Ms. Softball 2022: Jessica Oakland

Jessica Oakland, the 2022 Ms. Softball State Player of the Year, stands with CIF NorCal D1 title trophy as the outfield fence that she hit so many home runs over looms in the background. Photo: Harold Abend / Cal-Hi Sports.

Hitting a state-best 21 homers for the No. 1 team in the state helps St. Francis of Mountain View standout to get over the top in this year’s Ms. Softball State Player of the Year honors. The daughter of head coach Mike Oakland also had 40 homers in the last two seasons and gained several other state record category qualifying marks. She’ll also now be forever compared to the last Ms. Softball from the CIF Central Coast Section.

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In one of the most difficult choices over the past several years between two outstanding and worthy candidates, it boiled down to one of the five finalists edging out the other with numbers that were just too hard to overlook.

The result is that Jessica Oakland of State Team of the Year and final No. 1 ranked St. Francis (Mountain View) has been named the 2022 Ms. Softball State Player of the Year after edging out Micaela Kastor of Oaks Christian (Westlake Village) for the top high school softball honor in the Golden State.

In winning the Ms. Softball State Player of the Year award, Oakland becomes only the second player from the CIF Central Coast Section to be honored dating back to the inception of Ms. Softball for the 1974 season. The other winner from the CCS was the great Keilani Ricketts of San Jose Archbishop Mitty. Ricketts was the 2009 honoree.

“Thank you so much for this award. It really means a lot to me,” said Oakland when told she was being named Ms. Softball.

Mike Oakland moved from coaching baseball at St. Francis of Mountain View to softball when his daughter, Jessica, began to star in the sport. Photo: Mark Tennis / Cal-Hi Sports.

Besides Ricketts, the Minnesota-bound Oakland is only the fourth player from Northern California to win the honor since 2006 when Amanda Williams of Freedom (Oakley) was the winner. The other two were Johanna Grauer of Pleasanton Amador Valley in 2014 and last year’s winner Jayla Castro of Rocklin. Overall, since 1974 Oakland is only the 10th player from north of Fresno to be named Ms. Softball

When those names were mentioned to Oakland along with 2019 winner and current Oklahoma star Kinzie Hansen of Norco, and legendary UCLA coach Lisa Fernandez, the 1989 winner when she played at Lakewood St. Joseph, plus others, Jess showed a little humility.

“Being able to represent the CCS and Northern California is so cool and truly amazing,” said Oakland, who is known as “Jess” by family, coaches, teammates and the entire Lancers community. “Some of those names on the list are legends in the softball community and people I have looked up to as a young girl – and it’s really cool to think that my name is being put up there with them.”

“As a young softball player there were high school players like Keilani Ricketts that I looked up to and wanted to be like,” Oakland continued. “And I’m hoping that I can be like that to other young softball players.”

Oakland’s Ms. Softball qualifications are putting up some record-setting numbers on a team that played at the highest level. As mentioned, the Lancers didn’t win the Michelle Carew Classic, nor did they win the Livermore Stampede, but they swept West Catholic Athletic League arch rival and state No. 8 Mitty to win the league and the CCS Open Division championship. Then, after a quarterfinal victory, the Lancers reversed a loss to state No. 5 Sheldon (Sacramento) at the Livermore Stampede with a 4-0 victory in the CIF Northern Regional Division I semifinals, a game in which Jess blasted home run No. 21 on the season. From there, the St. Francis shortstop had a double that drove in two runs in the Lancers’ 6-0 victory over state No. 6 Clovis in the NorCal D1 title game.

On the season, Oakland had a .578 batting average and a .678 on-base percentage. She hit 21 home runs with three triples, eight doubles, and had 67 RBI and 52 runs scored. Jess had a whopping 1.433 slugging percentage and 2.114 OPS percentage. In 119 plate appearances, Jess only struck out eight times while drawing 27 bases on balls and two hit batters.

For a solidly-built girl who stands 5-foot-10, she flashed good speed and even stole six bases. On defense playing shortstop against the top teams in the state that had players that could put a charge in the softball, Oakland had a .914 fielding average.

The 21 home runs was the leading reported mark in the state. The 67 RBI was the No. 4 mark in the state with no girl above her playing on a state ranked team. The 52 runs scored was No. 11 in the state with the only girl from a ranked team ahead of her being Ms. Softball finalist Dakota Kennedy of Sheldon. The 1.433 was No. 14 in the state but once again the highest of any player from a ranked team.

With respect to the Cal-Hi Sports Online Record Book, Oakland already has three spots from last season when she was also a Ms. Softball finalist and the State Junior of the Year. The 19 home runs she hit led the state last year as well and tied her for the No. 8 spot all-time in the Record Book on the Most Home Runs (Season) list. Oakland also had 55 RBI last season and that makes the Most Runs Batted In (Season) list, and her 50 runs scored makes the Most Runs Scored (Season) list as well.

The 21 home runs this season ties her for fourth all time on the season list and the 67 RBI comes in high up on that list as well. The 52 runs scored also gets Jess a second spot on that list.

For her career, Oakland hit 44 home runs in four varsity seasons but in the 2019-20 season that was wiped out by the pandemic she only played one game as a sophomore, but you guessed it, she hit a home run and drove in two. Even so, the career home run mark has her among the top 15 players all time on the Most Home Runs (Career) list. The same goes for runs batted in. With 35 as a freshman, Oakland finished her career with 159 RBI and that’s good enough for a top 25 spot on the Most Runs Batted In (Career) list. Last but not least her 135 runs scored also qualifies Oakland for a spot on the Most Runs Scored (Career) list. All of these records are not yet posted on the Cal-Hi Sports site, but they will be before the 2022 football season gets going.

It would have been nice to see Oakland and Kastor of the CIF Southern Regional Division I champions square off in a state championship but with that not possible the nine spots Oakland has earned in the Online Record Book was just too much to not garner her the Ms. Softball honor.

As a junior, Oakland had one of the best seasons as a hitter and slugger in CCS history. She did even better as a senior. Photo:

We can’t mention all of her Lancers teammates but would be remiss if we didn’t mention catcher and Washington-bound Sydney Stewart, who along with Jess were also the top two players on the Lancers basketball team that made it to the CIF Northern Regional playoffs. Stewart hit 15 home runs and drove in 53 runs, with both marks making their respective lists in the Online Record Book. Stewart’s 31 career home runs gets her a spot on that list as well.

An interesting twist to the story has to do with her father and Lancers’ head coach Mike Oakland. After winning three CIF Central Coast Section titles as the St. Francis baseball head coach, he stunned a lot of people when in 2017, and knowing Jess was coming in 2018, he came over after winning the CIFCCS Open Division championship in 2016 to fill the softball opening of a team that hadn’t had a winning season in 10 years and was 0-12 in the WCAL in the 2016 season.

Now, with Jess as the centerpiece, his Lancers have won three CIFCCS Open Division championships in his five years at the helm and his daughter’s four year career. Remember, there was no championship in the 2019-20 season.

“Coaching Jessica the last four years has been the highlight of my life,” Coach Oakland remarked. “Jess has put in a tremendous amount of work to be the softball player she is today.”

“To be named Ms. Softball for the state of California is a crowning achievement for her,” continued Oakland. “I couldn’t be more proud of the person she has become.”

Even with all she’s done Jess wanted to talk about the team.

“All of us have been playing with and against each other since we were little, and all of us being able to combine our talents and play for St. Francis is amazing,” Jess said. “Every day we showed up to the field and we flat out competed, and that’s why we have had so much success the last couple of years.”

“A few years ago St. Francis softball was not what it is now,” Jess continued. “In fact, it had a string of losing seasons. So I think it’s really cool how my senior class and the classes below us have helped turn this program around into the Cal-Hi Sports State Team of the Year.”

Does she feel she has made herself a role model for future Lancers?

“I wanted to make a lasting impression at St. Francis and leave my mark, but I never thought I would be creating a legacy for other people to follow,” Oakland said. “Knowing that the underclassmen and the kids under them will know my legacy and try to follow in the future is such an amazing feeling.”

With all the accolades and big-time numbers, some softball aficionados questioned why Jess chose Minnesota rather than a big name program?

“My recruiting journey is very interesting because it was right in the middle of the COVID pandemic and everything was on the phone or over Zoom,” Jess said. “I felt like the Minnesota coaches did a fantastic job at navigating the difficulties, and they really made me as well as my family welcome.”

“They really made it a points to get to know me personally and mine as well as my family’s interests,” continued Jess, who had a final 3.82 GPA and plans on studying kinesiology when she becomes a Golden Gopher. “So when the time came to make a decision I knew what the right choice was. My mom (Dina Oakland) and I were able to go out to the campus by ourselves and take a look around. The second I stepped foot on the campus I felt at home and knew I had made the right choice.”

Not surprisingly, her desire to study kinesiology is part of her long-term plans.

“After softball is done I really want to come back and coach softball to the little ones and eventually work my way to high school and maybe even college,” Jess said.

Now, after garnering local awards such as the Bay Area News Group Player of the Year, plus others, Oakland has now won the grand prize.


Last year’s winner, Jayla Castro of Rocklin, is now at UCLA. Photo:

2022 – Jessica Oakland,
Mountain View St. Francis INF
2021 – Jayla Castro, Rocklin C
2020 – No selection (pandemic)
2019 – Kinzie Hansen, Norco C
2018 – Payton Tidd, San Marcos P-OF
2017 – Taylor Dockins, Norco P-DH
2016 – Nicole Bates, Ceres INF
2015 – Taylor McQuillin, Mission Viejo P
2014 – Johanna Grauer,
Pleasanton Amador Valley P-DH
2013 – Kylie Reed, Norco INF
2012 – Emily Lockman, Norco P
2011 – Lauren Sweet, Corona Santiago C
2010 – Jessica Hall, Chino Hills Ayala P
2009 – Keilani Ricketts, SJ Archbishop Mitty P-DH
2008 – Jessica Spigner, Valencia P-SS
2007 – Jordan Taylor, Valencia P
2006 – Amanda Williams, Oakley Freedom P
2005 – Katie Cotta, Linden P-DH
2004 – Anjelica Selden, Travis AFB Vanden P
2003 – Lisa Dodd, San Diego University City P-DH
2002 – Alicia Hollowell, Fairfield P
2001 – Marissa Marzan, Fresno Bullard P
2000 – Jamie Southern, Clovis, P-INF
1999 – Andrea Vidlund, Orangevale Casa Roble, P
1998 – Amanda Freed, Garden Grove Pacifica, P
1997 – Amanda Freed, Garden Grove Pacifica, P
1996 – Amanda Scott, Clovis P
1995 – Courtney Dale, Fresno Bullard P (Jr.)
1994 – Sara Griffin, Simi Valley P
1993 – Sara Griffin, Simi Valley P
1992 – Leah O’Brien, Chino Don Lugo P
1991 – Jennifer Brundage, Irvine P
1990 – Karen Jackson, Roseville P
1989 – Lisa Fernandez, Lakewood St. Joseph P
1988 – Michele Granger, Placentia Valencia P
1987 – Michele Granger, Placentia Valencia P
1986 – Michele Granger, Placentia Valencia P
1985 – Jackie Oakley, Huntington Beach Ocean View P
1984 – Samantha Ford, Newhall Hart P
1983 – Shawn Andaya, Lodi P
1982 – Kandy Foust, Santa Maria Righetti P
1981 – Tracy Compton, Santa Maria Righetti P
1980 – Tracy Compton, Santa Maria Righetti P
1979 – Mary Lou Ramm, Chula Vista Hilltop P
1978 – Teri Young, El Segundo P
1977 – Karen Andrews, San Diego Henry P
1976 – Jan Jeffers, Lompoc P
1975 – Barbara Reinalda, Cerritos Valley Christian P
1974 – Barbara Reinalda, Cerritos Valley Christian P

Harold Abend is the associate editor of and the vice president of the California Prep Sportswriters Association. He can be reached at Don’t forget to follow him on Twitter: @HaroldAbend

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