If you know the drill, then it was easy to comprehend. Jimmy Garoppolo was the San Francisco 49ers quarterback. Then it was quite widely known, at the end of the 2021 season, that he would no longer be of service and a trade would be on the horizon. And then, Jimmy Garoppolo was the quarterback again. And again. It's sports at its finest; what you expect often doesn't happen, and there are beautiful surprises along the way. 

Rita Oak started off with a simple task; thanking Jimmy for his time as the Niners QB and drew an ode to him on her IG. And then, until he was traded, she was just going to continue to draw him. And draw things about him. And draw things involving him and some things that didn't involve him. For 404 days, she drew him, gaining an international audience from her home in Portugal and caught the eye of ESPN, the Athletic and other major sports media. And us. 

As her project came to a, well, sort of end when Jimmy was let go and now has officially headed off the the Las Vegas Raiders, we sat down with Rita to talk about the project itself, the growth from it, what she learned and what's next. 

Day 11
(Day 11)

Evan Pricco
: How long did you actually think this project was going to last? 

Rita Oak: When I first started I really thought this would last 1 or 2 months max and I honestly didn't think it would last as long as it did. Jimmy was supposed to get traded by the end of March, he even held a press conference saying goodbye to the team. So we were really taken by surprise once we heard he was staying with the team for another year. I guess that was the only outcome we didn't predict. At that point we had to make a decision on whether to stop here or to continue with the series, but after weighing the pros and cons we decided to continue. I felt like I would keep on going while it still made sense for me and honestly I'm glad that I did. 

Did you always have that last piece in mind? 
The idea for the final drawing never changed, I think it was a suggestion actually, and we thought that the scene from the shawshank redemption would fit perfectly with what we had in mind. So when we got the news of Jimmy staying we just saved the idea. 

We didn't want it to be just a drawing, we wanted to make it special and add some emotion to it. So we came up with the idea of adding the quotes from the players, Kyle Shanahan and John Lynch. I just wanted people to see how great of a person and player Jimmy really is and find a way to see him through the other players' eyes. 

Any artist who spends so much time on a subject obviously grows with the subject, so how did you grow with both Jimmy and of course, the NFL?
I guess looking back I can say that I grew as an artist and I learn a lot about American Football (keeping in mind that I didn't know anything about this sport). My boyfriend, Filipe, really helped me understand it better and taught me all the rules as we were watching the games. As well as introducing me to all the teams and telling me about the players. 

Through this process I guess you can say that I connected with Jimmy in a way.. I obviously don't know him but I was always keeping up with everything that was going on with him and just drawing his face every single day, I think I created a connection. I will always be a niner fan and support the niners, but, at the same time, I will keep following Jimmy and watch him play wherever he goes. I hope he gets the opportunities he deserves and I am very excited he gets to be a QB1 again. I hope he gets a chance to prove himself and show his talent as a player. 

Day 170
(Day 170)

How do you feel you changed as an artist through this process? 
I feel like this was a great way to find myself in my art and figure out what I wanna do with it. I really love drawing the niners and sports in general, so I will keep on doing that in the future. I also got to learn a little bit more about Procreate (the app where I make my drawings) and I think if we go back to the beginning and compare the drawings we can definitely see some growth. At the beginning I just wanted to make some quick doodles since it was going to be a drawing every day, but as time went by I started to add more details and took a little more time to draw them. I also started to add more players and create backgrounds, and I think that really made a difference! I think that gave more life to the series. 

When I first got my ipad, I got it because I really wanted to try digital illustration and I was a little lost. I didn't know exactly what I wanted to make, so before this series I was making drawings for my friends and family and selling some of them. Wasn't until I started drawing Jimmy that it really clicked for me and I found that sports illustrations are really a passion of mine! Just being able to put together two things that I love: Drawing (art) and Football! 

Did you expect to get so much attention for this project? 
Not at all. I started this whole series for fun and I never thought it would blow up the way it did. I was just happy to post some art on social media that would make people smile and bring a little joy to their days. I am very grateful for the community we were able to create with this series and the niners fans that took me in when I first posted on reddit are truly amazing! People showed me nothing but love throughout this process and It's because of them that I got this far. I am very grateful for all the opportunities that I got mostly for being able to make the trip to San Francisco. It was really a dream come true! I loved exploring the city and seeing the niners live for the first time! 

What did Jimmy think of all of it? 
When I got the video of Jimmy talking about me and my drawings it really took me by surprise! A reporter that had interviewed me, was interviewing Jimmy and asked about my drawings. He then emailed me the clip and I was at the supermarket at the time with my mom, and I just freaked out! I couldn't believe he knew about my drawings and liked them! Just getting his approval was everything! 

Throughout the series he sometimes watched my stories on instagram and liked one or two of my posts, so that was awesome! I don't know how he feels about them now but I hope he likes them and I hope he knows I did this out of love and respect for him. 

Final Jimmy BIG
(Day 404)

So what's next?
Obviously I am sad the series came to an end, and I even got a bit emotional after I posted the last drawing. It took me a few minutes to really sink in that it was the last one. But at the same time I am very excited for the future and for new projects! We already have some ideas that we like to explore! I will definitely keep drawing the niners and that will be my main focus, but I also would like to draw other teams and other sports as well, and try to reach other people with my art.  

Right now I am working on putting together a coffee table book of all the drawings in the Jimmy G series! I know a lot of people have been asking about it and that's definitely my next step!  

You can follow Rita's art at @Ritaoak_art