{"id":798431,"date":"2026-07-13T05:16:18","date_gmt":"2026-07-13T05:16:18","guid":{"rendered":"https:\/\/www.newsbeep.com\/ca\/798431\/"},"modified":"2026-07-13T05:16:18","modified_gmt":"2026-07-13T05:16:18","slug":"the-maple-leafs-will-haunt-larry-tanenbaum","status":"publish","type":"post","link":"https:\/\/www.newsbeep.com\/ca\/798431\/","title":{"rendered":"The Maple Leafs will haunt Larry Tanenbaum"},"content":{"rendered":"

Open this photo in gallery:<\/a><\/p>\n

Larry Tanenbaum speaks as the Toronto Argonauts host a rally to celebrate their Grey Cup win, in November, 2022.Cole Burston\/The Canadian Press<\/p>\n

By any conventional measure, Larry Tanenbaum will leave Maple Leaf Sports and Entertainment later this year as a winner. <\/p>\n

The chair emeritus of the company that owns Toronto\u2019s pro hockey, basketball, football and soccer teams will depart with a $4.35-billion cheque for his 25-per-cent stake in MLSE from Rogers Communications Inc., along with championship rings from all the leagues, save one. <\/p>\n

That one missing trophy, the failure to hoist the Stanley Cup with the Toronto Maple Leafs<\/a>, is going to haunt an 81-year-old who has known success in everything else he\u2019s ever done in sports and business. <\/p>\n

Those who know Mr. Tanenbaum say the billions he will bank on the MLSE sale – in 1996, he spent just $21-million for his original 12.5-per-cent stake in the Maple Leafs – will have little impact on the lifestyle of an entrepreneur who already owns a Gulfstream G700 corporate jet and all the other trappings of wealth. <\/p>\n

Mr. Tanenbaum is leaving MLSE, reluctantly, with unfinished business, say those who know him. <\/p>\n

Rogers acquires remaining stake in MLSE from Kilmer Sports for $4.35-billion<\/a><\/p>\n

His low-key departure honours the legacy of his father Max Tanenbaum, an immigrant from Poland who built a steel and real estate business where his word was his bond.<\/p>\n

Shortly after the Raptors\u2019 NBA championship run in 2019, Mr. Tanenbaum said in an e-mail exchange that his overarching personal priority was winning a cup with the Leafs. Last week, he declined interview requests after announcing the sale of his MLSE stake. <\/p>\n

Mr. Tanenbaum has a tradition of winning in hockey that dates back to his college days. As student manager of Cornell University\u2019s hockey team, Mr. Tanenbaum picked up sweaty gear and booked travel for a team that won the 1967 NCAA championship. <\/p>\n

Ken Dryden, Cornell\u2019s goalie, a cup winner with the Montreal Canadiens and former MLSE executive, said in a 2004 interview<\/a> with The Globe and Mail\u2019s Michael Grange that Mr. Tanenbaum had \u201ca tough job. Guys that age aren\u2019t always the most respectful.\u201d <\/p>\n

That tough job at Cornell fed an interest in the business of sports that led Mr. Tanenbaum to start building his MLSE stake in 1996, after significant financial wins on the sale of paving and cable businesses.<\/p>\n

Andrew Willis: Rogers has the luxury of time as it reviews bidders on its sports assets<\/a><\/p>\n

Rogers and its former partner in MLSE, Bell parent BCE Inc., negotiated the right to buy out Mr. Tanenbaum back in 2012, when the two telecoms purchased a 75-per-cent stake in the sports platform from the Ontario Teachers\u2019 Pension Plan. The deal valued MLSE at $2-billion. <\/p>\n

In 2024, Rogers bought out Bell\u2019s stake in MLSE for $4.7-billion, valuing the company at $12.5-billion. <\/p>\n

The sale to Rogers announced last Monday, which is expected to close by the end of the year, values MLSE at $17.4-billion. In a report last week, analyst Maher Yaghi at Bank of Nova Scotia said in a report: \u201cRogers is underwriting a much higher sports asset value than investors assumed.\u201d<\/p>\n

Mr. Tanenbaum\u2019s massive gain on his investment in MLSE makes him a financial winner. But it doesn\u2019t complete his trophy case. <\/p>\n

The lack of drama around Mr. Tanenbaum\u2019s departure reflects planning on the part of MLSE\u2019s owners.<\/p>\n

All four Rogers siblings challenge executor compensation, including to Larry Tanenbaum, in mother\u2019s estate<\/a><\/p>\n

In 2012, Rogers, Bell and Mr. Tanenbaum struck an agreement on how to value the business if one or both of the telecoms wanted to buy him out. In part, this foresight reflected Mr. Tanenbaum\u2019s desire to avoid a repeat of the messy succession battle that played out in his extended family after Max Tanenbaum died in 1983. <\/p>\n

While the formula for buying out Mr. Tanenbaum was preset – it involved picking the average of prices submitted by multiple independent valuators – there was always speculation he and Rogers would disagree on terms. <\/p>\n

In the past, Mr. Tanenbaum had a sometimes frosty relationship with Rogers executive chairman Edward Rogers, who will soon own 100 per cent of MLSE. In a line, their uneasy partnership stemmed from the fact that for Mr. Rogers, business come down to numbers. <\/p>\n

Mr. Tanenbaum, while attentive to the bottom line, is a people person. After every Leafs\u2019 game he attends, he visits players in the locker room. Former MLSE chief executive officer Tim Leiweke joked one of his challenges was managing Mr. Tanenbaum\u2019s friendship with players, who were frequent guests at his home. <\/p>\n

Mr. Tanenbaum and Mr. Rogers were at odds on a number of decisions over the years, including a rumoured $12-million-a-year contract for former Raptors\u2019 president Masai Ujiri, who now runs the Dallas Mavericks, and MLSE\u2019s decision to pass on bidding for a WNBA team. <\/p>\n

Edward Rogers tries to deny payments to Larry Tanenbaum in dispute over mother\u2019s estate<\/a><\/p>\n

In 2024, Mr. Tanenbaum, through family-owned Kilmer Sports Inc., bought a WNBA expansion franchise, the Toronto Tempo, for approximately US$115-million. By May, when the team first tipped off, the highwater mark on the price of an WNBA team was up to US$325-million. <\/p>\n

Last Monday, when Mr. Tenenbaum announced his impending departure, there were no fireworks. In a poignant \u201cLetter to Fans,\u201d he said: \u201cAs I step back as an owner, as contemplated by a shareholders agreement entered into 15 years ago, I am extremely proud to leave this legacy of excellence, a culture of winning, and a family feeling among all our MLSE employees.\u201d<\/p>\n

Mr. Tanenbaum went on to \u201capplaud the accomplishments of Edward Rogers\u201d and thank fans for cheering \u201cthrough it all, from heartbreaking losses to euphoric championship wins.\u201d <\/p>\n

Part of the goodwill may reflect the fact that Rogers paid Mr. Tanenbaum about 10 per cent more for MLSE than analysts calculated the platform is worth, a $400-million boost. The numbers make sense for the telecom. <\/p>\n

Over the next year, Rogers plans to turn around and sell a minority interest in MLSE, plus baseball\u2019s Blue Jays and its media assets, to institutional investors at a valuation of $25-billion. Going into the process, the telecom is motivated to set a high bar for potential bidders by acquiring Mr. Tanenbaum\u2019s stake at a premium price. <\/p>\n

Sports will remain part of Mr. Tanenbaum\u2019s business after he leaves MLSE. In addition to the WNBA, he owns French soccer club AS Saint-\u00c9tienne. <\/p>\n

In June, Mr. Tanenbaum became the first Canadian investor in the Professional Women\u2019s Hockey League, or PWHL, which is owned by private equity fund manager TWG Global. In the press release to announce the deal, Mr. Tanenbaum said: \u201cHockey is in our DNA as Canadians, and that passion brought us to the PWHL.\u201d<\/p>\n

There is likely to be a day when Mr. Tanenbaum wins more hardware in the WNBA, PWHL and French soccer. <\/p>\n

But when the Leafs win their first championship since 1967, then as Mr. Tanenbaum said in his letter, he will just be another fan, sitting in the stands. <\/p>\n","protected":false},"excerpt":{"rendered":"Open this photo in gallery: Larry Tanenbaum speaks as the Toronto Argonauts host a rally to celebrate their…\n","protected":false},"author":2,"featured_media":798432,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[5],"tags":[901,888,902,879,877,903,45,49,48,876,895,896,891,878,875,46,549,295,894,887,914,880,881,893,889,890,884,904,885,909,910,912,907,911,905,908,882,898,899,714,897,906,865,61,900,892,886,883,913],"class_list":["post-798431","post","type-post","status-publish","format-standard","has-post-thumbnail","category-business","tag-alberta","tag-arts-news","tag-bc","tag-breaking-news","tag-breaking-news-video","tag-british-columbia","tag-business","tag-ca","tag-canada","tag-canada-news","tag-canada-sports","tag-canada-sports-news","tag-canada-trafficcanada-weather","tag-canadian-breaking-news","tag-canadian-news","tag-economy","tag-education","tag-environment","tag-federal-government","tag-foreign-news","tag-globe-and-mail","tag-globe-and-mail-breaking-news","tag-globe-and-mail-canada-news","tag-government","tag-life-news","tag-lifestyle","tag-local-news","tag-manitoba","tag-national-news","tag-new-brunswick","tag-newfoundland-and-labrador","tag-northwest-territories","tag-nova-scotia","tag-nunavut","tag-ontario","tag-pei","tag-photos","tag-political-news","tag-political-opinion","tag-politics","tag-politics-news","tag-quebec","tag-sports-news","tag-technology","tag-travel","tag-trudeau","tag-us-news","tag-world-news","tag-yukon"],"_links":{"self":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/posts\/798431","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/comments?post=798431"}],"version-history":[{"count":0,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/posts\/798431\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/media\/798432"}],"wp:attachment":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/media?parent=798431"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/categories?post=798431"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/tags?post=798431"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}