This time, the stakes are even higher.
When salary figures were exchanged on Jan. 20, Howard asked for $18 million, the third-highest request since the process began in 1974, with the Phillies also offering the third-highest salary, at $14 million.
The date for the hearing hasn't been released, but it will be scheduled at some point from Feb. 2-22.
Howard and first-year general manager Ruben Amaro Jr. can still come to terms on a contract at any time before the scheduled hearing, but whether or not that will happen remains to be seen.
When reached by phone recently, Amaro did not want to comment on the club's negotiations with Howard, simply saying: "Obviously, we'd be happy to get all of our players signed. We're just going to see how it goes, and if we have to go [to arbitration], then that's what we'll do."
Win or lose, Howard will be the highest-paid player on the Phillies again.
In fact, his request is nearly double the record for a position player in his second year of arbitration, with the previous high being Derek Jeter -- who asked for $10.5 million in 2000 before settling with the Yankees for $10 million. Currently, only 11 other players in the Major Leagues have contracts with an average annual value of $18 million or more.
"It's difficult in Ryan's case because he's really in uncharted waters," Amaro told The Philadelphia Daily News last week. "He's had the kind of success that's kind of beyond anybody who's been in his position."
Amaro wasn't kidding.
Howard's request comes after a season in which he led the Major Leagues with 48 home runs and 146 RBIs, further adding to an impressive big league resume.
In his first full season, Howard won the National League Rookie of the Year Award. In his second, he was named NL MVP. And over the past three years, no player in baseball has hit more home runs (153) or driven in more runs (431).
If he wins his case, the 29-year-old would have the second-highest annual salary among Major League first basemen, trailing Mark Teixeira ($22.5 million) and overtaking perennial All-Star Albert Pujols ($14.285 million).
While both those players sport higher career batting averages than Howard's .279, their home run and RBI totals over the past three years don't come close. Teixeira has hit 96 home runs and driven in 336 runs, while Pujols has hit 118 homers with 356 RBIs.
Last year, when the Phillies proposed $7 million at the hearings, Pujols was the player who came to mind. In 2003, after Pujols' third year in the Majors, the right-handed-hitting slugger was coming off a season in which he hit .359 with 43 home runs and 124 RBIs. That offseason, he asked for $10.5 million, while the Cardinals countered with $7 million. Instead of going before an arbitrator, however, Pujols wound up signing a seven-year, $100 million deal and made that $7 million his first season of the contract.
This time around, the arbitration comparisons aren't really there.
But one player who may come close in terms of production and value is Tigers infielder Miguel Cabrera, who will make $15 million this season in what would've been his third arbitration year. Last season, Cabrera -- currently signed to an eight-year, $152 million contract -- hit .292 with 37 home runs and 127 RBIs.
In the end, it may come down to the panel deciding whether Howard is worth more or less than the 25-year-old Cabrera.
But while the anticipation about his potential financial gain keeps building, Howard has been working out at his club's Spring Training home in Clearwater, Fla., since Jan. 5. On Wednesday night, while appearing on Comcast SportsNet's "SportsNite" program, he was asked how he would feel about a long-term deal.
"That would be beautiful," said Howard, who has registered three-plus years of service time, making him ineligible for free agency until after the 2011 season. "That would be something we would want to see happen.
"Maybe we'll be able to get something worked out."
One way or another, Howard and the Phillies will.