Jay didn't even make the junior varsity team as a freshman. He joined the varsity his sophomore year but didn't start until his junior season. Such was the reality for players trying to break into one of the Miami area's elite high school programs—Columbus High School.
As a senior, Jay was a member of a state championship team
He expected to wait at the University of Miami too, signing a letter of intent at a school that, at the time, had four junior outfielders. Jay didn't care. It's where he wanted to play. Circumstances—two transfers and an injury—created an immediate opening for him, even though Jay had already braced to wait.
He finished his collegiate career a three-time All-American.
In 2006, Jay was a second-team preseason All-American after holding down the leadoff spot for Team USA in the summer of 2005.
During the winter before 2007 spring training, Baseball America rated Jay as 5th-best prospect in the Cardinals' organization. And in the offseason before 2008 spring training, the magazine had Jon down at #10 in the St. Louis farm system.
In the spring of 2009, they had Jon at 12th-best in the Cardinal organization. And he was at #13 in the spring of 2010.
Jay has impressive instincts and a real feel for the game.
A lifelong Miami resident, Jay tried his hand at paddleboarding, a water sport in which a rider lies on a board and uses his or her arms to maneuver through waves. Jay bought two paddleboards, he said, and made regular visits to the Atlantic Ocean to experiment with them.
But what began merely as a form of active entertainment became a workout tool for the Cardinals outfielder.
"It's a great core workout, so it allowed me to work out and have a good time at the same time," Jay said. "Even before I left to come to camp, instead of being so much in the weight room, I tried to do more paddleboarding. It worked out well. I knew I would be in the weight room a lot when I got here, and so that broke the workouts up and still provided good core work."
A Miami native, Jay won a state championship at Christopher Columbus High School and was a standout at the University of Miami.
Then, in 2006, he was drafted in the second round by the Cardinals.
"Every father dreams of seeing their kids succeed," Jon's father, Justo, said. "He's living his dream, but not just because he is playing baseball. He's being successful on the ball field, but he is successful as a human being and he was successful as a student. We definitely feel blessed, because we know how difficult it is to make it to the big leagues. It's one in a million to get there, and we don't take it for granted that he has made it here."
Justo, who was wearing his son's Miami Hurricanes jersey to the Cards/Marlins game on Father's Day in June 2013, said he felt "true joy" when he saw Jon trot out to center field. His son then hit an RBI single in the third inning.
"We're blessed to be in this position to be here supporting him," Justo said. "Joy shared is twice the joy, so when he comes to Miami, we get to share this with all of our family and friends and the joy gets multiplied."
"It's surreal to know that I am able to wear a big league uniform," Jon said. "I love to come home to Miami and play in front of people that I grew up with in the city that raised me. It's an incredible feeling." (6/16/13)
At various times, he has been nicknamed "The Federalist," "The Founding Father," and "The Chief Justice" in honor of the U.S. Founding Father John Jay and his contributions to The Federalist Papers.
Spring 2015: Jay returned to game action after offseason surgery, making his first grapefruit appearance.
While getting ready for the 2015 season, Jay has spent a lot of his time coaching the team's young outfielders.
"I told my wife the other day that I felt like I've been a coach for three weeks," he said. "I'm getting there early and getting all my stuff done by 11 o'clock. Then it was almost like I became a coach after that. It's something I enjoy doing. It keeps my mind fresh. All the younger guys want to get better and it's kind of cool. [I'm] just trying to do my part." (Paul Hogan - MLB.com - March 20, 2015)
2015 Spring Training: Inspired by a drill that he saw at a University of Miami football practice, Jay prepared for the new season with the assistance of a tennis-ball machine. He wasn't the only Cardinals player to employ the unique resource.
Jay introduced the ball machine to his teammates in the spring of 2015, bringing it with him to camp and demonstrating how it could help improve first-step quickness. The outfielders set up the machine to feed tennis balls for about 15 minutes and then went about catching them glove-free.
"You have to watch the tennis ball all the way into your hand, have soft hands," Jay explained. "You have to really concentrate. You don't really know when the ball is going to come out, so that forces you to have a quick first step. I relate it to, in the outfield, as soon as a ball is hit, I have to make a good judgment."
While the exercise broke up some of the monotony of early spring drills, it was particularly useful to Jay after the 2015 season. He followed a routine in which he would have the machine feed him tennis balls as grounders, then line drives, and last as long fly balls. It also became an exercise in conditioning, as Jay would go at it non-stop until the bucket of tennis balls had emptied. (Jenifer Langosch - MLB.com - 3/25/16).
November 29, 2016: The same day Jon signed with the Cubs, his wife gave birth to twins.The Cubs and Jay began talking about a deal at the GM meetings days after the World Series as the team stressed the need for the right fit in the clubhouse.
"One of the things that I respected is that the Cubs made it clear they are careful about the players they go after and recruit," Jay's agent, Nez Balelo, told ESPN. "The Cubs have built a chemistry over the past two seasons they believe has helped them evolve into a winner.I believe Jon Jay checked all of their boxes."
The signing could mark the end of Dexter Fowler's career in Chicago. The free-agent outfielder is expected to receive a multiyear deal elsewhere. (Jesse Rogers - ESPN - 11/30/2016)
November 29, 2016: Jay's wife delivered twin girls. That was the same day Jon signed with the Cubs for a year. "I got done with my workout, and my wife and I were lookig to get a new car because I was going to get rid of my little sports car to get a dadmobile," Jon said. "We had just finished there, and the doctor called saying we had to come to the hospital. Then, she started having contractions So we were on our way to the hospital actually when the deal got announced, and she starting going into labof that night!"
With the Cubs down 11-2 to the Brewers, Joe Maddon didn't feel the need to use any more of his relievers. Instead, he brought in a secret weapon. A player who puts batters away with 60-mph curveballs and 56-mph slow-pitch softball changeups. An outfielder who's never pitched in his pro baseball life. A man named Jon Jay.
The lefty gave up one single and no runs on pitches that all registered under 67 mph. His final out of the day came during an eight-pitch battle with Yadiel Rivera, in which Jay unleashed some 47-mph cheese and finally retired the infielder on a 59-mph "curveball."
He told MLB.com's Carrie Muskat postgame, "I might have broke a record for slowest pitches." (Monagan & Muskat - mlb.com - 7/6/17)
When Jon signed his one-year contract with the Cubs in November 2016, no one knew the veteran would be the one to fill David Ross' role on the team. If you're looking for an X-factor on the Cubs, someone under the radar who has provided a major contribution, Jay is the man.
"It's just the way he goes about his business every day in a professional manner, he creates a good example," Kyle Schwarber said. "He goes out and shags early. He has his own routine, what he does in the cage. Being in the outfield, there's constant communication. As a younger player, it only helps and gets you better. You pick up things from a guy like him who's been around and been to a couple World Series already. He's been a clubhouse leader, a leader on the field. You can't say enough about what he's done for this team."
Jay is different. He is devoted to Miami -- his nickname for Players Weekend included the city's "305" area code. Every day, he wears an orange and green Hurricanes knit cap -- manager Joe Maddon likes to call it a "beanie" -- plus his orange Crocs. The plan in Spring Training 2017 was to have Jay, 32, help mentor Albert Almora Jr. in center field, with the two sharing the spot. Schwarber was projected as the leadoff man, so Jay spent most of the first half at the bottom of the order. But Jay worked his way to the top.
"I really attribute that to Jon Jay's work ethic," Maddon said. "This is the kind of guy who loves this stuff and he wants to be there. Jon Jay knows there's other guys who can play his position -- [his attitude is] 'nobody's going to take my spot.' He's playing from that mindset. Give him all the credit in the world. He's forced us to that setup."Jay fit in perfectly with the group.
"He always talks," Jason Heyward said. "He's very in-tune to what's going on, good, bad or indifferent. How can we do something better the next time? His mind is always working. He's preparing for the day, before and after the game. It's a treat to get to work with someone like that." Wasn't Ross like that last year with the Cubs? "Absolutely. We just got it in a different form of an outfielder, who's running the bases, who's playing. It's huge to be versatile in that role. He stepped right in and he's been what we needed," Heyward said.
Jay impressed his teammates again with a 15-pitch at-bat against the Brewers in which he fell behind 0-2, then took two pitches, then fouled off 10 in a row before hitting a single. His goal? To get on base. "It's something I take a lot of pride in," Jay said of his at-bats. "I'm just trying to stay consistent out there and stay in my lane and do what I can."
"That guy has a knack for a professional at-bat every time he's up there," Schwarber said of Jay. "To see him go up there and grind, it's all good stuff."
"He does not cave in; he's able to move the ball," Maddon said of Jay. "That's the throwback component of him that I really appreciate, which is how he works at-bats."
Jay has played in two World Series with the Cardinals. He knows what it takes both on and off the field. "When you're a good person, good guy, it goes a long way in the clubhouse," Kris Bryant said. "I can't say enough about him."
"He's a baseball player," Heyward said, which may be the ultimate compliment. "He's always looking at ways to try to beat the other team and always looking at ways to pass it along. He's just aware and pays attention to detail. He finds a way to get something done that's going to help us win." (Muskat - mlb.com - 10/1/17)
Jan 8, 2019: When the White Sox signed free agent outfielder Jon Jay, it marked an important move far beyond its effect on the depth chart. You see, with relief pitchers Ryan Burr and Ian Hamilton already on the roster, Jay's signing now gives the White Sox three Founding Fathers. That has to count for something!
In case you don't remember your high school history classes, (Aaron) Burr was Thomas Jefferson's vice president, (Alexander) Hamilton was the first Secretary of the Treasury and John Jay was the first Chief Justice for the United States. Now all the White Sox need to do is hire Ron Washington as a coach and acquire Nick Franklin and Matt Adams and they'll have assembled something really special.
Of course, putting together the Founding Fathers wasn't the only reason fans, writers and conspiracy theorists were excited by Jay's signing: The outfielder often spends his offseason training with recent White Sox acquisition Yonder Alonso and, oh yeah, Manny Machado. (M Clair - MLB.com - Jan 8, 2019)
2019 Spring Training: When Jon Jay makes his Chicago White Sox debut this spring, he’ll be wearing a number that’s very familiar to longtime fans.
It was 25 years ago that NBA Hall of Famer and Chicago Bulls legend Michael Jordan sported the No. 45 as he attempted to transition from professional basketball to a potential Major League Baseball career with the White Sox. Now Jay, a 33-year-old journeyman outfielder, is bringing the number Jordan made famous back to White Sox camp, and he’s doing so as a tribute to “His Airness.”
“Every year, I always have different numbers bouncing around from different teams
“Every year, I always have different numbers bouncing around from different teams. I kind of pay tribute to someone in my family,” Jay told NBC Sports Chicago. “I’ve worn numbers for people who have passed away in my life before. This year coming to the South Side I said, ‘Let’s see if someone is wearing 45,’ and it was available so it’s cool.”
Most sports fans associate Jordan with the No. 23. That’s the number he wore for the majority of his basketball career, including at the University of North Carolina. After Jordan abruptly retired from the NBA following the Bulls third straight championship in 1993, he announced plans to try living out his baseball dreams. As part of his career change, Jordan switched to No. 45. (Mark Townsend - Yahoo Sports - Feb.19, 2019)
June 2006: The Cardinals gave Jon a bonus of $480,000 after they chose him in the second round of the draft, out of the University of Miami. Steve Turco is the scout who signed him.
February 9, 2015: Jay and the Cards avoided salary arbitration, agreeing to a two-year, $10.975 million contract with the team.
Jon received a$1.25 million signing bonus and annual salaries of $3.5 million in 2015 and $6.225 million in 2016. He had asked for $5 million when the sides exchanged proposed one-year salaries last month and been offered $4.1 million. He is eligible for free agency after the 2016 season.
December 8, 2015: The Padres traded Jedd Gyorko and cash to St. Louis Cardinals for Jay.
Nov 3, 2016: Jay chose free agency.
Nov 29, 2016: The Cubs signed free agent Jay. Jon got a one-year $8 million contract.
Nov 2, 2017: Jay chose free agency.
March 6, 2018: The Royals signed free agent Jay.
June 6, 2018: Kansas City Royals traded LF Jon Jay to Arizona Diamondbacks for Elvis Luciano and Gabe Speier.
Oct 29, 2018: Jay chose free agency.