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CHESAPEAKE, VA (WTKR)- American Legion Post 280 out of Chesapeake accomplished what just one other team from the organization in Virginia had ever done- win the American Legion national championship.

That achievement not only comes with the title of champions, but also a trip to be recognized at the World Series in October. Major League Baseball honors certain champions and teams during Game 2 of the fall classic, which will feature the Toronto Blue Jays taking on the Los Angeles Dodgers.

After initially being told they would be unable to attend the World Series because their scheduled game would be out of the country in Toronto, American Legion and the Major League Baseball Commissioner's Office reached a solution that will allow the team to attend Game 4 in Los Angeles. An American Legion spokesperson tells News 3 that how the team will be recognized at the game is still being worked out, but players and coaches are now able to go.

American Legion's national headquarters informed the team it would not be able to attend the originally planned Game 2 due to the contest being played in Toronto and concerns regarding venturing outside the United States. According to an American Legion spokesperson, the decision by American Legion was made based on international travel logistics, such as concerns over passports and necessary documentation, especially with the possibility of minors traveling outside the country.

Every American Legion national championship team has had the opportunity to attend a World Series game since 1927 and the resolution means that tradition can continue.

To add to the confusion, an Instagram post made Wednesday by Play Ball, Major League Baseball's youth initiative, reading “Congratulations to the 2025 American Legion National Champions Chesapeake, Virginia Post 280. We are excited to celebrate your achievements at the World Series."

Coach Larry Bowles tells WTKR News 3 that he was informed Thursday afternoon that his team would now be able to travel to Game 4 next Tuesday in Los Angeles. He also noted that his entire roster is comprised of players 18 and over. Now, after spending yesterday speaking with disappointed players and parents, he can relay the good news that they are heading to the Fall Classic.

American Legion Post 280 won the Senior World Series in Shelby, North Carolina, on August 19.

CHESAPEAKE, Va. — The superintendent of Chesapeake Public Schools has announced he is retiring at the end of this school year.

Dr. Jared A. Cotton’s retirement will be effective July 1, 2026, according to a press release from Chesapeake Public Schools. He has served as superintendent since 2018.

“Serving Chesapeake Public Schools has been the honor of my career,” Cotton stated in a press release. “Together, we have achieved incredible milestones that have enriched the lives of our students, families, and community. I am deeply grateful for the support of our dedicated staff, school board, and partners who made our vision a reality.”

The Chesapeake School Board will announce plans for the selection of a successor in the coming weeks, they said.

“Dr. Cotton has led Chesapeake Public Schools with integrity, compassion, and a relentless focus on what matters most, our students,” said School Board Chair Angela Swygert. “His ability to unite people around a shared vision for excellence has made our school system stronger and more connected to the community we serve. We are sincerely thankful for his leadership during some of the most trying times in history. Dr. Cotton leaves behind an undeniable legacy of success and innovation.”

The press release touted Cotton’s leadership in helping advance educational opportunities, fostering student success, expanding career and technical programs and improving open and transparent communications.

Cotton is a graduate of Great Bridge High School. He earned his bachelor’s degree at Old Dominion University and his master’s and doctorate degrees from George Washington University. He has been in education for more than 30 years, having begun his career as a fifth-grade teacher at Crestwood Intermediate School.

Chesapeake, VA – Chesapeake Public Schools (CPS) announces the retirement of Superintendent Dr. Jared A. Cotton, effective July 1, 2026. Dr. Cotton has served as Superintendent since July 2018 and has led the district with distinction, leaving a legacy of innovative leadership, academic excellence, and community engagement.

A Legacy of Leadership for Learning

Under Dr. Cotton’s visionary leadership, CPS has made significant progress in advancing educational opportunities and fostering student success. He spearheaded the development of the CPS strategic plan, Empower 2025, which has guided the district's priorities and progress during his tenure. This focus has led to pass rates that surpassed the state in all content areas and increased graduation rates. The implementation of the Leadership and Learning Framework improved instructional practices at all levels, while the transition to a one-to-one device program and the launch of the Chesapeake Virtual Academy (CVA) ensured K-12 students had access to high-quality virtual learning opportunities.

Career and technical education programs saw expansion during Dr. Cotton’s time with the division, including advanced initiatives like the Peake Café, an advanced culinary program that provides students with work-based learning experiences. At the middle school level, he introduced Computer Science and Student Leadership courses and developed a Computer Science Academy, SmithTech, at Oscar Smith Middle School, the district’s only Title I middle school. Elementary education also experienced transformative changes, with the addition of 17 art teachers and the introduction of elementary STEAM lessons to promote creativity, computer science, and design thinking. Furthermore, Dr. Cotton increased planning time for elementary teachers and adjusted the school calendar to support instructional excellence. His efforts were recognized with the 2023 Workforce Innovation Award for groundbreaking work-based learning opportunities.

Commitment to Communication and Community

Dr. Cotton prioritized open and transparent communication with stakeholders, resulting in a range of enhancements. Innovative tools such as social media channels, the "Amplified" podcast, and redesigned district and school websites were launched to improve outreach. He established the Family and Community Engagement (FACE) Office, which provides resources like Peake Parent University, providing families with access to a variety of events and workshops that enhance the academic progress of students and empower parents to become partners in their student’s educational journey. The district’s commitment to military families was highlighted by achieving recognition as the first school division in Virginia to have 100% Purple Star-certified schools. Ultimately, Dr. Cotton’s efforts in communication earned CPS the 2022 Communication Technology Award from the National School Public Relations Association (NSPRA).

Through annual State of the School System addresses and regular Superintendent’s Community Engagement Council meetings, Dr. Cotton maintained a strong connection with the community. These initiatives ensured stakeholders were informed and involved in the district’s progress.

A Career Dedicated to Excellence

Dr. Cotton’s contributions to education extend beyond Chesapeake Public Schools. He has held leadership roles at the state and national levels, including serving as Senior Coach for the Virginia Association of School Superintendents (VASS). His expertise has been sought after at prestigious conferences such as the National School Public Relations Association and the Virginia Association of Elementary School Principals, where he has shared insights on leadership, change management, and innovation in education. Dr. Cotton has also been a mentor to aspiring superintendents, helping to shape the next generation of educational leaders.

Additionally, Dr. Cotton’s dedication to professional growth has been demonstrated through his participation in programs such as Digital Promise and Transformational Leadership through InitiativeOne. His collaborative work with organizations such as the ACCESS College Foundation, United Way, SECEP, and the Governor’s School for the Arts reflects his commitment to building partnerships that enhance educational opportunities for all students. His leadership has not only benefited CPS, but has also made a lasting impact on the broader educational community.

Looking Ahead

“Serving Chesapeake Public Schools has been the honor of my career,” said Dr. Cotton. “Together, we have achieved incredible milestones that have enriched the lives of our students, families, and community. I am deeply grateful for the support of our dedicated staff, school board, and partners who made our vision a reality.”

“Dr. Cotton has led Chesapeake Public Schools with integrity, compassion, and a relentless focus on what matters most, our students,” said School Board Chair Angela Swygert. “His ability to unite people around a shared vision for excellence has made our school system stronger and more connected to the community we serve. We are sincerely thankful for his leadership during some of the most trying times in history. Dr. Cotton leaves behind an undeniable legacy of success and innovation.”

The Chesapeake School Board will announce plans for the selection of Dr. Cotton’s successor in the coming weeks. In the meantime, the district plans to celebrate his outstanding service and lasting impact.

About Chesapeake Public Schools

Chesapeake Public Schools is committed to providing students with a high-quality education in a safe and nurturing environment. Serving over 40,000 students, CPS is recognized for its innovative programs, dedicated educators, and strong community partnerships.