clock menu more-arrow no yes mobile

Filed under:

The Leafs Should Follow the Chicago Model (Not THAT One)

One team in professional sports can sympathize with the Leafs' recent struggles. Now, built on a similar plan to the one in Toronto, they're thriving.

Matt Marton-USA TODAY Sports

Sports, the old saying goes, is a copycat game. Teams look at other teams that have success as a model that should be imitated.

The problem with this, however, is that no two situations are alike. No two players are alike. There are so many variables on a team-to-team basis that it's hard for one team to simply follow a singular rebuilding structure. Sure, a team can hit home runs on top picks as the Blackhawks and Penguins did, but they also need to hit singles and doubles on their later round picks, as well as with trades and free agency. A team may also need only one top draft pick if they have a strong development system and make opportunistic trades, as the Kings did. Perhaps you take the slow path to rebuilding with a team of young prospects, while adding solid veterans to fill holes, as the Panthers have.

There's one team, however, to which the Leafs are eerily similar. They don't play hockey, but they have a similar history to the Leafs. They're also the most dominant team in their sport right now.

It's weird to even put in writing, but it's true: the Chicago Cubs are (almost) the culmination of what the Leafs should aspire to be in the rebuild.


I get that baseball is not hockey. Hockey is a much more fluid sport, less dependent on individual performance. Baseball has no salary cap, which has an impact on how decisions are made between the two sports. But, put that aside, and the similarities are telling.

The Cubs need no introduction to most sports fans. The team has long been the symbol for continuous futility in baseball. The Leafs' long Cup drought has nothing on the Cubs, who have not won a World Series since 1908, nor even made a World Series since 1945.

The Leafs and Cubs also are similar in having a recent history of playoff futility (three postseason appearances, and just one series win, for the Cubs in sixteen seasons from 1999 to 2014) and heartbreaking collapses when they do qualify (Steve Bartman will live in infamy as a much more notable "It Was 4-1"). They even have similar cursed figures in their lore: the Cubs had the curse of the billy goat, while the Leafs had Harold Ballard, who is arguably more evil and subhuman than a goat. I give the Cubs the slight edge on that last one.

But, enough about what both teams have had go horribly wrong; let's talk about what they're doing right. Both teams have built their teams in an eerily similar way:

  • Both teams boast a front-office structure consisting of a veteran executive experience and young analytical whiz-kids. Their President, Theo Epstein, and GM, Jed Hoyer, have worked in MLB front offices since 2002, but started at a young age (both were 28 when hired). The Leafs have that combination of management experience and analytical youth, but it's much more pronounced (Lou/Dubas).
  • Both teams worked hard to get a big fish behind the bench to kick-start their rebuild, and succeeded. In the 2014 offseason, the Cubs hired Joe Maddon, the long-time Tampa Bay Rays skip and two-time AL Manager of the Year. Maddon activated an opt-out clause in his contract to leave Tampa; he became the Cubs manager within three weeks. It took Toronto about the same amount of time to land Mike Babcock at the close of the Red Wings' 2014-15 season.
  • The Cubs roster boasts a trio of young prospects drafted by the team early in the 1st round: Javier Baez (9th overall, 2011); Kris Bryant (2nd, 2013); and, Kyle Schwarber (4th, 2014). Those selections are eerily close to where the Leafs have drafted Nylander (8th, 2014) and Marner (4th, 2015), and are likely to draft Auston Matthews with this year's 1st overall pick.

The Cubs are a few years ahead of the Leafs in their rebuild. Their 2012 and 2013 seasons were "bottom-out" years comparable to the last couple of seasons the Leafs have had. They were 61-101 and 66-96, respectively, and played out rebuilding years to angle for high draft picks. Their next season in 2014 was still not great- they were 73-89- but progress was made, and rookies such as Baez and Bryant made their debuts.

Last season was their breakout year. Just three years removed from their "rock bottom" 2012 season, they stormed to 95 wins and made it to the NLCS. This season, they're 28-10, outscoring their opponents by 100 runs already, and undoubtedly the best team in baseball right now.

Whether the Cubs can sustain their early season success and break their 108-year World Series drought remains to be seen; there's still a lot of baseball left to be played. That said, the meteoric rise of baseball's "lovable losers" gives the Leafs a blueprint of success.

Again, baseball and hockey are (obviously) different sports. It's hard to extrapolate exact things from one and impose it on the other. The key here is to look at some of the basic lessons the Cubs can teach the Leafs about rebuilding.

(1) Don't Fear the Reclamation Project

On July 2, 2013, the Cubs traded starting pitcher Scott Feldman and backup catcher Steve Clevenger to the Baltimore Orioles. The 47-36 Orioles coveted Feldman to shore up their starting rotation, and the return didn't seem so bad for them. Going to the Cubs was reliever Pedro Strop, and a 27-year old pitching prospect.

The prospect was labelled a disappointment in Baltimore. While he projected to be a No. 3 starter, he was a 20-25 starter with a 5.46 ERA with the Orioles. He bounced between AAA and the Majors frequently. At best, people said, the Cubs could hope for him to be a solid mid-rotation player. But the Cubs saw potential and hoped a change of scenery would benefit the player.

That player's name might be familiar to you: Jake Arrieta, winner of the 2015 NL Cy Young. Last year, he was 22-6 with a 1.73 ERA. He's somehow even better this year: 7-0 with a 1.29 ERA. And all this cost the Cubs was a pending UFA and second-string player.

A turnaround like Arrieta's is pretty improbable in sports, so to assume the Leafs could magically acquire the hockey equivalent of that is unfathomable. But it goes to show you that it might be smart to buy low on a player with unrealized potential. A change of scenery might be beneficial sometimes.

If the opportunity arises for the Leafs to acquire a reclamation project with upside, it's worth a shot for the right price. Teams won't command much in return. At worst, the player is a bust and you eventually part ways without being worse off in the long run. At best, well.....y'know.

(2) Free Agency, Done Right, Won't Hurt the Rebuild

When we talk about the Leafs looking to acquire a big-name free agent, there is some notable cringing and pearl-clutching. People are hesitant to add a piece that they fear will "rush" the rebuild. But will it?

The Cubs provide a good precedent here. In 2014, the Cubs finished the season 73-89, last in the NL Central and third-last in the entire NL. But their trio of highly-drafted prospects was set to play their first full season in 2015, which gave rise to substantial optimism (see where I'm going with this?).

So, what did the Cubs do? Went out and acquired the biggest-name free agent on the market; that's what!

On December 15, 2014, the team introduced pitcher Jon Lester, whom they signed to a 6-year, $155 million deal with an option for a seventh year. A huge signing for a team that was, before then, in "rebuild mode."

Did this move jeopardize or "rush" the rebuild? Not really; the Cubs still have a young core to build around. It had no effect on their overall rebuilding process; it just made them a better team ahead of schedule.

While the NHL and MLB are different leagues in that the former has a salary cap, the Lester signing is a valuable lesson into the long-term fit for a UFA signing. Lester came in with high expectations to be the team ace. The bad news is that he didn't have his best season in 2015. The good news is that he was still good, and didn't need to be the best; he could slide into a capable No. 2 role behind Jake Arrieta.

What does this have to do with the Leafs? A similar thought on free agency. If you sign a top tier player, you will pay for their potential, but at worst, that player will still be very good. A very good player, coupled with a wise rebuild, is still an extremely good asset. If you do things the right way, you don't need a big-name free agent to be *the* guy, nor should he be. Being one of many core pieces is the ideal outcome.

(3) Your Homegrown Players Will Be Expendable

The one observation I have throughout this rebuild is to treat virtually every prospect, either in Junior or on the Marlies, as a "future piece." Whether drafted last year or five years ago, there is an assumption that a player will definitely come up through the system and remain with the team through their peak years.

Obviously, this won't be true for everyone. Some players just will never reach their potential, and will eventually part ways with the team. But the underlying belief is that others- the promising young prospects who do make it- will be with the team forever. Not always true.

In 2006, the Cubs signed a 16-year old Dominican named Starlin Castro. He made the Cubs roster in 2010, becoming their everyday shortstop. He was an All-Star for a rebuilding Cubs team in 2012.

Now, at 26, he is a New York Yankee.

So, what happened? He became expendable. He wasn't bad, but was replaced at shortstop by a younger, better option in Addison Russell. After a postseason appearance in 2015, it was time to make an upgrade. The Cubs did just that, trading Castro to the Yankees for a pitcher, but also signing solid veteran utilityman Ben Zobrist to fill the vacancy at 2B.

The Leafs will not be rebuilding forever (we should hope). At some point after the transition from rebuilding to contending, it will be time to make tough decisions. Some prospects once considered integral to the rebuild may not be as untouchable as previously contemplated. To take that next step, the Leafs will have to part ways with some down the road.

(4) Sell High On Veteran UFAs

The Leafs are already doing this, but while still in a rebuilding phase, this remains imperative, including with the higher end players on the team. In 2012, the Cubs traded longtime pitcher Ryan Dempster to Texas, for a return including pitcher Kyle Hendricks. Hendricks is currently the Cubs' 5th starter, while Dempster retired in 2014 and works in the Cubs' front office, so that worked out pretty well. That promising young shortstop Addison Russell I mentioned earlier? Acquired from Oakland in a 2014 trade for then-No. 1 starter Jeff Samardzija. Samardzija has spent the last two seasons in Chicago (with the White Sox) and San Francisco, and hasn't really lived up to the billing.

The Leafs are already carrying out this plan, so there isn't much more to add, but it goes to show the long-term benefits that you can reap from a team trying hard to push for a championship.

(5) Trust Your Inside Knowledge

The thing about some of the Cubs on the current roster is that they have a history with the people running the team extending past Chicago. Zobrist spent years in Tampa Bay under Maddon. First baseman Anthony Rizzo was drafted by Hoyer in Boston, then acquired by him in San Diego before being acquired by him again in Chicago.

The Leafs have a management team and coaching staff with links to other organizations: specifically, Detroit and New Jersey in the NHL, and London and Sault Ste. Marie in the OHL, and should exploit that knowledge to the benefit of the team. To be clear, this isn't to say that the Leafs should sign an overpriced depth player because Lou or Babcock liked his hustle way back when. This means that this inside knowledge can be used to either: (a) exploit a market inefficiency for an undervalued asset to which you are familiar (Rizzo); or, (b) use personal connections to add a solid asset to your team (Zobrist).


The Leafs, like the Cubs, have a lot of history, most of it bad. The Leafs are undergoing a painful rebuild, as the Cubs did, to work towards the same goal of eventually ending a championship drought. The 2016 Cubs may not do that, but it's probably the best chance that franchise has had in a long time to pull it off. Despite the difference in sports, there are some lessons that Leafs management can learn from how the Cubs went from laughingstock to contender.