It wasn't that bad, but about as close as one can get.
One year removed from a bulging disc in his neck that caused him to miss almost the entire season, and a few months after surgery to repair what eventually became a herniation, Dipoto had broken the two vertebrae that sat above and below a metal plate that was basically helping his neck stay in place.
Doctors told him he could try to keep playing, but there was a good chance he'd never even walk again if he did.
So, after battling back from thyroid cancer in 1994 and surviving a blood clot that temporarily stopped his heart four years later, Dipoto -- at 31, with no pain in his right arm and entering what could've been his prime -- was basically forced to retire.
"I literally went from being 100 percent in the middle of what should've been the best years that you have as a player, and it just got pulled out from under me," said Dipoto, who finished an eight-year Major League career with a 4.05 ERA for three teams. "It just stopped. The good part of it is that there really was no gray area that you could say, 'Well, maybe I could, maybe I should.' I just knew it was done and you had to move on."
Yeah, but that's hindsight.
The present moment didn't offer up that much perspective. Only tears.
On a soggy Wednesday morning on March 8, 2001, in Tucson, Ariz., the Rockies shut down their Spring Training operations and gave Dipoto a retirement news conference fit for a Hall of Famer -- not due to of his on-field talent, but his off-field kindness.
Every member of the Rockies' organization showed up to hear Dipoto speak that day, from the 47 players still in camp, to all the coaches, the training staff, the front-office members and even the owner.
Dipoto began sobbing uncontrollably, and pretty soon, several others followed.
"That's the hardest thing for us players to go through," said Gant, who was wiping away tears even though he had met Dipoto just three weeks before, to The Denver Post that day. "I know God only picks strong people to help others. And I know that's going to be part of what he does the rest of his life. I would say God picked the right person."
At last, Dipoto was able to pause, collect himself, and allow some words to fill up the room.
"I'm going to go home," he said, "I'm going to get some real pants and I'm going to come to work."
Eleven years later -- after front-office stints with the Rockies, Red Sox and D-backs -- Dipoto now wears the pants of the Angels' general manager position and went from unknown to rock star with two marquee signings at the Winter Meetings.
In some ways, Dipoto is still recovering from what was a whirlwind 72-hour gathering in Dallas, where he bounced from suite to suite at the Hilton Anatole, hardly slept and at one point was holding intense, down-to-the-wire negotiations with the agents for Albert Pujols and C.J. Wilson simultaneously.
Everybody wanted one of them.
On Dec. 8, Dipoto, barely a month into his first general manager job, got them both.
"A lot of times, people in his situation would be waiting to see what they're going to do and taking some time," his former boss, D-backs general manager Kevin Towers, said. "He hit a grand slam right off the bat."
But Dipoto was making headway long before that.
It began in July 2010, when he took over as interim general manager in Arizona upon Josh Byrnes' dismissal, then eased the D-backs' payroll, restocked their barren farm system and put them on the path to an eventual playoff berth with the savvy trades of Edwin Jackson, Chris Snyder and Dan Haren (now the Angels' No. 2 starter).
It happened through two interviews with Angels owner Arte Moreno and president John Carpino, who met Dipoto over breakfast and dinner in Arizona and ultimately chose him over a wide-ranging list of candidates.
And it happened on a grease board at his Winter Meetings suite, where it took Dipoto only 20 minutes to impress even the saltiest of scouts.
"Some of the guys that had been around for a while came out of there just in awe saying, 'Man, that's unbelievable,' and, 'We're in such good hands,' said Tim Schmidt, who worked for Dipoto in Arizona and is now one of his special-assignment scouts. "I look at them and say, 'Oh geez, guys, he's just getting started. He's got a lot more than that.'"
He had plenty more in the January organizational meetings he set up at the club's Spring Training site in Tempe, Ariz. Scott Servais, one of Dipoto's new assistant general managers, was in charge of putting together the agenda and needed to fill three hours. He figured Dipoto would take up one of them, so Servais was looking for somebody to open and close the day-one session.
No need. Dipoto took up the entire time breaking down his philosophies for constructing a 25- and 40-man roster.
"There was not one person who left those meetings there for two days and couldn't feel the energy and the passion he has for doing the job and taking the time to kind of pull back the curtain," Servais said.
Dipoto's track to his current position stems from the training tables of the Rockies' Spring Training complex in 2000.
Dipoto spent a lot of time there that spring, and so did Byrnes, who at that point was the assistant general manager in Colorado and was taking care of an elbow injury caused by playing pickup basketball. The two passed the time talking baseball strategy and roster construction, and Byrnes came away so impressed he had Dipoto sit in on several of their scouting sessions leading up to the First-Year Player Draft.
Soon enough, Dipoto was spending his off-time poring through scouting videos, ranking amateur players and advising scouts about the nuances of pitching in pre-humidor Coors Field.
"I think people working in these jobs have a lot of knowledge and passion, but I think some people feel like they aren't curious about what they don't know," said Byrnes, who's now the Padres' general manager and has known Dipoto since they crossed paths with the Indians in 1994. "I think Jerry has always been curious, always wanting to add to his knowledge and add to his experiences, and as a result, in the 10 or so years since he's stopped playing, he's learned a lot and he's ready to do the job."
Rockies general manager Dan O'Dowd figured he was ready very early. So early that the following spring, as Dipoto was shaken up after learning his playing career was over, O'Dowd cheerfully walked by, slapped him on the back and said: "You know what you're going to do, buddy? You're going to go home, talk to your wife, and you're going to work in the front office with us and help us build a champion in a different way."
And so Dipoto did, working in every aspect of the Rockies' system, then serving as a scout for the Red Sox from 2003-04, returning to Colorado as director of player personnel in 2005 and following Byrnes to Arizona the following year.
It may not have been enough to secure the full-time gig over a more-experienced Towers, but thanks in large part to the three trades Dipoto made as an interim general manager in July 2010 -- which brought back starting pitchers Daniel Hudson and Joe Saunders, and freed up the money to sign relievers J.J. Putz and David Hernandez -- the D-backs went from last to first in the National League West in 2011.
Shortly after Arizona was bounced out of the playoffs by the Brewers, the Angels and Orioles interviewed Dipoto for their general manager vacancies. And on Oct. 29, acting fast because he was already the frontrunner in Baltimore, the Angels announced they had chosen Dipoto as the 11th general manager in franchise history and the successor to Tony Reagins.
Moreno liked Dipoto's people skills, conviction, energy, playing experience and balance.
"I just really felt like he fit with what we were trying to accomplish," Moreno said.
"I liked his resume a lot because he had played. I like that. And I really liked the fact that he had a lot of experience doing different things. ... It's also a proper mix of good statistical analysis and good scouting information. Those are the kind of things that we picked up right away from Jerry."
Those who know him best would point out several traits that set Dipoto apart.
First off, he's a grinder. He got his tireless work ethic from his father, Jerry Jr., who worked his way up from trash boy at Schroder Trust to vice president at Chase Manhattan Bank.
He's perpetually curious. Dipoto was grilling Byrnes on the Rockies' draft strategy before he was even finished as a ballplayer.
He's uncommonly nice. He'll often respond to fans' questions and outlandish trade requests with hand-written letters.
He's a baseball junkie. In his basement in Colorado was a Cooperstown-like display of his lifelong memorabilia collection -- anything from signed balls, to game-used bats, to letters he wrote players as a kid, to a Sharpie-signed wall Don Baylor suggested he'd utilize for all the players who walked in.
He tends to be long-winded. During his interview with the Angels, he handed Moreno and Carpino a 45-page binder with his baseball philosophies, calling it his "living document."
He believes, as he put it, "in the good in players." In Dipoto's mind, Major Leaguers all bring a unique value, and it's up to a baseball-operations staff to identify how that value can fit within the framework of a championship team. While conducting an organizational meeting in Arizona a few years ago, he listed two very similar four-year sample sizes for two mystery corner outfielders. One ended up being Hall of Famer Carl Yastrzemski, the other was Brian Giles. The message: Leave no stone unturned.
He believes in controlling counts. While sitting in the car after Opening Day 2001, former Rockies manager Buddy Bell was raving to Byrnes about the outing Mike Hampton had because he limited his walks. Dipoto then poked his head out of the back seat and told them the walk column usually correlates with the earned-run column. Pitchers never say that stuff.
And he believes in balance, with religion, family -- his longtime wife, 15-year-old son and two daughters, ages 17 and 19 -- and, of course, the game that has dominated his entire life.
"It's more than a game to me," Dipoto said. "It's the constant in life. I have my family, I have my wife, I have my faith and I have baseball. That's kind of the standard."