Theo Epstein left the Red Sox to join the Chicago Cubs in hopes of replicating the success he had in Boston, where he delivered two championships to a team steeped in history yet long without a World Series title.
His new team, however, is on pace to set a franchise record for losses, and his former club is hovering below .500 this late in a season for the first time in a decade.
In this rare matchup between two of baseball's most recognizable franchises Friday at Wrigley Field, the Red Sox hope to get back to the break-even mark while the Cubs' Ryan Dempster looks to extend a 15-inning scoreless streak.
Epstein took over Chicago's front office - and a major rebuilding project - following Boston's epic September collapse last year, leading to a lengthy saga about what the Red Sox would get as compensation. Boston also interviewed Dale Sveum twice for its managerial opening before he was hired by the Cubs.
It just so happens the Red Sox (31-32) are now making their first trip to Wrigley since 2005, when the then-defending World Series champions dropped two of three. Boston, which won its second title with Epstein as general manager in 2007, arrives on Chicago's North Side this time tied for last in the AL East.
A beleaguered rotation has been perhaps the biggest problem, with Boston's starters ranking 27th in the majors in ERA at 4.83. The Red Sox, who are under .500 after May for the first time since the final week of the 2001 season, are hopeful Daisuke Matsuzaka (0-1, 7.20 ERA) can help strengthen the rotation, and he showed some promise in his first start of the season.
Almost exactly one year after Tommy John surgery, Matsuzaka allowed four runs and five hits in five innings of Saturday's 4-2 loss to Washington. The right-hander, who has struggled mightily with walks throughout his MLB career, issued one free pass while striking out eight.
"Every time you pitch you want to give your team a chance to win," he said through an interpreter. "But I think I did leave some positives for my next start."
Facing a Chicago team that ranks 28th in the majors in runs scored (233) and 27th in on-base percentage (.304) should also help Matsuzaka's confidence.
The Cubs (21-42) lost to Detroit 5-3 on Thursday for their 22nd defeat in 28 games. They don't have many intimidating bats in their lineup aside from Alfonso Soriano, who is batting .359 with four home runs and 10 RBIs during a 10-game hitting streak and leads the majors with 12 homers since May 15.
Boston, meanwhile, is second in runs with 319, but was slumping until pounding out 14 hits in Wednesday's 10-2 win at Miami. The Red Sox had plated 12 total runs while losing four of their previous five.
"We need to score some runs," said David Ortiz, who hit his 15th homer Wednesday and had three RBIs. "We've been a little short doing that. We needed that."
Adrian Gonzalez chipped in with three hits to snap an 0-for-16 drought, and Scott Podsednik had two hits to bump his average to .373 in 16 games. Each could be poised for another big game.
Gonzalez is batting .385 with five homers in his last seven games at Wrigley, while Podsednik is 7 for 18 with a homer, a triple and two doubles against Dempster (2-3, 2.31). Gonzalez is 2 for 14 lifetime against the right-hander, but both hits were homers.
After going 18 straight starts without a victory, Dempster has won his last two outings in impressive fashion. He may not be with the Cubs much longer, however, with several teams in need of pitching and Chicago on pace to post the worst record in the history of a franchise that has not won the World Series since 1908.
His stock is also high considering he has yielded two runs or fewer in eight of his 11 starts, allowing seven hits and a walk over 15 scoreless innings in his last two.
The 35-year-old Dempster hasn't made a start against Boston since 2001, while with Florida.