Maddon’s vision transformed for good cause

August 7, 2018

By Carrie Muskat |

Fruits of collaboration with artist to be auctioned for charity

KANSAS CITY — Jason Skeldon admits he wasn’t very good at playing baseball as a kid, but the Tampa, Fla., artist has made a big league connection as an adult. Skeldon and Joe Maddon have combined to create unique paintings to present the Cubs manager’s message about the game.

Maddon saw one of Skeldon’s paintings in a clothing store, and the two met.

“I’m not a huge baseball fan, but I did know Joe Maddon when he was with the Rays,” Skeldon said.

What was supposed to be a 20-minute meeting lasted two hours.

“The thing about it that was cool was we clicked,” Skeldon, 35, said in a phone interview. “I was very excited about the venture we’re in now.”

Maddon will write his ideas and send a PDF image to Skeldon via email. For example, Maddon wanted players to know they need to “build relationships” which leads to “trust” which leads to “exchanging ideas,” noting that the result is “constructive criticism flows.” Skeldon got all of that down in a Banksy-style painting.

In another piece, Skeldon created an image of Salvador Dali wearing a catcher’s mask, promoting the “tools of intelligence,” and has Mona Lisa wearing eye black and batting gloves and holding a bat. In Maddon’s writing, it says “Renaissance chicks dig the leather.”

“Joe, to me, besides being a baseball manager, Joe to me is artistic himself,” Skeldon said. “It has to do with baseball, but it has to do more than anything with an artistic vision that Joe has. It could be baseball, it could be football, it could be anything. Joe gives me ideas.

“It’s kind of funny — Joe does have to break it down for me a little bit,” Skeldon said. “I’ll say, ‘Who is this person?’ He’ll say, ‘He’s an All-Star, a Hall of Famer.’ I think at first, Joe kind of chuckled, but now he knows, so he’ll tell me right away. Things are very smooth.”

The paintings were Maddon’s way of “Putting the Art Back Into THEE Game,” as he says, and a different way to present his messages.

“He’s taking stuff coming out of my mind and making it real,” Maddon said of the collaboration with Skeldon. “He’s nailed it. All the stuff I’ve sent him and my thoughts to him, I think he’s put out there pretty clearly. Beyond that, his own personal touches, the colors, the way he layers things to me is right on.”

Fans will have a chance to purchase the paintings and meet Maddon and Skeldon on Friday at the Chicago Sports Museum, 835 N. Michigan Ave., Chicago, from 7-8:30 p.m. CT. One hundred percent of the ticket and art sales will be donated to Maddon’s Respect 90 Foundation. Tickets are $70 each.

Skeldon used to draw his own comic books when he was young. A paramedic for eight years, he returned to painting because it helped him deal with anxiety and depression. Now, Skeldon is not only an artist but also a philanthropist. He most recently sponsored a wedding for a couple in Lakeland, Fla., and has donated thousands of dollars to various causes.

Skeldon and Maddon work well together.

“I like to use everything he gives me, and I think that’s why we have a good relationship,” Skeldon said of Maddon. “His vision might be a little scrambled in his head, but it’s cool ideas. I’ve done this for years — people want their dogs with a crown on their head, with a bow tie, sitting on a mountain. I know how to ‘collab’ everything and get it all together, so that’s my strong point and his point is the vision.”


Carrie Muskat has covered the Cubs since 1987, and for since 2001. You can follow her on Twitter @CarrieMuskat.