Hand Reviews — Bobby Winger Ontario’s Rising Poker Star
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- Fact Checked by: PokerListings
- Last updated on: February 10, 2025
We want to take some time to introduce you to a couple of poker players from Ontario that you may or may not know about yet as these two individuals are up and coming players and starting to make waves in the poker world – so when they hit big, you’ll know who introduced them to you first! The two players and Bobby Winger and Jonathan
Bobby Winger is best classified as a semi-pro poker player from the greater Toronto area who began like many amateur poker players did – in the micro stakes online. He stuck to cash and spin n go’s for the most part, playing at the lowest stakes on multiple poker sites. He started making some money and was able to move up to playing $10 and $25 NL cash, and $3 and $5 spins. In September of 2017, Bobby started recording his sessions for posting online and began a YouTube channel – unlike a lot of poker players wanting to share their content, who migrated to Twitch to stream live. Bobby stuck to playing off stream and recording successful sessions in this way.
He tried creating a community by doing challenges for himself – he started with $3 Spin tournaments to make $100, and once that was conquered, he went up to $5 Spins to make another $200, and before he knew it, his bankroll was over $2k. He continued to play $10 and $20 spin tournaments before starting yet another challenge – turning $5 into $500 which took him just over a month to accomplish.
As you can understand, what drives Bobby is a goal and he dedicates himself to achieving that goal by pure grinding. That $500 became the start of a new challenge – grind it up to $5k and he did this by playing spins and tournaments which is when he started winning tournaments online. And unlike a lot of streamers, Bobby is never shy about what his bankroll is on the sites that he plays on, and it seems like he is always on at least one bankroll challenge.
He also climbed to the top of the ranking on GG Poker’s Ontario site for Spins – they employ an ELO rating for players and Bobby was determined to get to the top of that – which he did on March 14th, 2023.
While Bobby was on a bankroll challenge to get to $200k – keep in mind he started playing in the micros back before 2017 – he satellited into the $25k WSOP Super Main Event in The Bahamas this past December for only $150 and turned it into a 114th place finish to win $86,100. While he has had success online, Bobby only had 1 recorded live cash before his win in The Bahamas and it came at the WSOP’s first circuit stop in Toronto in March of 2024 where he placed 62nd in event #2 to win $1,600 CAD.
You should be looking for Bobby’s name in 2025 as he is driven to be the best poker player out there and is not afraid of any challenge in his path – and given where his bankroll is, don’t be surprised if you see him satellite into the WSOP Main Event this year and make a deep run!
Let’s break down a few hands from Bobby:
Hand #1 – Limped to the Big Blind
Here, we find Bobby playing in a $25 Spin n Go with a 2X multiplier. Bobby is in the big blind with Ace-Jack off-suit, and it’s limped to him – he pops it up to 4.5BB, and the button shoves 14.3BB into the middle, covering Bobby. Bobby rolls with it, and you can see the outcome below:
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The question in this hand was whether to jam from the big blind when it’s limped to you in a spin n go with only 14BB back. Bobby is all about maximizing value and making sure when he is ahead of the range of his opponents to not scare them off, so he elects to go for the strong raise here over the shove. As it were, it wouldn’t have mattered if Bobby shoved or not – there was no way pocket kings were folding here, and Bobby gets it in with the worst of it. However, the poker gods were smiling on him, gifting him the ace needed to save his tournament life!
Hand #2 – Heads-Up Clinic
In the second hand we’ll look at, Bobby is playing 100NL against one player and he is in the big blind with around a 100BB stack. Dealt Ace-Two of diamonds, the button raises to $2.40, and he pops it up to $9.50, getting called. On a Six-Four-Three two club flop, he bets $4.51 into a $18.05 pot, which is called. The turn peels off the eight of spades, and he sizes up to $20.12 which is again called by the button. With $66.33 back, and a pot of $67.06, the queen of diamonds leaves Bobby no choice but to shove and fire thrice – and is rewarded the pot with a fold.
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Bobby admitted that it was a bit dicey for him on the river, but the runout wasn’t the worst. However, when you look at how he played the hand, his story was believable enough to his opponent that Bobby had no problem with the low board for the most part. The only critique one could make is on the turn, was that his sizing was going to make it very hard for his opponent to face nothing but a shove on the river, and if that player is willing to essentially chase high cards or a flush draw – hard to think they had any pair as I’d expect a call on the river – then in the future, you might be able to size up more on the turn to extract more value out of them, and when the river bricks, they are going to fold regardless. Still a very interesting hand to go through from both sides and shows Bobby’s fearless attitude at the table!
Hand #3 – Quicksand
In this hand, Bobby is heads-up in a $25 spin, 2X multiplier and Bobby is sitting with 24BB, while his opponent has 51BB to start the hand. On the button with Six-Five of clubs, he limps pre and gets to see a cheap flop of Queen-Nine-Three, two spades. He min bets the flop which gets called. The turn brings the seven of spades which brings an overbet of 5BB from Bobby – which is also called. The river is the Queen of diamonds and Bobby lets it rips all in – 17BB into a 14BB pot. The aftermath is below.
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In hindsight, his shove on the river should have worked – Bobby sensed weakness through the entire hand leading up to the river, which is why he shoved, but somehow, they found a call with two pair on a three to a flush, paired board. Even if Bobby’s opponent feels that Bobby is weak – limping pre, min betting the flop, and then overbetting the turn, if you are going to hero call with top and third pair in that situation, you need to have a strong read on your opponent to realize when they are simply triple barreling on you and bluffing with nothing. According to Bobby, they have met and played before, so there is info between them, but if you are going to try and pull off a stone-cold bluff – like in the second hand we went through, make your story believable beginning to end. Bobby’s range would have been huge limping pre-flop as he did, and the min bet may have looked like he wanted them to call, but to me this hand went awry on the turn with the overbet. Heads-up – why would you want to push your opponent off of a hand when you make your flush? Didn’t make sense, and then the Queen on the river reduces the changes Bobby had a queen, so the only hand I suspect Bobby’s opponent was afraid of was 9x, to which he was prepared to call off with his seven.
Hand #4 – As The World Turns
We find Bobby in his sweet spot – a $25 Spin with a 3X multiplier. He’s heads-up but with only 8.13BB vs his opponent with 29.4BB and Bobby’s in the big blind with Queen-Two of diamonds. The button limps and Bobby takes the free flop of Ace-Eight-Four rainbow. The turn comes another diamond – the three, and the button bets 2BB – pot. Bobby goes for it, and shoves 7.13BB into the middle, inducing a fold.
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Bobby’s opponent only had to call 5.13BB into a 6 BB pot to take a shot at winning this spin but elects to fold to fight another hand. The approach is interesting – limping heads-up can be a curious move – it can be a sign of strength or pure weakness hoping to hit a flop. But when the board comes as it does, and the button checks, Bobby can be convinced that he’s either up against a monster or nothing. The turn giving him outs provides enough for Bobby to put his weak opponent to the test. It’s spots like this that really show Bobby’s skills when it comes to reading hands and opponents in these spots – which he was correct in this case. He won the battle here but lost the war eventually.
Hand #5 – Deal or No Deal!
In our final hand review, Bobby is heads-up in a $500 buy-in ON-COOP tournament – the equivalent to WCOOP for the global Stars players – and he turned down a deal with his opponent. With the chip stacks at 40BB for Bobby and 53BB for his opponent, Bobby picks up Jack-Six of spades in the big blind and calls a raise of 2.1BB. The flop comes Queen-Five-Four with two spades and the button bets 2.27BB – half pot – to which Bobby calls. The turn is the three of diamonds and induces a 7.4BB bet into a 9BB pot. Bobby with the straight and flush draws shoves his remaining 32.8BB. Much to Bobby’s surprise – he is called, and this is the result.
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Bobby put him on a hand that would have been difficult to call Bobby’s shove with, given the number of draws Bobby has and the number of combos, giving Bobby a lot of fold equity here. It’s an interesting spot given you are playing for the title as well but ultimately his opponent was not willing to let top pair plus a gut shot straight draw go and gambles for a roughly $3k jump from second to first. Should he have taken the deal – maybe, but hindsight is always 20/20 isn’t it?
Bobby Winger’s success over the last three months should not be seen as a blip on the radar – PokerWinger is going to have a big 2025 given the success he’s had over the last 8 years playing online. Hard to imagine how Bobby doesn’t get a six-figure live score under his belt sooner than later – but because he plays in the fenced in area of Ontario, very few online pros know who he is, which will suit Bobby just fine when the day comes!
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