October 2, 2022

‘I’ve never had more fun’

Read Time:8 Minute, 31 Second

Jackson Olson feels like he is living in a dream.

It is not the dream he envisioned, getting drafted by a Major League Baseball team out of college. The path he has taken to get where he is was certainly not planned, but Olson said he would not change any of it.

Olson has over half a million followers on TikTok, another 120,000 on Instagram, just completed a tour of MLB stadiums where he did everything from throw out first pitches to trying every food item stadiums had to offer and Friday night will be making his debut for the Savannah Bananas in a game broadcast nationally on ESPN2.

Not bad for a guy who was delivering groceries for Instacart a little over a year ago.

“I didn’t have a plan, but I knew I wanted to try to do something different. At first, I was just having fun. I never thought it would get to this,” said Olson, a 2016 graduate of New Milford High School. “I basically started on this journey a year ago and everything that has happened since then is beyond anything I could have imagined. My parents didn’t understand at first but they had faith that I would make something out of this, but none of us imagined it getting to where it is now.”

Where Olson is now is on the cusp of playing his first game for the Bananas, where he can marry his love of playing baseball with his passion for creating social media content geared toward younger baseball players and fans.

Olson was originally on the path of many highly regarded young baseball players.

After a strong junior year playing at the University of Hartford, Olson played a season in the Cape Cod League for the Hyannis Harbor Hawks.

His success there led to the Arizona Diamondbacks offering him a contract.

@jacksonolson_ Replying to @patrickjudge Will part 3 happen this year…? #mlb #foodie ♬ GREEDY x TREASURE – conradrocha

Olson turned it down, hoping to return for his senior season and taking his chances in the MLB Draft.

Then the COVID-19 pandemic took over, the draft was reduced to five rounds and many players like Olson were left in the lurch.

“COVID hit and everything went bonkers,” Olson said. “I transferred to Stetson where I played my final year of college baseball. As I was doing that, I was also posting more on social media and realizing I loved that, too.”

He was not drafted after a year at Stetson and thought his baseball career may be over, but embraced his new love of creating content in the form of videos dubbed with movie quotes, skits in the locker room and more.

@jacksonolson_ Trust yourself and trust your journey, it’s always up to you #mystory #baseball ♬ Dandelions (slowed + reverb) – Ruth B.

His videos gained more and more attention and soon millions of people were viewing them across multiple platforms.

After he played his last game at Stetson, he needed a job and took a gig working for Instacart delivering groceries. He continued making videos about his new job, which continued to attract more people to his feeds.

Someone working for Major League Baseball saw his videos and reached out to Olson about becoming a member of MLB’s first ever Creator Class in 2021.

Olson was hired along with 10 others to create unique baseball-related content on TikTok in an effort to reach a younger audience.

As brand ambassadors for MLB, the Creator Class posted videos which got more than 45 million views in a few short months.

@jacksonolson_ 3 months of nonstop fun… and my favorite job so far #mlb #baseball original sound – Roblox acc

Olson was able to attend MLB games and allowed fans to get an up close look on and off the field.

The Creators were asked to make 12 videos, but Olson went above and beyond, posting 75 videos and blowing away the rest of the team.

“I knew I had to take advantage,” Olson said. “It is just like working at baseball. If you want to get better, you go to the cage and take 1,000 swings. Doing social media is no different, It’s all a grind and the more you put into it, the better the results. You put everything you have into this game but what I have realized this past year is that you have to have fun too.”

Olson credits Hartford baseball coach Justin Blood with lighting a fire under him which continues to fuel him to this day.

“Nobody was ever harder on me than Justin Blood,” Olson said. “He saw something in me and wanted to push me. He taught me that every rep counts. He wanted to make me better. Extra reps is the same thing as extra TikToks. It is all the same mentality, that if I out-work everyone I will succeed. There is always someone who wants to take your spot, don’t let them.”

That led to Olson getting hired by a ticket company called Gametime, which offered to send him across the country to rank MLB stadiums and post videos.

On that trip, Olson tried nearly every food item offered at various stadiums, though he had to slow himself down after noticing he was packing on pounds.

“I was eating everything at first and I went from 185 to 195 in two weeks,” Olson said. “Once I got to the east coast stadiums I would usually just take one bite then give the rest away. Though some of the stuff was so good, I had to finish it.”

He was doing much more than just eating. Olson was able to experience ballparks in a way few do.

He threw out the first pitch at several games, was featured on the jumbo-trons to pump up fans, shagged balls during pregame in the outfield of a few stadiums and even got to slide on Bernie the Brewer’s slide at American Family Field, home of the Milwaukee Brewers.

Olson said getting to go on the slide was definitely a highlight of his trip.

However, something else happened in Milwaukee that would make an even bigger impact on Olson.

“After I threw out the first pitch at the Brewers’ game a few young fans were waiting to get my autograph as I came off the field, which was nice,” Olson said. “Then when I got up the concourse, I saw a huge line of people and thought maybe an old Brewer was signing autographs. The security guard had his arms folded and was staring at me and told me all these kids were in line to see me. As I was signing autographs and taking pictures a guy who was like 45 said to me ‘who the (expletive) are you?’ and a kid on the line said to him ‘he makes baseball fun.’ I nearly cried realizing I am influencing young kids in baseball like that.”

@jacksonolson_ The question is… will I see the last 10 stadiums this year? #mlb #baseball Sunroof – Nicky Youre & dazy

For the record, Olson rated San Francisco’s Oracle Park as his favorite stadium.

Through creating content, Olson had found his passion for the game again.

“I love this game. It can get away from you and you can lose your love for it, but what I realized meeting people in all these ballparks was that baseball is supposed to be fun,” Olson said. “You never know when it will end and you have to get all the fun you can out of the game. I have been told by more than one 12 year old ‘you made me love baseball again.’ Baseball is just so romantic.”

With his love of the game reignited, Olson then got a call he was not expecting from the Savannah Bananas.

For those who do not know, The Bananas play a different brand of baseball geared toward entertaining fans with players dancing in games, people taking at bats while on stilts or with flaming bats and rules for a fast-paced style developed to draw in more fans, especially younger ones.

Recently, ESPN announced it would air a documentary series called “Bananaland” following the minor-league baseball spectacle, which plays in the Coastal Plain League.

The series is set to premier Friday, August 19 and though Olson was not with the team when the series was filmed last year, he will be a part of season 2.

But Olson will be playing for the Bananas on ESPN2 which will be airing his first game at 7 p.m. ahead of the premier of the show.

ESPN2 and ESPN+ will also air live games August 20th, 26th, 27th and September 2nd and 3rd.

“I can’t believe I will be playing for the Bananas on a national broadcast,” Olson said. “I kept getting bigger posting on social media and loved it. Now, the Bananas will let me post TikToks during games. It is all coming together. Being able to play baseball but also keep doing the social media. The owner (Jesse Cole) is such a great visionary and it is so cool what they are doing there. I am so excited to be a part of it.”

The Bananas are also going to incorporate Olson’s food reviews into the game.

Olson will play third base and at times a table will be set up near third base with different foods from the stadium for Olson to try. So there is a chance Olson could be on ESPN2 eating food at third base, which he still can’t fully wrap his head around.

Olson said the game is played at a faster pace than anything he has ever experienced and he is also learning things he never thought would be part of baseball practice.

“It’s so fast, if you look down at your cleats, the next pitch has already been thrown,” Olson said. “This week I have been working a lot on the ‘Greatest Showman’ dance which I will do in costume before an at bat. I’ve never had more fun playing baseball.”

Sericson@stamfordadvocate.com; @EricsonSports



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