Not sure about optics with Paul Rivett, it is a little perplexing.
But the deal itself is not a "sweetheart deal". If anything, Torstar's fairly/overvalued at these prices. There's cash, but also a lot of liabilities, AP, provisions, pension liabilties.
FCF in 2019 was ($9M) and ($20M) after capex. There's no indication that'll stop. They'll probably have to inject more working capital if the bleeding continues or accelerates, especially with this whole COVID situation. VerticalScope made $18M in 2019, maybe less this year, but has close to $145M in net debt, so equity is probably not worth very much. It's nowhere near the $100M that they're carrying it at on the books. If you adjust the balance sheets and net out liabilities, there's really not much equity left.
Also, advertising $ is going to take a big hit. Very few newspapers will survive and this is the Toronto Star, not NYT or WSJ.
It was a stupid investment to begin with, so they're lucky to get some money out.