His name is similar to that of his grandfather, Bobby Estalella (1911 – 1991), a Cuban professional baseball outfielder who played in the big leagues between 1935 and 1949.

In nine seasons, Estalella played for the Philadelphia Phillies (1996–1999), San Francisco Giants (2000–2001), New York Yankees (2001), Colorado Rockies (2002–2003), Arizona Diamondbacks (2004) and Toronto Blue Jays (2004).

He was signed by the Cincinnati Reds to a minor league contract before the 2005 season but chose free-agency during spring training.

In Aug 2010 had hip surgery and have been denied the opportunity to rejoin a team after extensive rehab.

(48 HR; 195H) Estalella was linked to the BALCO steroids scandal through leaked testimony.