You've probably heard the expression "bet on the jockey." The phrase originally referred to gamblers' preference to stake money in a horse race more on the track record of the jockey instead of the horse. It has also been extended to the investing world, with the idea that the likelihood of a stock's success strongly relies on the capability of the company's CEO.

How does the idea of betting on the jockey play out with investing in marijuana stocks? Here's a look at the CEOs of the top five Canadian marijuana stocks in terms of market cap -- Canopy Growth (NASDAQ:CGC), Aurora Cannabis (NASDAQ:ACB), Cronos Group (NASDAQ:CRON), Tilray (NASDAQ:TLRY), and Aphria (NASDAQ:APHA) -- and which of these "jockeys" might be most worth betting on.

Wooden blocks stacked in a pyramid with images of business people on each block.

Image source: Getty Images.

Canopy Growth's Mark Zekulin

Perhaps the most important thing for investors to know about Canopy Growth CEO Mark Zekulin is that he won't be at the helm for too much longer. Until a couple of months ago, Zekulin was co-CEO, sharing the top executive duties with Canopy Growth co-founder Bruce Linton. But when Linton was fired in July, Zekulin stated that he would lead the company only until a new CEO could be found.

Zekulin's background is in international law. He has been with Canopy Growth since the company began operations. Zekulin served as Canopy's president before being named co-CEO in June 2018. He helped lead the company to become the largest Canadian cannabis producer, overseeing all operations except for finance and information technology.

Aurora Cannabis' Terry Booth

Terry Booth co-founded Aurora Cannabis in 2013 and has served as its CEO since then. He led the company to grow rapidly through a string of acquisitions, including the 2018 buyout of MedReleaf. While those acquisitions have boosted Aurora's production capacity tremendously, they have also resulted in the company issuing a massive amount of new shares, diluting the value of its stock. Booth isn't apologetic about Aurora's approach, though, stating a few months ago that "if there's one thing I lose sleep about, it's our ability to supply the global demand for cannabis."

Prior to founding Aurora Cannabis, Booth was a serial entrepreneur. During his career, he has served as president and/or CEO of six companies, including Superior Safety Codes, which was named one of Canada's top 50 fastest-growing companies in 2011.

Cronos Group's Mike Gorenstein

Mike Gorenstein's background is in investment management. He was the vice president and general counsel for Alphabet Partners, where he managed a $900 million fund. Gorenstein looked for opportunities in the U.S. cannabis industry but ultimately turned toward Canada instead, co-founding Gotham Green Partners. Gorenstein's investment in PharmaCan led to him taking over as CEO of the cannabis producer in 2016, with PharmaCan becoming Cronos Group.  

The biggest success of Gorenstein's reign at Cronos Group so far is the partnership he forged with tobacco giant Altria. In December 2018, Altria announced that it was buying a 45% stake in Cronos for $1.8 billion. Although Cronos has lagged behind several of its peers in production capacity, Gorenstein's dealmaking has helped vault the company into the upper ranks in the industry.

Tilray's Brendan Kennedy

Tilray CEO Brendan Kennedy is another cannabis producer top exec with ties to the investment management industry. Kennedy is executive chairman and founder of Privateer Holdings, a private investment firm that's the majority shareholder in Tilray. He served as CEO of Tilray Canada since 2013 and became president and CEO of Tilray Inc. in January 2018.

Kennedy has been especially active on the business development front. He helped land a major partnership with Novartis subsidiary Sandoz to market medical cannabis products, first in Canada and then globally. He led Tilray to strike a deal with beer giant Anheuser-Busch InBev to develop nonalcoholic cannabis-infused beverages. Kennedy also guided Tilray to team up with Authentic Brands Group (ABG) to market and distribute consumer cannabis-infused products and to acquire North American hemp foods maker Manitoba Harvest.

Aphria's Irwin Simon

Irwin Simon founded organic and natural products company Hain Celestial Group in 1993. He led Hain Celestial for more than 25 years, with the company growing into a multibillion-dollar global enterprise. Simon was appointed as Aphria's chairman of the board in December 2018 in the midst of a controversy over allegations that the company drastically overpaid for Latin American acquisitions in a deal that lined the pockets of key insiders.

Following the resignation of Aphria co-founder and longtime CEO Vic Neufeld in January, Simon became the company's interim CEO. During his short tenure, Aphria has moved past the controversy related to its Latin American acquisitions. The company also achieved profitability, thanks largely to its acquisition in early 2019 of German medical cannabis and pharmaceutical distributor CC Pharma.

And the award for best CEO goes to...

Which of these men is the best CEO among the top Canadian cannabis producers? Mark Zekulin is on the way out at Canopy Growth, so it's pretty easy to mark him off the list.

Terry Booth has arguably accomplished the most as CEO, guiding Aurora to become the largest cannabis producer in terms of production capacity and the second largest by market cap. I also think that Cronos Group CEO Mike Gorenstein and Tilray CEO Brendan Kennedy have shown some impressive prowess in making deals that have put their companies on the map.

But if I had to bet on only one of these "jockeys," my money would be on Irwin Simon. Sure, Simon is only the interim CEO right now. However, Aphria hasn't talked much about its search for a new CEO. I wouldn't be surprised if Simon could be named permanent CEO.

What I like the most about Irwin Simon is that he brings a track record of building a successful commercial brand and a reputation for integrity. Even if he doesn't remain the CEO of Aphria, I expect that Simon will stay on as chairman of the board. He's just the kind of person that Aphria needed to right the ship, and my view is that he's doing a great job at doing just that so far.

This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.