The trade rumor mill will run, and nothing will stop it. Not even the exclusion of the Detroit Red Wings from Phil Kessel's eight-team trade list — courtesy of a modified no-trade clause — can stop the talk about Ken Holland and Kyle Dubas hypothetically kicking this tire.
#81 / Forward / Toronto Maple Leafs
Oct 2, 1987
The first question that has to be answered is why Toronto would even want to trade Phil Kessel in the first place. Forget, for a moment, all the talk of a "scorched earth" rebuild that came about during the season from Brendan Shanahan. Toronto is in about as perfect a position as can be for leveraging a potential Kessel trade.
The Maple Leafs don't need to trade Phil Kessel. You may be wondering what Toronto would want in a five-time 30-goal scorer right as they're officially embarking on a rebuild. Even if Kessel is past the typical peak production years of a forward, this is still a player that is a pretty safe bet for 20 goals and 50 points for a few more seasons. While Toronto still has him, Kessel serves as an effective stopgap on the top line. He slots in and takes the toughest minutes so that the Maple Leafs can more effectively integrate younger players into the lineup by giving them easier minutes. While Kessel is still a top-line winger for Toronto, no one needs to be thrown into that role when it will probably be way over their head.
Better yet, if Kessel's career production arc turns out favorably for Toronto, he could even see the team to the end of the rebuild and be a valuable depth piece for a deep playoff run. Kessel will be 28 years old when the puck drops on next season, so it's not out of the realm of possibility that he becomes a 33- or 34-year-old third-line winger capable of producing 10-15 goals in those seasons.
If there's one thing that the Edmonton Oilers have taught us from the last decade, they can't expect to rebuild their way to success if there's not a quality veteran presence to guide the youngsters. I know some of you are probably rolling your eyes at the notion of Kessel as "quality veteran presence," but this is one of a few players who suffered that incredible Game 7 loss against the Boston Bruins in 2013. Kessel had four goals and six points during that series. So while Kessel would fetch a hefty return, there's still value in hanging on to him for another year or two until another player is ready to take Kessel's current role on the top line.
The obvious benefit to trading Kessel now, as previously stated, is that it maximizes his potential return. For Toronto to actually get that return, however, some team is going to have to pony up the assets to make Toronto want to pull the trigger on the deal.
The Maple Leafs are going to want draft picks and prospects. On the draft pick side of things, the Red Wings have a pick in every round this year except the second, and a pick in every round next year except the third. Toronto's going to want this year's first-round pick. They'll also obviously want next year's first-rounder, but that may be a non-starter from the Red Wings' side of things. So far, we're left with this year's first-round draft pick.
What prospects would add value to the deal? Remember that while Kessel is a perennial goal-scorer, he is on the downtrend of that part of his career. There's a risk that giving Toronto an Anthony Mantha or a Teemu Pulkkinen means giving them a perennial 40-goal scorer while we end up with a guy who used to score 30 goals regularly, only to barely hit 20. But it's a risk that has to be taken to add value — and not just bodies — to the deal and make the Maple Leafs want to pull the trigger. They're the ones with the leverage in this situation.
So we're left at Phil Kessel for the 19th overall pick in 2015 and one of Anthony Mantha or Teemu Pulkkinen. I'd bet that if Dubas were a more veteran general manager and had more familiarity with Holland, he'd hang up the phone right there, and understandably so. But for the Red Wings at that point, it already feels like mortgaging the future in giving up two valuable assets for a scorer that likely won't be the missing piece that makes the team a contender.
That doesn't even consider the other type of asset — a young, legitimate NHL player — that Detroit would need to offer to close the deal.
Yes, teams have to give to get in trades, but with the way this hypothetical negotiation has started, it doesn't seem worth pursuing any further for either party. Toronto wants more, and Detroit would be making their organization, if not next year's team, worse in the process if they offered more. And even if they do improve next year's team, that improvement will likely fall short of making the Red Wings Stanley Cup contenders. And even if they manage to woo Toronto with an acceptable trade package, Kessel likely nixes the deal because Detroit's not even on the eight-team list.