Jimmie May shines in the Heads-Up Podcast Showdown

The latest episode of the Poker Gods Heads-Up Podcast was a rollercoaster ride, filled with fearless aggression, momentum shifts, and a dramatic finish as Jimmie May battled back to defeat host Kasey Orr.

⸻

Fast Start from Jimmie

From the outset, Jimmie brought the heat. His aggressive style had Kasey on the defensive, as he applied relentless pressure and chipped away with raises and bets. It looked like Jimmie might bulldoze his way to victory—until a series of crucial hands completely flipped the momentum.

⸻

Crucial Hand #1 – The Failed Bluff

The first turning point came with the blinds at 10,000/15,000 with a 15,000 ante.

• Preflop: Kasey picked up K♠9♣ in position and raised to 45,000. Jimmie defended his big blind with 8♣6♦.

• Flop (J♦9♥7♦): Both players checked, leaving the tension to build.

• Turn (9♠): Jimmie tried to seize control, betting 50,000 into roughly 100k. Kasey, now holding trips, just called, adjusting his strategy to trap after picking up on Jimmie’s bluff-heavy tendencies.

• River (4♠): A blank card. Jimmie pulled the trigger with a bluff of 84,000. After tanking, Kasey made the call and scooped the pot with trip nines.

This pot gave Kasey both chips and confidence while confirming that Jimmie was willing to push bluffs deep into hands.

⸻

Crucial Hand #2 – Straight Over Straight

The real drama came a few hands later in a massive cooler.

• Preflop: Kasey limped the button with 6♣7♦, and Jimmie checked his option with 2♦3♣.

• Flop (3♥5♠8♠): Jimmie paired his three and kept the aggression going, betting 20,000. Kasey, with a gutshot draw, made the call.

• Turn (6♦): Both players improved—Jimmie to draw and a Pair and Kasey to middle pair plus his original straight draw. Jimmie bet 25,000, and Kasey called again.

• River (4♣): The dream card. Both players made a straight—Jimmie holding the wheel, Kasey with the higher one. Jimmie checked, and Kasey went for max pressure with an overbet of 150,000.

Jimmie went deep into the tank, muttering: “So you’re repping a 7… hang on, I gotta figure you out.” Believing Kasey might be bluffing, he made the call—only to see the bad news.

Kasey dragged a monster 435,000-chip pot, boosting his stack to 779,000 (52 BB), while Jimmie was left with just 221,000 (15 BB).

⸻

Crucial Hand #3 – The Bluff That Doomed Kasey

Just as Kasey looked poised to close things out, the tides turned again with the blinds up to 10,000/25,000 with a 25,000 ante.

• Preflop: Kasey opened the button with A♠2♦, raising to 60,000. Jimmie looked down at A♦7♥ in the big blind and 3-bet to 160,000. Kasey called in position.

• Flop (K♥6♥J♠): Jimmie checked, and Kasey bet 65,000 with ace-high. After a long tank, Jimmie called, not convinced.

• Turn (7♣): The perfect card for Jimmie—pairing his seven. He checked again, and Kasey decided to keep his bluff going, firing 65,000 to make it look like thin value.

• The Jam: Jimmie shoved all in, putting maximum pressure on Kasey’s stack. With only ace-high and no outs, Kasey had to fold.

Jimmie revealed the strength afterward, showing he had in fact paired the turn. He scooped a 752,000-chip pot, flipping the script and leaving Kasey crippled in an all-in or fold scenario for the remainder of the show.

⸻

Jimmie’s Comeback & Final Hand

From there, Jimmie never looked back. He continued applying pressure, forcing Kasey into tough spots. In the final clash, Jimmie once again went for maximum pressure on the river. Kasey, remembering earlier bluffs, convinced himself Jimmie might be at it again and made the big call. But this time, Jimmie had the goods. He tabled the winner and locked up victory in one of the most dramatic Heads-Up Podcast battles to date.

⸻

Conclusion

This showdown had everything: a failed bluff, a brutal straight-over-straight cooler, and the defining moment when Jimmie’s A♦7♥ shove took control of the match. Kasey adjusted well, trapping after spotting Jimmie’s bluffing frequency, and nearly closed it out. But in the end, it was Jimmie’s resilience, relentless aggression, and one perfectly timed shove that sealed his comeback victory.