The Gators (16-3-2 overall, 11-0 in conference) won their last championship in 1994 -- before the IAAM was formed.
The rest, as they say, is history as Jester was drafted into the varsity head coaching position six years ago and has worked to improve the team's record every year. In 2008, Seton Keough had seven wins.
"In the last five years, we've won 63 games," Jester said. "Before that, the school hadn't won an IAAM conference game in at least five years. They've been the doormat."
Now they live in the penthouse.
"We've been trying to build our program," Seton Keough athletic director Josiah LaTona said. "Tom does an excellent job and [assistant coach] Tabatha [Zimmer] has extensive playing and coaching experience, and they both take part in club level programs."
Five of the nine seniors on the team are committed to or considering Division I, II or III schools: Ciara Saunders is going to Missouri State; Kathleen Sigwart to Limestone; Anna Stumme to Catholic, Alsiha Locklear to Frostburg; and goalie Becca Wallace is still deciding among a handful of Division I and III schools.
"They have a program here that is a combination of teaching girls from scratch and also picking up girls who played prior, and they've mixed in good athletes to have a nice product," LaTona said.
This season, the team has scored 44 goals in the conference and allowed none. They are on an 11-game shutout streak. Outside of the conference, the Gators tied No. 2 South River, 0-0, and No. 10 Century, 1-1 (Century had to come from behind to tie in the final seconds). Their only losses were to No. 7 Broadneck, 1-0, No. 8 Archbishop Spalding, 1-0, and No. 12 C. Milton Wright, 2-0.
"I was intent on us running a hard road before we got to B Conference play this season," Jester said. "But it was frustrating to come that close to beating those top teams. If we could have gotten just one. The Century game, we were dominating that game, but then with 20-30 seconds left, a wide shot went in. It was deflating."
But the very fact Seton Keough is competing at this level, Jester continued, is uplifting. When he took over the program, it was on the brink of extinction. Now he has a experienced assistant coach in Zimmer, who Jester said has been key to the team's success this season because of her knowledge.
It also helps to have a roster full of players who play outside the school for U19 teams, club teams and also were members of the Disney College Showcase team that finished with a silver medal last February.
"It's difficult to build this and to continue this," Jester said. "There are no feeder schools like Garrison [Forest], Bryn Mawr and [Notre Dame Prep] have. They have their players coming through their middle schools. We have some players coming in now from Anne Arundel County, where there are some good rec programs.
"I actually think I have another couple of years with some solid players here. We have some solid juniors and some super sophomores, a core group of four -- Zoe Smith, Emily Lemanski, Katie Audino and Sarah Asseng. That core will serve us well, and I think we'll be able to maintain a top 3 position."
This season, Hannah Tavik, Emani Byrd, Kathleen Sigwart and Lemanski have been described by Jester "as a brick wall" of defense. Offensively, it's also hard to shut down the Gators who get goals from all over the field with Saunders, Asseng, Audino, Alisha Locklear, Stumme and others contributing.
Now comes the playoffs, and Sigwart, one of those staunch defenders, thinks the team will continue to do well in the postseason.
"I think just the fact we work so well as a team on and of the field is part of our strength," Sigwart said. "Some of us seniors have been playing together four years and I think we're playing harder because we don't want to lose."
Sigwart was sidelined during the season-ending game at John Carroll because the nail on the middle finger of her right hand was completely ripped off during a game at Maryvale Prep on Oct. 16. She needed seven stitches to close up the tear and also suffered a chip fracture at the top of the finger bone. But Sigwart is expected back for Tuesday's game.
"It is so cool to be at the top of the B Conference," she said. "It's the first time it's ever happened since we restarted our program six years ago. We're finally first."