation. With a background in business journalism and legislative reporting (LSR, iGamingBusiness), he brings an analytical, human-focused approach to stories about modern trends. His work has appeared in regional and national publications, and he is also the author of two books on beer history.
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