Many question whether Green - squarely in the crosshairs of activist investor William Ackman - is ruthless enough to overhaul the storied railroad to make it more efficient and profitable.
A CP lifer who is uniformly described as a decent, kind and just a plain nice guy, Green has largely stayed out of the ring during the fight of his corporate life.
The native of tiny Stephenville Crossing, Newfoundland, has declined media interviews and public presentations, and has conducted his campaign to keep his job by meeting with CP's shareholders behind closed doors.
It's a low-profile campaign that mirrors Green's management style during his five years at the top of Canada's second-biggest railroad.
But events have forced a change of tack by the 55-year-old Green. On Tuesday, CP will host an open meeting in Toronto to provide more details to shareholders on how it plans to make the country's No. 2 railway more efficient. In a rare public forum, Green will take center stage to counter the arguments put forth by the man who wants him to be sacked.
Ackman, whose Pershing Square Capital Management hedge fund has a 14.2 percent stake in CP, wants to replace Green with former Canadian National Railway boss Hunter Harrison, a plain-spoken Memphis native who promises to shake up the company culture in a push for productivity.
The showdown will come at CP's annual shareholders meeting on May 17.
"It's almost stereotypically Canadian versus U.S.," said independent railway analyst Tony Hatch, who has followed the sector for 25 years.
"The U.S. cowboy comes in very self-assured, and willing to share that with you, versus a more reticent, polite, nice - not that these are bad things - Canadian model."
The board at CP, which completed the first railway link to Canada's Pacific Coast from the more populous East in 1885, has bristled against what it calls Ackman's vague plan for improvement. It has backed Green and his remedy for fixing what is currently the worst operating performance among North America's Big Six railroads.
CP's operating ratio - the percentage of revenue needed to operate the railway - stands at 81.3 percent. CN, which made many of its efficiency gains under Harrison, has a 63.5 percent operating ratio, the best in North America.
Green, married for 30 years and father of two adults, has promised to reach 70 to 72 percent in 2014, while Harrison pledges to hit 65 percent by 2015.
Ackman, who wooed CP investors at a well-publicized Toronto town hall meeting in January, plays up Harrison's legendary corporate turnarounds, the result of a heavy-handed, detail-oriented approach.
Green, on the other hand, faces challenges in overhauling CP because he is an insider, said Trains magazine writer Fred Frailey.
"I think part of him is very proud of Canadian Pacific's role in Canadian history and he's interested in preserving that," said Frailey, who has covered the industry for 34 years.
"So it's tough. I just don't think he's been willing to be ruthless enough in terms of changing, I guess you'd call it the good old boy culture, particularly in the operating department."
Stepped Up
Reached for comment, CP Chairman John Cleghorn repeated that Green and his plan to improve efficiency have the board's full support.
"CP has changed. Fred led that change. We have a multiyear plan that is working and delivering results," he said in a statement.
Green, who joined the railroad in 1978, has said the 130-year-old company will not compromise principles for efficiency gains. Safe railways are cost-efficient and built on partnerships with suppliers and customers, he told Vancouver's Board of Trade.
Some say that Green and CP, which is heavily exposed to a single large customer in miner Teck Resources Ltd, have scored better on customer care than CN.
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