Ortiz, who stands as Theo Epstein's biggest acquisition during the Cubs president's decade as an executive with the Boston Red Sox, blames the one thing many Cubs fans cherish -- the one thing that sets the Wrigley Field experience apart.
"Through the years I've talked to a lot of friends of mine that have played for the Cubs," Ortiz said Tuesday night before the Red Sox lost 2-1 to the Cubs in the second game of a three-game series at Fenway Park. "The one thing that everyone talked about was the schedule in Chicago. They get excited walking into a city that's based on baseball, but once they start dealing with the schedule it kind of mentally wears you down."
Ortiz cited former Cub Alfonso Soriano among others who haven't liked the mixed schedule of day and night games.
When the team first installed lights in 1988, the Cubs were limited to 18 night games due to their stadium being in such close proximity with the neighborhood. Over the years the city had increased the number to 30 and for the first time in 2014 the Cubs have 38 scheduled night games.
"Believe it or not that's one of the biggest issues for that organization to become a winning ballclub," said Ortiz, who signed as a free agent with Epstein and the Red Sox in 2003 after six years with the Twins. "When you come down to the Cubs' schedule it's a game-changer, believe it or not. They play so many day games at home and then they have to travel to another city and adjust themselves to the night games."
Because of national television commitments the Cubs play noon and 3 p.m. games at home in addition to their normal 1:20 p.m. and 7 p.m. start times. For the first time in years they were allowed to schedule 3 p.m. games on Fridays due to late travel issues on many Thursdays.
"If the rest of the league had the same schedule that you have it's fine," Ortiz said. "But once you play day games for about a week and next thing you know you have to go into a city and play night games, then the next thing you know you have to go to the West Coast and adjust to the time there, then you have to come back home and start playing day games, it's too hard for baseball (players)."
The Cubs are in a rebuilding phase that has resulted in an influx of young players who would seemingly better handle the rugged schedule than aged veterans, though management has conceded success will only follow when it's the right fit for players regardless of experience.
Clearly, though, the Chicago nightlife has taken down more than one career over the years.
"You can throw a group of young guys out there to figure it out but you need a veteran in the mix," Ortiz said. "If the Cubs want to do something different about winning ... to begin to win a championship, they have to make adjustments based on that."