When the Phillies traded for J.T. Realmuto a few days before the start of spring training in 2019, general manager Matt Klentak addressed the possibility of a contract extension for the best catcher in baseball.

“I think it’s a good idea to date the person,” he said, “before you ask to marry them.”

It made sense not to rush. The Phillies controlled Realmuto’s rights for two seasons, ample time to get better acquainted before getting serious.

But 23 months to tie the knot? Few expected such a lengthy courtship — or that the whole thing would almost get called off, with Klentak losing his job in the process.

Ultimately, the Phillies and Realmuto needed each other too much to split up. That’s how, 719 days after the three-for-one trade that sent stud pitching prospect Sixto Sanchez to the Miami Marlins — and with none other than Bryce Harper leading the “#SignJT” chorus that echoed through the empty bleachers at Citizens Bank Park last summer — the sides wound up staying together for five years and $115.5 million, including a $10 million up-front deferral to lighten the Phillies’ load in 2021.

The deal, agreed upon Tuesday, gives Realmuto the highest average annual salary for a catcher at $23.1 million, eclipsing by $100,000 the extension signed by Joe Mauer 11 years ago. It smashes the biggest payouts for a free-agent catcher by AAV ($18.25 million for Yasmani Grandal in 2018) and overall value ($85 million for Brian McCann in 2013). And it’s the third $100-plus million contract for a catcher, joining Mauer ($184 million) and Buster Posey ($167 million extension in 2013).

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But it also resembles, in dollars and length, the nine-figure proposal made by the Phillies in March — before the pandemic ended spring training, cut the season to 60 games, closed ballparks to fans, and altered baseball’s short-term economics. It also falls within a contract structure that compares catchers to other catchers rather than to all position players, a system Realmuto and agent Jeff Berry endeavored to topple.

Two questions, then, spring to mind:

  • If negotiations between the Phillies and Realmuto ended almost where they began 10 months ago, why did it take so long to reach an agreement?

  • Why didn’t Realmuto’s market materialize as his camp expected?

Details from multiple sources over a period of months helped make sense of it all.

Taking a position

The Phillies’ first multiyear offer to Realmuto came early in the 2019 season — almost a year before most people were paying attention. Although the terms are not known, the offer is said to have aligned with the catching market, which included Grandal’s free-agent deal with Milwaukee a few months earlier.

But Realmuto, who turns 30 in March, is 28 months younger than Grandal and was aiming much higher.

Philadelphia fell hard for Realmuto in 2019. He batted .275 with 25 homers and an .820 OPS, led the majors in caught-stealing rate (47%), and was the first NL catcher since Yadier Molina in 2013 to win the Gold Glove and Silver Slugger awards in the same season. The Phillies planned to rekindle contract talks last winter, but preferred a deal that wouldn’t begin until 2021.

They offered Realmuto a 2020 salary of $10 million, an arbitration record for a catcher. Berry, formerly a minor-league catcher who brokered Posey’s extension with the San Francisco Giants, wanted $12.4 million, citing statistical comparisons that went beyond catchers and aligned with star third baseman Anthony Rendon.

“You shouldn’t get paid less to squat for a living,” Berry said last year. “It doesn’t take an Ivy League degree or a judgeship to figure that out.”

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Realmuto’s case went to an arbitration hearing in February, and a panel ruled in the Phillies’ favor. The next day, managing partner John Middleton waited for Realmuto to take batting practice and walked with him to an adjacent field. While both sides claimed no animosity, Berry said players “never forget an arbitration hearing.”

It also was evident that Berry, who has similarly crusaded to upend the system for closers (he represents Milwaukee’s Josh Hader), wouldn’t relent in trying to change the bar for catchers.

There are reasons why a catcher’s value is weighed on a different scale, according to former New York Mets general manager Steve Phillips, who negotiated a $91 million extension with Mike Piazza in 1998. Even elite catchers rarely play more than 140 games in a season, a fact that Phillips said comes up in arbitration cases.

Durability concerns increase with age. Forty-seven catchers have gotten at least 500 plate appearances while playing 75% of their games behind the plate in their age-30 season, per Baseball-Reference.com. The group whittles to 41 catchers at age 31, 29 at age 32, 18 at age 33, 19 at age 34, and 12 at age 35. Thus, no free-agent catcher has signed for more than five years.

Berry argued that Realmuto’s athleticism will enable him to buck the catcher aging curve. But Realmuto has also been injured in the last two Septembers, including a strained hip flexor last year.

The Phillies nevertheless understood that locking up Realmuto would probably mean making a record offer. They opened new talks in March with an offer of slightly more than $100 million; Realmuto’s camp countered in the $200 million range.

Once spring training stopped, Major League Baseball imposed a freeze on transactions. When it was lifted in July, the chasm between the sides hadn’t narrowed.

Like most teams, the Phillies were braced for a fall in revenues from the truncated, fan-free season. They held firm on their spring offer, with Klentak noting in July that “the landscape we left in March is different from the one we return to now.”

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Realmuto, meanwhile, pointed to Mookie Betts’ $365 million extension with the Los Angeles Dodgers as a sign that money would still flow for elite players.

“I still think teams at the top of the market are going to be willing to spend money,” Realmuto said last summer, while conceding that “half or even three-quarters of the league might not be as interested in spending as much.”

Harper, meanwhile, became Realmuto’s chief lobbyist. During batting practice, he wore a promotional giveaway T-shirt with the catcher’s name and No. 10. After Realmuto homered in an intrasquad game, Harper shouted, “Sign him!” Intrepid fans jumped aboard the campaign, with a “Sign J.T.” banner appearing near the players’ entrance to Citizens Bank Park.

If not for the pandemic, would the Phillies and Realmuto have found common ground?

It’s impossible to say. But they were so far apart, with such vastly different outlooks on his value, that an agreement seemed doubtful. Besides, having already received a $100 million-ish offer from the Phillies, what was the harm for Realmuto and Berry in seeing how much more they could get?

Going to market

It’s likely no consolation to Klentak, who stepped aside on Oct. 3 to avoid being fired after the Phillies missed the playoffs again, but he read Realmuto’s market perfectly.

As the offseason began, few teams signaled an appetite to increase payroll. Many, including the Phillies, had massive staff reductions. Even though Middleton and team president Andy MacPhail said signing Realmuto was a “priority,” team officials were pessimistic.

Then, the Mets bowed out of the bidding.

If Berry could compel any team to negotiate outside of a catcher’s contract constraints, it figured to be the Mets under the new ownership of hedge-fund billionaire Steve Cohen. Instead, they signed James McCann, the second-best free-agent catcher, for four years and $40 million.

Some Phillies officials were shocked that the Mets didn’t choose Realmuto. Other potential suitors disappeared, too. The New York Yankees, Washington Nationals, Los Angeles Angels, Toronto Blue Jays, and Houston Astros had other priorities or found less expensive catching solutions.

The week the Mets signed McCann, the Phillies hired two-time World Series-winning executive Dave Dombrowski to lead baseball operations. Berry called Dombrowski on Dec. 21. Two days later, on a planned trip to visit his wife’s family in Oklahoma, Dombrowski met Realmuto for lunch near his home there.

Negotiations began shortly thereafter. With the March offer serving almost as a baseline, the Phillies made a five-year bid worth $107.5 million, according to USA Today.

Dombrowski claimed the Phillies had “Plan B’s and Plan C’s,” but seemed to not even wince as other free-agent catchers (Mike Zunino, Curt Casali, Kurt Suzuki, Jason Castro) came off the board.

The rival Atlanta Braves were reportedly “circling” on Realmuto last week. They almost certainly couldn’t match the overall value of the Phillies’ offer, but might have proposed a shorter term and higher average annual value. As a catcher, and given the chaos of COVID-19 and a potential work stoppage after this season, it would’ve been difficult for Realmuto to accept one or two years.

The Phillies finally inched above Mauer’s $23 million AAV, and Realmuto agreed to defer $10 million of his 2021 salary until 2026 and 2027, when revenues figure to be back to normal.

Did the Phillies bid against themselves? Maybe. While they claim to have not felt pressure to appease Harper, Middleton is acutely aware of public opinion. The outcry over letting Realmuto walk would’ve been loud from outside and inside the clubhouse. But the Phillies also weren’t going to retreat from their March offer to a player they wanted to keep.

Putting a ring on Realmuto’s finger, at long last, won’t clinch a World Series ring. The Phillies have missed the playoffs nine years running (including the last two with Realmuto), the NL’s longest active October drought.

But their odds of contending are better with Realmuto. It turned out he needed them just as much.