Weiss is 25 years old and was born in Providence, Rhode Island. The slugger would grow up in the Fort Myers area in Florida and was named the 2019 Fort Myers News-Press Baseball Player of the Year. Becoming a key member for Canterbury School and their three Class 3A state championships. Weiss would set the career and single season home run records. 

The infielder’s college career started at Coastal Carolina, he would transfer to Miami of Ohio and win the MAC Defensive Player of the Year award, and finish up in the SEC with Auburn. In his only year with the Tigers he starred in 52 games hitting at a slash of .291/.403/.487 and a .890 OPS. 

Weiss would sign as an undrafted free agent with the San Diego Padres in July upon graduating. This past season Weiss started with the Cleburne Railroaders playing in 80 games for Cleburne, he hit six home runs, had a .376 on-base percentage, and drove in 24 runners. 

Weiss would sign with the RailCats and make his debut against the Milwaukee Milkmen in Gary. In his first at-bat he would connect with a pitch and drive it over the right field wall for a solo home run. He would get a cup of coffee with Gary playing in nine games, hit at a .289 pace, with two home runs, and drove in seven runners.