Most notably this summer Tyler Bertuzzi was a victim of the flat cap. Bertuzzi was expected to sign a massive contract but instead settled for a 1-year deal with the Maple Leafs. While Bertuzzi settled on a short team deal it turns out that both he and the Leafs were working on a longer term deal but were unable to make the financials work.
According to Elliotte Friedman though, it's very possible that the Leafs and Bertuzzi already have something in the works for January 1st. This would mark the first day Bertuzzi is allowed to sign and would align perfectly with next year's raised cap. Friedman had the following to say on a recent radio appearance.
It's very possible that the Leafs and Bertuzzi already have a handshake deal in place that could see Bertuzzi remain in Toronto for a much longer term.
This would be a great move for the Leafs, who definitely need Bertuzzi's edge and toughness.