David Ortiz led off the fifth inning Saturday night against the Tampa Bay Rays’ Matt Moore with 499 homers, and ended the at-bat as a part of baseball’s elite. Ortiz crushed a 2-2 breaking ball into the right field bleachers for his 500th career home run after hitting his 499th career round tripper in the first inning.

Ortiz becomes the 27th player in the history of Major League Baseball to accomplish this feat. He also joins a group of legendary Red Sox batters who have hit their 500th homer with Boston, those players being Jimmie Foxx, Ted Williams and fellow Dominican Manny Ramirez. Ortiz is just the fourth player from the Dominican Republic to hit 500 homers, continuing a strong year for Boston’s Dominican born, after Pedro Martinez was inducted into the Hall of Fame earlier in the summer.

While this season has been another disappointing display for the Red Sox, Ortiz has been one of a few bright spots in the 2015 season. His three-month power surge has been one of the best in his career, hitting 28 homers in 273 at bats, a better home run to at a bat ratio than his 54 home run season back in 2006. With this display of power at age 39, Ortiz is making a bid to have his contract extended.

At the beginning of the 2015 season, Boston and Big Papi agreed to a one-year $16 million contract extension, with an option to keep him in a Red Sox uniform until the 2017 season. He would be 42 then, but Ortiz has showed little signs of slowing down.

This is Papi’s ninth season with 30 or more home runs, passing Williams for the most in Red Sox history. He is proving that he can still compete in his advanced age, and has been a staple of the Boston offense for over a decade.

But the question that remains unanswered is: Should he retire? Any Sox fan would tell you they want Ortiz to retire as a member of the Red Sox, Ortiz probably wants the same thing; but would getting rid of Ortiz be better for Boston with their current log jam of a roster?

Moving Hanley Ramirez out of the outfield has become the next course of action for Boston, opening up that spot to young players like Jackie Bradley Jr., Mookie Betts and Rusney Castillo. Moving Hanley to first base was an option as well, but with players like Travis shaw coming up from Triple A and having success, relegating Ramirez to designated hitter duties makes sense.

Since Ortiz is showing that he can still hit, this problem becomes a lot tougher. Do the Red Sox keep Ortiz in as DH and let Hanley Ramirez flounder in the field and at the plate, taking playing time away from younger players who are having success? Or do they bench or trade Ortiz to make changes on the field and face the wrath of an angry Red Sox Nation?

After the Jon Lester debacle, if the Sox traded Ortiz now the city would probably implode, as he has been the most influential player for the Red Sox since joining the team in 2003. There are plenty of moves to be made for when Ortiz leaves, it is just a matter of time before he does. The only way for him to leave peacefully is for him to retire, but that might not be like until his contract is up in 2017.

As for what happens to Oritz after he does retire, Hall of Fame comes to the minds of many. Big Papi is arguably the best DH of all time, and his postseason numbers are staggering. He has been the most clutch hitter for Boston, entering the national spotlight in the latter stages of the 2004 postseason.

While Ortiz’s numbers are Hall of Fame worthy, many cite PED use in 2003 as a reason why he should be kept off the ballot. Ortiz claims innocence, and has not failed a drug test since 2004 when most of his power hitting was done.

Only time will answer these remaining questions about the extremely successful career for the Boston DH. Best case scenario for both him and the Sox? He retires at the end of next season, has his number 34 retired by the Red Sox, and will be a first ballot Hall of Famer. To end a career like his in such a way seems only fitting.