Frustrated Steve Apostolopoulos withdraws bid to purchase Senators

OTTAWA -- And then there were two. Three, at the most.

Any way you look at the Ottawa Senators franchise sale marathon, the number of bidders is whittling down and the process of getting closer to the end result has not always been pretty. There has been carnage.

On Friday, Toronto businessman Steve Apostolopoulos informed the selling parties (Galatioto Sports Partners, the NHL and the Eugene Melnyk estate) that he is withdrawing his bid to purchase Ottawa’s NHL club.

A source confirmed the Postmedia story that Apostolopoulos grew frustrated with the back-and-forth wrangling over bids and was pulling out.

As one source said, “the goalposts kept moving.”

The withdrawal of Apostolopoulos is stunning because it is widely believed he was the top bidder, with a pitch said to be above $1 billion USD. Apostolopoulos had already bid $6 billion in a failed attempt to buy the NFL's Washington Commanders earlier this year.

Andreas Apostolopoulos, Steve’s father, once owned the Pontiac Silverdome, then home to the NFL's Detroit Lions.

Never say never with this Senators ownership story. There is always the remote chance the sales team circles back with Apostolopoulos to return him the mix. But the same was said of the Remington Group, featuring actor Ryan Reynolds as the face of the bid, when they walked away from the process about a month ago. To this point, there has been no sign of Remington/Reynolds reconsidering.

And there is this: It is getting late in the game to be circling back. Those involved in this long and eventful sale hope to have it wrapped up in the coming days.

If Apostolopoulos did indeed file the highest bid, it isn’t hard to imagine why he grew frustrated that the bid failed to land him the franchise as the process dragged on.

Rather than a quick resolution, the GSP investment bank — acting on behalf of the Melnyk estate, including Melnyk’s daughters, Anna and Olivia — has opted to keep all of the bid groups engaged and haggling over bids and other details, in order to drive up the bid price. The NHL naturally approves of the tactic because it raises the bar on the value of league franchises in the future.

Of course, squeezing a lemon for all it is worth can come with risks. Such as a squirt of lemon juice in the eye. That is a bit of what the withdrawal of Remington and now Apostolopoulos must have felt like to the sellers.

Nevertheless, left in the running are two serious groups from Toronto — Michael Andlauer, who has a connection to the NHL as a part-owner of the Montreal Canadiens; and brothers Michael and Jeffrey Kimel, who were once partners in the Pittsburgh Penguins ownership group.

The Kimels have brought the Ottawa-connected recording star The Weeknd, of Scarborough, Ont., into their bid.

Neko Sparks, a Los Angeles-based producer, heads the other remaining bid, along with a host of celebrity backers, including rapper Snoop Dogg. Sparks has a vision of bringing to the NHL the most inclusive and diversified ownership group the league has ever seen. But there have been questions about the ability of the Sparks bid to bring to the table the financial resources to keep pace with the frontrunners.

Those frontrunners are down to two, now, which just might expedite the finishing chapter on a sale process that began seven months ago, in early November. Melnyk died in late March 2022.

To be fair to those involved, this is a complicated sale involving not just the sale of the hockey team but a chance to build a new arena for the Senators, closer to the core of the National Capital Region. There will be other real estate opportunities connected to the arena building and there is a large tract of land in Kanata on which the Canadian Tire Centre, Ottawa’s 27-year-old arena, sits.

The new owners will have to sort out existing team finances, including a large measure of debt that has been associated with the franchise since Melnyk bought the team in 2003.

Add in the fact that Anna and Olivia Melnyk would like to retain a 10 per cent equity in the new ownership and you get the picture — this is a complex deal that just might come to an end soon.

On the eve of the Stanley Cup Final last Saturday, NHL commissioner Gary Bettman said he felt the Senators sale was moving forward and that we could “expect a very good outcome in the next few weeks.”

The hope is that Bettman was trying to get everyone, fans included, to lower their expectations of the ownership transaction being imminent.

It is likely to conclude the moment we all take our eyes off the ball.