On this day in 2016, the Leafs trade Dion Phaneuf in blockbuster trade with Senators

The expectations turned to disappointment despite Phaneuf consistently finding his name on the score sheet and two 100-plus point seasons (2013-14 144 points, 2014-15 108 points). As the Leafs continuously struggled throughout the years, the disappointment grew, and when Phaneuf was finally sent to Ottawa, the market wasn’t overly surprised.

“He was as classy as anyone could possibly be,” former Leafs general manager Lou Lamoriello told The Toronto Star’s Rosie DiManno after the news of the trade. “I just expressed to him how much I appreciate what he’s brought to the things we’ve tried to change and how supportive he’s been.”

Phaneuf recorded 45 goals and 196 points during 423 games with Toronto. In Ottawa, things were much quieter for the 30-year-old blueliner. He wasn’t in a top defensive pairing, he wasn’t playing over 25 minutes a night, and he certainly wasn’t producing what he was back in Toronto, with the exception of a 100-point season in 2016-17. After three seasons, 13 goals, and 54 points, Phaneuf was again traded to the Los Angeles Kings.

The other parts of the package heading to Ottawa were Bailey, Donaghey, Frattin, and Rupert. However, Bailey and Frattin were the only two with minor NHL experience. At the same time, Rupert and Donaghey never saw a regular-season NHL game.

Frattin was the 99th overall selection by the Leafs in the 2007 draft; he joined the club for his debut in 2010-11 but only made one appearance. The following season was more promising, and the forward saw 56 games, recording eight goals and 15 points. After 25 games with the Maple Leafs in 2012-13, he was traded to the Los Angeles Kings, then months later to the Columbus Blue Jackets. He made his way back to Toronto in 2014, appearing in nine games, but following the trade, he never played a game in the Senators’ iconic sweater.

On the other hand, Bailey–who went undrafted–signed as a free agent with the Leafs in 2015 but only appeared in six games. When he moved to Ottawa, he appeared in seven games before signing as a free agent in 2018 with Slovan Bratislava in the Kontinental Hockey League.

The players Toronto received in exchange had far more NHL experience, although none lasted in the organization.
Cowen was a prospect who showed significant promise. However, he never dawned a Maple Leafs jersey and, due to injury, was bought out. Greening played 30 games for the Maple Leafs, scoring seven goals and 15 points. In the 2016-17 season, he was primarily placed on the Toronto Marlies, the club’s American Hockey League affiliate, where he played for the following two seasons.

Lindberg also appeared in six games for the Leafs during the 2015-16 season, but he also wound up with the Marlies. He was eventually a draft pick to the Vegas Golden Knights in the NHL expansion draft but was traded a year later to the Pittsburgh Penguins. From there, he continued to play the role of a trade piece back to the Senators before heading to Sweden.

Like Lindberg and Greening, Michalek played only a handful of games for the Maple Leafs, scoring two goals and eight points throughout two seasons.

The second-round pick they acquired at the 2017 draft landed them defenceman Eemeli Rasanen; he too never wore the Maple Leafs sweater.