Steve DeBerg (49ers 1978-80, Chiefs 1988-1991)
All right, DeBerg might have had a few stops between his excursion from San Francisco to Kansas City. But we know who hastened his departure in San Francisco, right? (Well, if you're stumped, just flip ahead to the next slide.)
Joe Montana (49ers 1979-1992, Chiefs 1993-94)
Montana established himself as one of the greatest (if not the greatest) quarterbacks in NFL history during his time with the 49ers. The Chiefs acquired him to push a perennial playoff team over the top. And Montana nearly did it. Nearly. Montana led the Chiefs to back-to-back playoff berths, but lost in the playoffs both times without reaching the Super Bowl. In fact, Montana led the Chiefs to the 1993 AFC Championship Game before ultimately losing to the Buffalo Bills.
Steve Bono (49ers 1989-1993, Chiefs 1994-96)
Bono once served as Montana's backup in San Francisco and then ended up as his backup in Kansas City in 1994. After Montana's retirement, Bono assumed the starting quarterback job for the Chiefs and led the team to a 13-3 mark in 1995, best in the AFC. But Bono and the Chiefs had a disappointing loss to the Indianapolis Colts (and current 49ers coach Jim Harbaugh) in the divisional round of the playoffs.
Elvis Grbac (49ers 1994-96, Chiefs 1997-2000)
Grbac joined the Chiefs in 1997 and he played well during his 10 starts that season, but ultimately fell short in the playoffs (are we sensing a pattern?). Grbac offered a mixed bag for the Chiefs during his tenure; his standout year came in 2000 when he passed for 4,169 yards and 28 touchdowns. Grbac parlayed that success into a big-money deal with the then-Super Bowl champion Baltimore Ravens in 2001.
Jon Ferrey/Associated Press
Alex Smith (49ers 2005-2012, Chiefs 2013-)
Smith does have a 49ers legacy to live up to in Kansas City. All of the aforementioned quarterbacks did lead the Chiefs to the playoffs at one point. With Andy Reid at the helm and a roster featuring six Pro Bowlers in 2012, it's not out of the question for the Chiefs to contend in the AFC West this season. The key question is if he can be the quarterback to finally take them back to the Super Bowl.