There was a point, as Cashman later recounted, that he wondered if this would all blow up in his face. CC Sabathia seemed like he wanted to stay closer to his northern California roots. A.J. Burnett was hot and heavy with the Braves. Ownership wasn't convinced it needed to go get a big bat like Mark Teixeira's.
What if the Yankees had not doled out $423.5 million in checks? Would they have still been standing at the center of the new Yankee Stadium, piling in a pinstriped crush, without chasing down the top three free agents -- not to mention sweet-talking Andy Pettitte, who wound up winning all three clinching games in the postseason?
Money may not be able to buy you happiness, but it certainly put the Yankees in a better position to get there. Not only did Cashman's three big free agents all sign on the Steinbrenner dotted line, but they had wonderful seasons in helping the Yankees get to the promised land with their 27th World Series title.
"You throw a bunch of talent together, and some years the talent mixes together where it's combustible, where it creates chemistry and love and fight," Cashman said. "This team had all that. To beat the Phillies, you're going to need all that. It's been a tremendous year."
Having made it to the previous two postseasons with the Indians and Brewers, the third time was the charm for Sabathia, who went 19-8 with a 3.37 ERA in 34 starts for the Yankees after signing a seven-year, $161 million contract.
There was trepidation in leaving the comforts of the Bay Area for Sabathia, as Cashman tried to woo the left-hander in Las Vegas before jetting off undetected for a house call.
The caveat that the Yankees agreed to was this -- if Sabathia didn't like New York, he could opt out after the third year of the contract and try free agency all over again.
But Sabathia put down roots in the clubhouse and is building his dream home in Alpine, N.J., a short ride over the George Washington Bridge from Yankee Stadium.
"To be able to do it in the first year of this house, it feels great," Sabathia said. "From the first day of Spring Training, everyone came in and got along."
As he cradled his son on his shoulders in the wet celebration after Game 6 on Wednesday, one thing appeared clear -- Sabathia wasn't planning on being anywhere but with the Yankees.
"It's hard to do, but I can't say I didn't expect us to be here in this situation with all of these great players and experience that we have," Sabathia said. "It just feels good to get it done. This is a great feeling. This is what you play the game for. This is what, as a 3-year-old kid, you dream about."
Burnett was the next chip that fell into line for the Yankees, and while talks did progress with Atlanta, the allure of sliding in as the No. 2 starter behind Sabathia gave Burnett a comfortable feeling -- a lot like he enjoyed in Toronto, when Roy Halladay shouldered the load and let Burnett slip by.
After 244 career starts without one in the postseason, Burnett finally got his taste with the Yankees, following a season that saw him go 13-9 with a 4.04 ERA in 33 starts after signing a five-year, $82.5 million deal.
He was also the clubhouse prankster, giving birth to the tradition of delivering whipped cream pies to the player responsible for walk-off victories -- in the Yankees' case, an event that happened 15 times during the regular season.
After the Yankees' Game 6 victory, Burnett followed through on a season-long promise to get Girardi with the ultimate pie.
"I got him when it counts," Burnett said. "Any time you think it couldn't get any better, this place gets better. This is the best place to play."
The Yankees had prioritized pitching, but Teixeira was the biggest wild card -- the item on the shopping list that no one had written in, but the impulse purchase near the checkout line.
Cashman's trade with the White Sox in November for Nick Swisher had given the Yankees a decent option at first base, and as they would find out with his season, there was a lot to like offensively about Swisher.
But Teixeira was a premier offensive player, an impact switch-hitter and a Gold Glove-caliber defender who could change the Yankees' lineup for years to come -- and he appeared on the verge of going to the Red Sox, where he would torment New York for years to come.
Though he said earlier in the day that the Yankees weren't interested, Hal Steinbrenner reversed course and authorized what would be an eight-year, $180 million commitment to Teixeira in December.
Christmas came early for the Yankees and for Teixeira, who hit .292 with an American League-leading 39 homers and 122 RBIs while contributing eye-popping defense before celebrating the first World Series title.
"This is why I came here," Teixeira said. "All the hard work, all the ups and downs, this is why I came. ... Every season, you put up good numbers, and if you're not a champion, you feel bad. This is the first year in my career I can go home after the season is over and be completely happy and completely satisfied."
As Cashman walked through the concrete tunnels of Yankee Stadium in the early morning hours on Thursday, his slim grin was one of fulfillment. He wore a backward New York Giants cap and cradled his young son, Teddy, already barefoot and asleep in his arms.
"Some years, it works out. Most years, it doesn't; but some years, it does," Cashman said. "Thankfully this is a year that we were able to do something for the city and the Boss. The whole year was a remarkable year."
The biggest gambles had paid off, and for that, Cashman would rest well -- for a night. The work will begin again all too soon.
Bryan Hoch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.