- June 12, 2025
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Ian Desmond spent most of his life dreaming about becoming a major leaguer and ended up living out that dream.
Desmond, a graduate of Sarasota High School, was drafted in the third round of the 2004 MLB Draft by the Montreal Expos and went on to have an 11-year career with the Washington Nationals, Texas Rangers and Colorado Rockies.
After five years of retirement, Desmond is back in the game, hired to coach the Lakewood Ranch High School baseball team on May 21, replacing four-year coach Colton Chupp.
For Desmond, returning to baseball is a story that’s come full circle, even if it looks a little different than he once envisioned.
Desmond officially retired from baseball in 2022, but he played his last professional baseball game for the Rockies in 2019.
He decided not to play the 2020 season during the COVID-19 pandemic and racial tensions at the time. He instead devoted time to his wife and five children and the Sarasota community.
His time away from the game led to him opting out of the 2021 season as well before finally calling it quits in 2022.
In total, he left $13.5 million in guaranteed salary behind — and the chance at a $15 million team option in 2022 — for a new phase of life.
That started with Newtown Connection, a non-profit organization Desmond helped establish that focuses on athletics and health for diverse and at-risk youth in Sarasota.
Giving back is nothing new for Desmond, who was nominated for the Roberto Clemente Award by the Rockies each year from 2017-21 for his philanthropy with the Children’s Tumor Foundation and Newtown Connection.
However, he said he always pictured himself becoming a high school baseball coach one day because of his coach at Sarasota High.
“I was really fortunate to play for Clyde Metcalf at Sarasota High,” Desmond said. “I called Clyde (May 21) and let him know that he made a lasting impression on me. For me, as a retired major league baseball player who could do anything, to go back and coach high school baseball is a testament to how he did it and how he showed me how to do it.”
Though Desmond said he always imagined he would be coaching the Sailors, life threw him a curveball.
Desmond has devoted much of his post-MLB life to philanthropy and the Sarasota community, but he’s also dedicated to his family.
Desmond and his wife, Chelsey Desmond, a former softball player at Riverview High, have five children together — sons Grayson, Cruz and Ashton and daughters Dakota and Naomi.
Grayson, the oldest, is set to become a freshman at Lakewood Ranch High this fall, with 12-year-old Cruz and 10-year-old Ashton not too far behind.
Being close to his children, and hearing of rumors of the coaching position becoming available, made Lakewood Ranch an appealing option, he said.
“I was joking with (Athletics Director) Kent (Ringquist) that I plan to be here to kind of eavesdrop on what they’ve got going on in high school, so I’d love to be here for a long time,” Desmond said.
Desmond said he plans to announce a summer workout program soon, and hopes to have the players working out in the fall as well.
Those extra practice sessions could prove vital.
Lakewood Ranch went 48-56-1 in four years under Chupp, including a 2023 season in which the team went 19-8 and reached the Class 7A regional semifinal round.
However, the Mustangs finished this spring with a 6-18 record. Rinquist would not comment on whether Chupp resigned or was let go from his position.
"He has a lot of ties to this area," Ringquist said of Desmond. "He's definitely connected with the youth programs, and his background playing at the highest level that you could possibly play and have success. He has a lot of great attributes that he can bring to our program that we're excited about."
There is reason to think that Lakewood Ranch could have a better season next spring.
Eight seniors graduated from the Mustangs's roster, but 14 sophomores or juniors could return for the 2026 season, including top-hitter Carter Sprague (.400 batting average over 20 games) and pitcher Chase Skarbek (2.66 ERA in 26 1/3 innings).
Desmond and the Mustangs will have some stiff competition in the area. Braden River is fresh off a season in which it finished 19-12 and made it to the 5A regional final round. Sarasota, Cardinal Mooney, Out-of-Door Academy and Venice each had winning seasons as well and also made it to the regional playoffs.
However, Desmond is no stranger to baseball in Sarasota and Manatee counties and is up for the challenge.
“If I’m being fully transparent, when I was in my career, thinking about what I would do post-career, I always thought I would go back and coach Sarasota, but life changes,” Desmond said. “Being in the community we’re in has been great. We have a phenomenal community around us, and I couldn’t be more excited to start this next chapter of my life at Lakewood Ranch High.”
