Johnnie-Owned Businesses in Maryland Give Back at the 41st Annapolis Cup
April 18 | By Kirstin Fawcett (AGI26)
Macarena Olsen (A13) wryly recalls never feeling quite at home in Southern Florida, where she spent her adolescence. “There was a lot of beach volleyball and sun,” she says. “And I would secretly go and read Nietzsche or something.”
The closet bookworm eventually wound up in Annapolis by way of said philosophers, where she met her husband, local resident Jeremiah Olsen (A11), and forged lifelong friendships through St. John’s College. A recurring highlight of their close-knit community has always been the annual spring Annapolis Cup croquet match against the Naval Academy, which fell this year on Saturday, April 5.
Replete with swing dancing, big band music, and even bigger hats, the friendly rivalry culminated in a rare victory for the midshipmen, with the afternoon’s final face-off resulting in a 3-2 upset against the Johnnies. But the occasion’s significance for Olsen went beyond the scoreboard: After attending every Annapolis Cup since freshman year, her family-owned winery, Casa Carmen, was serving as an event sponsor.
“It’s such a fun day,” says Enrique Pallares, Olsen’s brother and a Casa Carmen business partner. “It’s a great celebration with such interesting history, and it really shows the Johnnie character through and through.”
Croquet at St. John’s is a beloved tradition while also existing as the college’s largest community event. Though the event is not a fundraiser, donations generated during the event and the Johnnie Day of Giving the same week go toward maintaining the Program’s affordability, and sponsorships with local businesses help guarantee that the celebration remains free for current students (Johnnies and midshipmen alike) and discounted for alumni returning to campus.
Sponsors, in turn, receive increased visibility and brand awareness while ensuring the continued success of a popular hometown event. In the case of Johnnie-owned businesses in the region like Olsen’s, there is the added benefit of giving back to one’s alma mater in an especially meaningful way.
Johanna Wilson (A90) and Richard Smith (A90), who co-founded pioneering mobile apps company OpenPath Products in Annapolis in 2001, attended their first croquet match against the Naval Academy as students in 1987. “There were far fewer people, but there was a very nice vibe,” Wilson says. “People dressed up.”
The 2025 Annapolis Cup marked OpenPath’s first time sponsoring the event. Wilson and Smith have lived in Annapolis since their mutual college graduation, and they sought with croquet this past April “to encourage some tradition, and the civility that we think it brings with it,” Wilson says. “I don’t think the Naval Academy has a huge number of opportunities to interface with us as Johnnies. It’s good for both parties to reach across the street and be able to shake hands and enjoy themselves.”
It was also the first year that Casa Carmen, which maintains a tasting room on the Eastern Shore and a vineyard near the Maryland-Pennsylvania border, served as an event sponsor, with an in-kind donation of their signature dry wines. (Olsen, who lives locally in Annapolis, handles the brand’s graphic design and branding.)
April 2025 may have marked the beginning of the two companies' involvement in croquet, but Wilson, Smith, and Olsen all have long histories of alumni stewardship with St. John’s College. Wilson has served as a BVG member for the past six years while Olsen had stints on the Alumni Association Board and Alumni Giving Council before joining the Advisory Council of the Mitchell Art Museum. OpenPath, meanwhile, has established a reputation since its inception 25 years ago as a flagship employer for tech-inclined St. John’s College graduates. “We’ve hired a number of Johnnies,” Wilson says, “and many of them have been at OpenPath for many, many years.”
Casa Carmen, in contrast, is a true family production, as it’s co-owned and operated not just by Olsen but her two brothers, Enrique and Felipe Pallaras; their parents, Silvia and Enrique Sr.; and Olsen’s sisters-in-law, Laura and Jane. But the winery is also a true product of a liberal education: Several members of the family, in addition to Olsen, received Great Books degrees, and Enrique Jr. even worked part-time at St. John’s while completing PhD coursework at Catholic University.
It’s no surprise then that a Johnnie-esque mentality permeates Casa Carmen’s product, from the names (the “Tender is the Night” vermouth draws inspiration from F. Scott Fitzgerald) to the co-founders’ love of philosophy and their interdisciplinary appreciation of the winemaking craft. And before Casa Carmen, before the siblings’ respective Great Books diplomas, there was always the Annapolis Cup. “We love St. John’s, and we want to support it and see it thrive,” says Olsen, “whether through croquet or really anything.”
Along with revisited nostalgia, strengthened community ties, and money raised for the Program, an added benefit of the Annapolis Cup for Wilson and Smith is that it never fails to provide an invigorating challenge for a close family member of theirs: Smith’s father, a resident at Ginger Cove retirement community in Annapolis, plays on the facility’s team—which, every year, competes against both the Naval Academy and St. John’s College in the lead-up to the big match. “The Ginger Cove team members have far more experience,” Wilson laughs. “So, guess who always wins?”
Are you a business-owning Johnnie who is interested in sponsoring the Annapolis Cup in 2026? Learn about opportunities on our website and contact with questions.