Within the past calendar year, Tomas Kaberle has played for four teams and six coaches. After leaving Toronto, he was generally pretty ineffective in Boston, failing to ignite their powerplay . But he still managed to help the Bruins win a Stanley Cup (however inconsequential his contribution may have been). This season he continued his disappointing play in Carolina before finding himself in Montreal. It has been as rough as any year highlighted by a championship ring could be.

Kaberle ’s replacement in Toronto, John-Michael Liles , a player who in a way was a part of the initial trade with Boston (the conditional second rounder Boston sent the Leafs was shipped to Colorado for Liles ) has integrated into the Leafs lineup and filled the role vacated by Kaberle seamlessly.

Liles forms the first defensive pairing on the Leafs’ powerplay and has helped ignite a once dormant unit that was 22nd in the league last season. With Liles quarterbacking the man-advantage, Toronto sits 3rd in league, helping propel the Leafs to a top-10 offense.

Liles has 21 points on the year, which before sustaining a concussion was one more than Phaneuf, and has accumulated 10 of those on the powerplay . He was advertised as a Kaberle-lite when the Leafs acquired him, but considering the way Kaberle has played recently you wonder who the knockoff really is.

As a bonus, the Indianapolis native has provided a steady influence on the back-end, playing a pretty solid game and rarely showing the defensive deficiencies that Kaberle frequently did during his later “I don’t give a shit” years.

Liles is in the final year of a contract that pays him $4.2 million, after which he becomes an unrestricted free agent.

Liles has been everything the Leafs wanted when they acquired him.

Of course, his current injury is of a concern, especially since he hasn't started skating with the team,

but Toronto must still decide whether he is in their long-term plans.

Signing him to an extension would cost at least what he’s making now, likely something closer to $5 million a season. If Kaberle can negotiate a three-year deal worth $4.25 a season after a dreadful stint in Boston, then Liles can surely receive at least a modest increase on his current salary.

The problem is the Leafs don’t have a lot of money coming off the books next season. Technically, they have close to $15 million, but Nikolai Kulemin , Matt Frattin , Keith Aulie and Cody Franson are all restricted free agents looking for raises. More importantly, Mikhail Grabovski becomes an unrestricted free agent, and with the lack of quality centres on the market can probably command a figure between $4-5 million a season.

Re-signing Liles might mean Grabovski is let go in favour of a younger, cheaper option, such as Joe Colborne who would only come with a cap hit of $1.1 million.

Or do the Leafs let go of Liles and hand his role to a younger player such as Jake Gardiner? Giving the role of the primary powerplay quarterback to a sophomore would be a gamble, but Gardiner has surpassed even the most optimistic expectations this season. The Leafs could also slot Tim Connolly on the point, which he has played at times this season and previously in Buffalo.

If the option is between keeping Liles or Grabovski , the Leafs would be better served keeping the latter. Both quality centres and puck-moving defenceman are hard to find, but the Leafs have more depth on the backend, making Liles’ hypothetical departure more palatable.

And if Liles is not part of the Leafs long-term plan, it’s important the Leafs try to supplement their rebuild by trading Liles at this year’s deadline.

It would be a gutsy move to make. The Leafs are likely a team that will fight for the final few playoff spots for most of the season. Trading an integral part of the team’s immediate success would be a blow to the team’s playoff chances, but a return for Liles , who would potentially walk for nothing at the end of the season, would be the better move long-term.

Last season the Leafs did not miss a beat after trading both Francois Beauchemin and Tomas Kaberle . They called up Keith Aulie and played even better down the stretch without the two veterans. Expecting a similar return as the haul Burke received for Beauchemin is unrealistic, especially considering Liles is a UFA at season’s end, but the demand is always there for puck-moving defenceman.

But the Leafs were bad with Beauchemin , so even if they got worse it wouldn’t have really mattered. The Leafs are doing well with Liles . Wouldn’t trading him be the equivalent to waiving a white flag on the season?

Well, the Leafs once again have a deep blueline and could reasonably expect to remain competitive even without Liles . Once Mike Komisarek returns the Leafs will have two excess NHL-level defencemen sitting on the sidelines (or in the case of Keith Aulie , the AHL). Plus, Dave Nonis recently stated that AHL defenceman Jesse Blacker is close to NHL ready.

Of course, none of the excess defencemen have the puck-moving abilities of Liles (and really, Komisarek was only really passable playing with Liles ), and handing Liles’ duties to a player like Gardiner would be a lot considering Gardiner is already playing much more than he is accustomed to coming from college hockey.

However, the Leafs’ course of action may be determined by the trade market. If Burke has grander plans, such as packaging a younger defenceman and other prospects for an impact forward (Ryan Getzlaf alert), then Liles may have a long-term future in Toronto and the Leafs may explore an extension. On the other hand, this could also mean Liles is priced out of Toronto depending on the salary any potential incoming player is owed.

Or if the trade market is tepid towards Liles , offering merely something akin to a second-round pick, the Leafs would probably be better served keeping Liles , making a push for the playoffs, regardless of whether he is in the team’s long-term plans.

be made to think through that lens. The long-term future is more important than the short-term gain and must be placed ahead of it accordingly. However, the club needs to make meaningful strides towards the playoffs, and ending the long-standing drought with a playoff berth would be a positive for the team with potential long-term benefits as well.

What should the Leafs do with Liles?

There has definitely been no seller’s regret in Toronto.But these positives mean the Leafs have a dilemma.If he is in their long-term plans they must sign him to an extension - provided he is able to recover from his injury and return to form. If he isn’t in the team’s long-term plans do the Leafs trade him at the deadline or let him walk away for nothing at season’s end?The Leafs are still a rebuilding club and every effort mustJohn-Michael Liles’ tenure in Toronto has been nothing but positive, which only makes his future in the hockey hotbed even less certain.