Anthony Richardson Sr honored by Eastside with jersey retirement as NFL future looms

Anthony Richardson Sr honored by Eastside with jersey retirement as NFL future looms

Former Florida football standout quarterback Anthony Richardson Sr. finds himself at the crossroads of his NFL career.

But on May 14, Richardson returned to Citizens Field in Gainesville for a special honor which brought back memories of where it all began for him.

Eastside High retired Richardson's jersey No. 2 during halftime of its spring game on Thursday night. Before the ceremony, Richardson was more than generous with his time, posing for pictures and signing autographs for all who approached him.

Richardson said every trip back to Citizens Field brings back memories of scoring touchdowns, getting tackled, throwing touchdowns and even throwing interceptions.

"All of it, really," Richardson said. "It doesn't feel real that they just retired my jersey. But I'm so thankful and grateful, I appreciate it and I'm just trying to work and keep on putting on for the city."

Richardson led Eastside High to city and district titles during his sophomore and junior year and was recently voted as one of the Gainesville Sun's top 10 area football players of all time.

"When I played in GainesviIle, didn't necessarily think about trying to be the top 10 in anything," Richardson said. "I was just trying to put on for my team, put on for my city and trying to win games. God blessed me enough to give me the recognition that I did and I'm just thankful for it."

Former Gator football player Anthony Richardson watches the sidelines during the Eastside High School spring football game when he returned to Gainesville for a ceremony retiring his high school football jersey, at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 in the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

Former Gator football player Anthony Richardson watches the sidelines during the Eastside High School spring football game when he returned to Gainesville for a ceremony retiring his high school football jersey, at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 in the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football game at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 in the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football game at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 in the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football game at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 in the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football game at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 in the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

Former Gator football player Anthony Richardson (center) returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

Former Gator football player Anthony Richardson (far left) returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

Former Gator football player Anthony Richardson (far left) returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

Former Gator football player Anthony Richardson (second from the left) returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

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Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson watches the sidelines during the Eastside High School spring football game when he returned to Gainesville for a ceremony retiring his high school football jersey, at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 in the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

1 / 15

Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson watches the sidelines during the Eastside High School spring football game when he returned to Gainesville for a ceremony retiring his high school football jersey, at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 in the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

2 / 15

Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson watches the sidelines during the Eastside High School spring football game when he returned to Gainesville for a ceremony retiring his high school football jersey, at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 in the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

3 / 15

Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football game at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 in the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

4 / 15

Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football game at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 in the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

5 / 15

Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football game at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 in the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

6 / 15

Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football game at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 in the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

7 / 15

Anthony Richardson Sr honored by Eastside with jersey retirement as NFL future looms

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

8 / 15

Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson (center) returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

9 / 15

Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson (far left) returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

10 / 15

Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson (far left) returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

11 / 15

Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson (second from the left) returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

12 / 15

Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

13 / 15

Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

14 / 15

Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

15 / 15

Anthony Richardson gets jersey retired at Eastside. See the photos!

Former Gator football player Anthony Richardson returned to Gainesville for a ceremony retiring his Eastside High School football jersey, during the spring football gamer at Citizens Field in Gainesville Florida, Thursday, May 14, 2026. After playing for Eastside, Richardson went on to play for the Florida Gators, and then was drafted in 2023 the first round by the Indianapolis Colts. [Cyndi Chambers/ Gainesville Sun] 2026

How former Florida football standout is approaching fourth NFL season

The 6-foot-2, 244-pound Richardson is entering the final year of his four-year, $33.9 million contract with the Indianapolis Colts. Reports surfaced that Richardson requested a trade during the offseason, but there were no takers. Richardson reported for voluntary OTAs with the Colts earlier this month.

"The Colts are still giving me a chance to go out there and work, work hard and potentially get on the field," Richardson said. "Glad to be able to stay in the NFL and put the work in. Just showing up at OTAs, it was a blessing in disguise for me because I just wanted to work and they allowed me to do that so I'm thankful for that."

Richardson was viewed as a potential franchise quarterback when the Colts took him fourth overall in the first round of the 2023 NFL draft. In 17 games and 15 starts for the Colts, Richardson has thrown for 2,400 yards with 11 TDs to 13 interceptions.

Injuries limited Richardson to four games his rookie season. After losing the Colts' starting quarterback job to Daniel Jones in training camp in 2025, Richardson appeared in just two games before suffering an orbital bone fracture while using an exercise band, which sidelined him for the rest of the season.

"All the adversity I thank God for because it only makes me a better person, a better player," Richardson said. "It only pushes me forward to be a better version of myself. I love being in the NFL, I'm thankful to be in the NFL."

With Jones likely sidelined to start the 2026 season after suffering a torn Achilles last season, Richardson could reclaim his starting job with the Colts if he beats out Riley Leonard in training camp. Richardson is still working with Jacksonville-based quarterback coaches Denny Thomspon of Six Points and Will Hewlett to prepare for the 2026 season.

"If I don't put that work in to be a better player then I won't be in the NFL," Richardson said. "I just want to work hard and constantly think about my opportunity that I have now and try to take advantage of it."

Anthony Richardson reflects fondly on his days with the Florida Gators

Richardson said he hasn't met new Florida Gators coach Jon Sumrall yet but reflects fondly on his days as quarterback with UF. He went 6-6 as a starter for UF in 2022, passing for 2,549 yards and 17 TDs while rushing for 654 yards and 9 TDs.

"I think about it all the time, watch my old highlights all the time," Richardson said. "They are just so surreal, it was four of five years ago, it was just so crazy honestly. I love coming back to Gainesville and miss being a Gator."

As Richardson continued to pose for pictures with fans and the Eastside High cheerleaders, it brought back more memories of his roots and his desire to give back. He's returned to Gainesville during summers to put on youth football camps and donated to local charities.

"People don't really know about the east side of Gainesville," Richardson said. "That's really where the struggle is. I grew up on that side of town and I know what it's like to be one of those kids, just like these kids playing for Eastside ...

"So I just try to give back anything I can whether that's wisdom, new equipment for the team, new uniforms, just anything to be a light to the next generation so they can put on for Gainesville."

Kevin Brockway is The Gainesville Sun’s Florida beat writer. Contact him at kbrockway@gannett.com. Follow him on X @KevinBrockwayG1.

This article originally appeared on The Gainesville Sun: Former Florida football QB Anthony Richardson Sr. talks NFL future at jersey retirement