Canada
Playmaker Commences Trading on TSXV; Jake Cassaday announced as Chief Operating Officer to bolster growth initiatives

Playmaker Capital Inc., the Toronto-based, newly-listed digital ecosystem for sports fans, is pleased to announced that trading in its common shares on the TSX Venture Exchange (the “TSXV”) will commence today at 9:30 a.m. under the ticker symbol “PMKR”. Playmaker is also pleased to announce the appointment of Jake Cassaday as Chief Operating Officer. Mr. Cassaday was previously a Partner at Relay Ventures, a prominent North American venture capital fund and lead investor behind Playmaker.
Playmaker has a mission to aggregate an ecosystem of engaged sports fans that will be monetized with sports betting companies, blue chip advertisers, leagues and teams. Playmaker’s vision is to apply an intentional and thoughtful approach to becoming a strategic aggregator of sports fans, the true lifeblood of the sports betting industry.
As previously announced, in April 2021, Playmaker completed its first acquisition, Futbol Sites, a leading digital sports media group connecting brands and sports betting operators to millions of fans in Latin America and the U.S. Playmaker anticipates making further acquisitions focused on brands with high-quality assets and solid management teams with a demonstrable track record for sustained growth and profitability.
Playmaker is led by an experienced management team that is well positioned to achieve the goals set out for the organization. In executive officers, Jordan Gnat (Chief Executive Officer), Jake Cassaday (Chief Operating Officer), Mike Cooke (Chief Financial Officer) and Federico Grinberg (Executive Vice President), Playmaker has decades of transaction and industry experience in both the digital media and sports betting sectors. The board of directors is led by Chair Maryann Turcke, currently serving on the board of directors of the Royal Bank of Canada, and previously Chief Operating Officer of the National Football League (NFL) and President of Bell Media.
“Today marks the next step in Playmaker’s journey to become a global player in digital sports media. We will leverage our experienced management team and exceptional board of directors to bring great value to our shareholders,” commented Jordan Gnat, Chief Executive Officer of Playmaker. “These are exciting times in the early life of Playmaker. Our mission is to build an ecosystem of assets that will provide sports fans and our clients with outsized value. We are beginning from an already-profitable position, and now we welcome Jake Cassaday as Chief Operating Officer.”
“To be joining Playmaker, fresh on the heels of a go-public, and ready to scale through both organic and acquisitive growth, is hugely exciting for me,” added Jake Cassaday. “Playmaker connects my passions for sports, technology, and media, and allows me to leverage my experience to support the Playmaker growth engine and build a lasting company in the sports media arena.”
Before joining Playmaker, Mr. Cassaday enjoyed a six-year tenure at Relay Ventures where he served on the board of directors of several high-growth companies, and as an advisor to startup accelerators, including Techstars and the Future of Sport Lab. Mr. Cassaday has been heavily involved with Playmaker since its inception, helping to build out its strategy, raise capital, and carry out initial acquisitions. He holds an MBA from the University of Toronto’s Rotman School of Management and a BA from McGill University.
Canada
OLG Selects Caesars Entertainment as the Service Provider for Windsor Casino

The Ontario Lottery and Gaming Corporation has selected Caesars Entertainment as the Service Provider in the Windsor Casino procurement process. This is the final procurement process in the OLG’s land-based gaming modernization initiative.
Tom Reeg, CEO of Caesars Entertainment, said: “We are thrilled to be selected as the service provider for the Windsor Casino by the OLG. Caesars has a long history of managing Windsor and looks forward to continuing to deliver exceptional guest service and experiences at the property.”
Caesars and its predecessor companies have partnered with the OLG to operate Caesars Windsor (fka. Casino Windsor) since the opening of the temporary facility in 1994. Caesars will assume responsibility for gaming and non-gaming operations of the Windsor casino on behalf of the OLG under a 20-year operating agreement, which is expected to begin in 2026.
OLG requires an 18-month restriction on any organizational changes consistent with other gaming bundle modernizations in Ontario. Unionized employees will continue to be governed by the terms of their collective agreement.
Canada
AGCO issues penalties of $151,000 against Great Canadian Entertainment for alleged age verification failures

The Alcohol and Gaming Commission of Ontario (AGCO) has issued $151,000 in penalties to Great Canadian Entertainment for allegedly failing to prevent minors from accessing gambling on multiple occasions at three Toronto-area casinos.
As part of its investigation, the AGCO reviewed four separate incidents in which minors allegedly gained access to the casino floors and in which some of these minors participated in gambling activities – two cases at Great Canadian Casino Resort Toronto, and one at each of Casino Ajax and Pickering Casino Resort.
The AGCO is committed to ensuring casinos meet Ontario’s high standards of harm reduction and responsible gambling. The AGCO’s Standards require operators to ensure only eligible individuals are permitted into a gambling site and strictly prohibit access to anyone under 19 years of age (except in the course of employment). The Standards also mandate that casino employees have the necessary competence, skills, experience and training to effectively carry out their duties, including age verification.
This enforcement action underscores the AGCO’s dedication to protecting youth and other vulnerable individuals.
A casino operator served with an Order of Monetary Penalty by the AGCO Registrar has the right to appeal the Registrar’s decision to the Licence Appeal Tribunal (LAT), an adjudicative tribunal that is part of Tribunals Ontario and independent of the AGCO.
“Ontario casino operators have an obligation to ensure minors are not able to access casino floors or activities such as slot machines or table games. The AGCO will continue to monitor and hold all casino operators accountable for fulfilling this important role.” – Dr. Karin Schnarr, Chief Executive Officer and Registrar, AGCO.
Canada
ToonieBet Launches its Sportsbook on Apple App Store and Google Play Store

ToonieBet, Soft2Bet’s flagship online casino and sportsbook for Ontario, has officially launched its sportsbook on the Apple App Store and Google Play Store. The platform is tailored specifically for local players, offering a dynamic betting experience with a broad range of sports events and competitive odds. The platform also features personalised promotions and loyalty rewards designed to match the preferences of Ontario’s diverse betting community.
The sportsbook uses official data feeds, ensuring players have access to the most accurate and up-to-date information on top local and international sports events. Additionally, the platform offers live broadcasting with real-time match analytics, allowing users to make informed betting decisions as events unfold. Integrated with MEGA and advanced player account management features, the operator is committed to delivering a seamless and responsible gaming environment that enhances the overall player experience while supporting local sports initiatives.
As part of this launch, the platform has also introduced a Sportsbook section on its official website, expanding its portfolio and bringing more choice to its growing customer base. With access to over 85,000 live events each month and more than 70,000 pre-match events across a wide range of sports, players now have even more ways to bet on what they love. Soft2Bet’s Canadian brand invites all players to explore its standout online casino and the full spectrum of sports betting, all delivered through a fast, secure, and fully localised platform.
Since its debut at the end of 2024, ToonieBet has offered a fast, fair, and secure online casino and sportsbook experience, fully localised for Ontario’s vibrant gaming market. The Apple App and Google Play additions further enhance accessibility, bringing ToonieBet’s premium entertainment to players on the go.
Additionally, this milestone complements the operator’s recent partnership with the NHL’s Ottawa Senators, which made ToonieBet the Official Online Casino Partner of the team. The partnership includes in-arena branding, digital promotions, and fan engagement initiatives like social contests, allowing ToonieBet to connect with Ontario sports fans in exciting ways and offering chances to win team merchandise and tickets.
Yoel Zuckerberg, Soft2Bet’s Chief Product Officer, said: “As Soft2Bet continues our rapid growth, we are excited to provide Ontario players with access to ToonieBet’s sportsbook which is now available on the Apple App and Google Play Store, offering seamless access to a customised experience tailored for the province’s passionate gaming community.”
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