Complex sentence: A number of former associates of the Waltham Watch Company and Chicago watchmaker J.C. Adams had discussed forming the first large watch company in the Midwest, and after a trip to Waltham, Massachusetts, Adams approached former Mayor of Chicago Benjamin Wright Raymond as an investor.
Split into simpler sentences: A number of former associates of the Waltham Watch Company and Chicago watchmaker J.C. Adams discussed forming the first large watch company in the Midwest. After a trip to Waltham, Massachusetts, Adams returned to Chicago and approached former Mayor of Chicago Benjamin Wright Raymond as an investor.