For example, Chicago supposedly lost money last year but the Wirtzes would make a fortune if they decided to sell. I don't know what they bought the team for way back when, but the appreciation has likely been in the hundreds of millions.
Chicago is an interesting & somewhat unusual case. "Dollar Bill" Wirtz claimed to have lost $191M between 97-07, $31M in the 06-07 season alone. Bill's father Arthur was a minority partner in Detroit with James Norris, who had bought the old Chicago Stadium in 1936; acquiring the Black Hawks in 1952 under puppet owner by proxy only (Tobin) for very little. Detroit was gifted to Norrises' daughter initially, then given to Bruce Norris, with future NHL President John Ziegler acting as Council & VP.
Bill Wirtz was appointed VP in Chicago, overseeing the revival of the franchise (Hull, Makita, SC etc) & President by 66. Over the intervening decades, vilified by the Black Hawks faithful for everything from the Esposito trade to Boston, Hulls' jump to the WHA, to letting guys like Belfour, Hasek, Chelios & Roenick walk getting cheaper replacement parts or nothing back in return. Much of the familys wealth is tied up in liquor distribution (as in bootleggers & associates of Capone in in the 20's) and real estate holdings, very wealthy, which made it hard to understand the mans parsimonious ways.
The original "Madhouse on Madison" was demolished in 94, Wirtz & Jerry Reinsdorf building, owning & managing the United Center ever since, home to the Bulls & Blackhawks, one of the largest & most lucrative arenas' on the planet. Merchandise sales, including retro Black Hawks & "Madhouse" gear continue to go through the roof, sellouts the norm as the teams fortunes improved, which including standing room can top out at 22,000+ for hockey. Concerts, conventions, special events etc combined with concessions including parking, sponsorships, state & city tax breaks etc etc etc & you've basically got yourself one giant cashbox in sports crazy Chicagoland the likes of which I would just have to suspect would push it all well into if not past MLSE territory in terms of value.
As a privately held company, Wirtz/Reinsdorf are under no obligation to report the "real" revenues & purported losses, though based on Reinsdorfs track record with the Bulls in squeezing out guys like Jordan and his manipulations with the Cubs in Illinois & Arizona; Wirtz Sr.'s well documented frugality, pretty hard to buy into the publicly stated numbers in terms of losses. The NHL receives 50% of the gate (based on regular season pricing) for all Playoff Games from every team participating, but still, absent regular season payroll & including the bonuses many players receive from the teams & their individual playoff performances, including Vezina, Smythe & other awards that if won means cash bonuses & better contracts next time their up for negotiations, you'd really have to be an idiot to buy the guff specifically in Chicago as to so much red ink being bled. I sure dont.
So, using Chicago as the model, as many of the leagues teams do, you then have to really start wondering about a whole bunch more of them, a lot if not most privately held & run with no obligation to report their true financials'. Like John Ziegler's hilarious pie-charts of 92 & overhead projector presentations using celluloid plastic spread sheets written in crayola, it sure looks tasty & palatable, Im sure it tastes good if you lick it upon conclusion & you'd likely get a pretty decent buzz off it all, but just dont swallow.