One of my favourite sections of the site (even if I’ve never settled on the perfect name for it!), a look at all the Miss Massachusetts Teen USA titleholders who’ve gone on to compete at Miss USA or in other state pageants. It’s always inspiring to see where their journeys have taken them — whether they won a crown early on, competed once or twice and then hung up the heels or kept showing up year after year, showing persistence in their quest to walk the Miss USA stage.
Despite more former Teens competing in California than any other stage, very few of them have been home-grown California Teen titleholders and only one Cali teen has ever won the Miss title – Shauna Gambill, who in 1998 came very close to being the first to win both Miss Teen USA and Miss USA outright!
Remarkably, after a string of all but one of the 1991-1996 Miss California Teen USA titleholders competing in Miss, the next to compete was Miss California Teen USA 2010 Emma Baker. Six of the 2010s Teens have returned to compete in Miss but so far none has won a title.
Winner
1
Susie Castillo (1998)
Semi-finalist
1
Kristen Mastroianni (1987)
Top 8/10/11/12*
1
Jackie Bruno (2003)
* Where the semi-finalists are cut in multiple stages before the top 5 or 6
1995
1
Kristen Mastroianni (1987)
2003
1
Susie Castillo (1998)
2008
1
Jackie Bruno (2003)
2009
1
Alison Cronin (2005)
1980s
1
Kristen Mastroianni (1987)
1990s
1
Susie Castillo (1998)
2010s
0
Winners highlighted in italics. Stats may be inaccurate, especially for the 1980s & 1990s as I am reliant on newspaper archives which do not list all contestants.
1980s
1
Kristen Mastroianni (1987)
1990s
5
January Newcombe (1993), Erika Ewald (1995), Maria Menounos (1996), Jessica Gregory (1997), Susie Castillo (1998)
2000s
6
Monique Jones (2000), Amanda Birdsell (2002), Jacqueline Bruno (2003), Alison Cronin (2005), Caroline Lunny (2008), Katie Vatalaro (2009)
Massachusetts, California, Florida, Illinois
Winner
6
Kristen Mastroianni (1987), Susie Castillo (1998), Jacqueline Bruno (2003), Alison Cronin (2005), Caroline Lunny (2008), Annika Sharma (2020)
1st runner-up
4
Maria Menounos (1996), Monique Jones (2000), Amanda Birdsell (2002), Bailey Medeiros (2014)
2nd runner-up
2
January Newcombe (1993), Jessica Gregory (1997)
Non-finalist
1
Katie Vatalaro (2009)
