Nearly two months into free agency since its start on July 1, only a few players remain available on the market. Among them is a former No. 2 overall draft pick with a strong connection to the Toronto Maple Leafs. According to a recent TSN report by Dave Feschuk, the Maple Leafs are contemplating a reunion with forward James van Riemsdyk as they look to enhance their left-wing depth. On August 26, TSN’s “First Up” featured analysts Aaron Korolnek and Feschuk discussing the potential return of van Riemsdyk to Toronto. Feschuk noted, “The Maple Leafs are reportedly keen on strengthening their left-wing position, which makes sense given their current roster and the absence of Nick Robertson, who remains an unsigned restricted free agent. James van Riemsdyk is available, and a reunion could be a real possibility.” Van Riemsdyk, originally drafted by the Philadelphia Flyers in 2007, spent his first three NHL seasons with them before being traded to the Maple Leafs in 2012 for defenseman Luke Schenn. He played 412 regular-season games for Toronto, scoring 154 goals. After returning to the Flyers in 2018, he most recently played for the Boston Bruins, where he had 11 goals and 27 assists in the 2023–24 season. Sportsnet hockey insider Elliotte Friedman mentioned in his August 25 “32 Thoughts” column that the Maple Leafs are looking to strengthen their left-wing depth, suggesting that something might be brewing in that regard. Daily Faceoff currently lists van Riemsdyk as the top remaining free agent as of August 27.