Nolan Arenado and the Rockies are approaching a critical crossroads. At stake is nothing less than the direction of the franchise, hundreds of millions of dollars and the future of a once-in-a-generation third baseman.

The Rockies must decide if they are able — or willing — to offer a contract that would likely exceed $200 million and make the 27-year-old Arenado the backbone of the franchise for the better part of the next decade. Or they might determine that a long-term deal is unworkable and attempt to trade Arenado — this winter or next summer — and then deal with the fallout from their fans.

Arenado, who’s scheduled to become a free agent after the 2019 season, must determine if he wants to stay with the team that raised him, or abandon that security and chase his World Series dreams in a different market. Arenado has said only that his overriding desire is to play for a perennial contender, and that he expects to be a member of the Rockies when spring training opens in mid-February.

Matt Holliday — the seven-time all-star who began his career with the Rockies, was traded away, and then rejoined the team for the latter part of the 2018 season — said he doesn’t know if Arenado wants to stay or go. But he does offer some sage advice: Look both ways before making the biggest decision of your career.

Arenado, Holliday said, is going to make “crazy money” no matter what he does. But Holliday also cautioned that “a lot of younger players always think the grass is greener somewhere else, but that’s not always the case.”

Holliday called Arenado “baseball’s ultimate gym rat,” and as such, figures that Arenado’s perception of the Rockies will play a huge part in the third baseman’s decision.

“If he wants to stay in Colorado, then it must be someplace where he is comfortable with the management and the front office,” Holliday continued. “He has to have the confidence to where they are going to be able to give him a chance to win, year in and year out. Plus, he has to make sure he finds a place where he’s personally happy and can focus on the things he wants to focus on.”

Holliday knows what he’s talking about.

Ten years ago, the Rockies, unable to come to contract terms with Holliday, shipped the slugger to Oakland for closer Huston Street, left-handed starter Greg Smith and an uber-talented, 23-year-old outfielder named Carlos Gonzalez. Holliday played half a season with the A’s before he was traded to St. Louis. In January 2010, he signed a seven-year, $120 million contract with the Cardinals, with whom he played in two World Series, winning a ring in 2011.

There are striking parallels between the Holliday trade of 2008 and Arenado’s current situation.

During spring training of 2007, the Rockies offered Holliday a four-year, $72 million extension with a fifth-year club option for $12 million. In Colorado’s view, it was a seven-year deal worth $107 million when counting Holliday’s final two guaranteed arbitration seasons.

But Holliday and Scott Boras, his powerful, high-profile agent, viewed the numbers differently. They viewed salary arbitration as a separate issue, so, to them, the Rockies’ offer represented an $84 million free-agent contract without a no-trade clause.

“It was an incredibly hard decision for me,” Holliday recalled. “I was hoping the length of the contract would be longer. A four-year deal at age 27 was, quite honestly, the most disappointing part of it to me. The way it was presented to me, it was sort of a non-negotiable kind of deal. It was their best offer and their only offer.”

Holliday stressed that he loved Colorado and hoped negotiations would continue and that he might find a way to stay in a Rockies uniform.

“It wasn’t because I didn’t want to be part of the organization,” he said. “There was still hope on my end that we could revisit things and I could end up staying in Colorado. I wasn’t trying to get out of there. There was not anything the organization was doing, or not doing, that made me make my decision (not to sign the contract). I loved Colorado. I love the people there, then and now.”

Dan O’Dowd, Colorado’s general manager at the time, has a different take.

“We thought we had a contract in place with Matty in spring training,” recalled O’Dowd, now an analyst for the MLB Network. “Everybody in the organization felt like Matt, along with his wife, Leslee, and his family, represented everything we wanted for our franchise.

“We thought he was a cornerstone guy for us as we went through our rebuild to the World Series. We were sure Matt had a great career ahead of him.”

O’Dowd said the Rockies made a “very aggressive run” at Holliday, but also knew that Boras did not typically like his clients to sign contracts prior to free agency. So when the offer was rejected, O’Dowd and his front office turned the page.

“We knew at spring training that no matter what efforts we made that Matt was going to be a free agent,” O’Dowd said. “No matter what efforts we made, we would not have the opportunity to extend him — in any way, shape or form — other than competing for him on the open market.

“We just made a decision at the end of the (2008 season), that if the right opportunity came along and was a really good fit for us, then we felt it was in the best interest of our organization to move on from Matt.”

O’Dowd added that the blockbuster trade not only netted the Rockies a genuine closer in Street, as well as Gonzalez’s tantalizing talent, but also enabled the club to avoid “the constant tugging, pulling and distraction” of Holliday’s contract status as the 2009 season loomed.

Current Rockies general manager Jeff Bridich, who worked under O’Dowd from 2005-14, has been relatively tight-lipped about Arenado’s future in Colorado.

“There’s not a perfect timeline or a specific timeline, but we’d love to have him here, and he knows that,” Bridich said earlier this month. “We’ll see what happens … We expect him to be on our team next year.”

Bridich recently discounted national reports that the Rockies are waiting to see what kind of contracts current superstar free agents Bryce Harper and Manny Machado land before deciding on what to offer Arenado.

But, realistically, can the Rockies compete with baseball’s big spenders and hold onto Arenado for the long term? In 2018, Colorado’s payroll rose to $143.9 (13th in the majors) and Bridich sees that trend continuing.

“We intend to have responsible growth of payroll and of the overall operation,” he said. “Success begets more growth and that’s a great thing. We are still in that mindset.

“As payroll relates to Nolan or anybody else on a large contract, I think you have to take those things as they come. We don’t know exactly what those contracts will look like. Whether it’s Nolan or somebody else on one of those huge contracts, it’s not like we automatically say no to it, by any means.”

Bridich added: “That’s my way of saying that we are going to stay open-minded, and it’s not like we categorically eliminate those types of situations from our future. But I do think we are appropriately cautious.”

O’Dowd said he’s not in a position to predict Arenado’s future. He does, however, think that the landscape in baseball has changed significantly since he was a GM, making it more difficult to pull off trades like the one he engineered a decade ago.

“With all of the data now available, young players are valued at a level never before seen in our game,” he said. “Organizations understand the long-term financial impact of what the young players are actually worth. So to trade impactful young players in exchange for very little control of a veteran player, whoever he might be, it doesn’t happen often. There is just a different set of dynamics at play.”

That could mean that when it’s all said and done, the decision will ultimately be in the hands of Arenado and his agent, Joel Wolfe. Holliday can relate, and also commiserate, with the decision Arenado faces.

“It’s a little bit scary thinking about going somewhere else, especially when you have been someplace for five-plus years,” Holliday said. “You try to listen to the people you hire and you try to listen your family and you try to make the best decision.

“It was a very difficult situation for the six months from the time I turned down the contract to the time I was traded. You want it to work out with where you are, but you also owe it to yourself to see what your market value is as you get closer to free agency. It’s a tough spot for players and it’s a hard decision. One of the hardest you’ll ever have to make.”