DeMarco: No quick fix for these Red Sox Payroll flexibility is nice, but Boston won't contend until at least 2014 By Tony DeMarco updated 7:52 p.m. Baseball Expert Tony DeMarco has been covering the big leagues since 1987, and been casting Hall of Fame ballots for the last 15 years. He answers questions weekly here: Q: The Red Sox now have payroll flexibility, but it looks like their competitiveness has been damaged. Realistically, how long will it take for the team to become a powerhouse again? - Art Shannon, Coronado, Calif. A: It's been a disastrous season in Boston to say the least, and the Red Sox are looking at their first last-place finish in 20 years, and only the second since 1932. Not to mention the game's worst wins/payroll ratio, as they had a $175-million payroll before the big deal with the Dodgers. What's clear now is that everything 'Theo' is being dumped, and it's Ben Cherington's team now. That probably doesn't bode well for Bobby Valentine, either. But no matter who's managing in 2013, the Red Sox will look much different. They'll have to make decisions on David Ortiz and Jacoby Ellsbury, both eligible for free agency, and at this point, you have to think they'll bring them back. But that won't be the case with Daisuke Matsuzaka and James Loney, two more free-agents-to-be. In fact, the rest of this season is in effect a tryout for much of the roster besides the obvious key regulars, led by Dustin Pedroia and injured Will Middlebrooks. Is Jose Iglesias the shortstop of the future, for instance? Jon Lester, Clay Buchholz and likely John Lackey will be back in the rotation, but at least several spots on the pitching staff also are in question for 2013. The good news is that with about $250 million freed up in the Dodgers' deal, the Red Sox can maneuver in the off-season. This, however, is not a great winter for free agents beyond Josh Hamilton (if he reaches free agency). Most likely, this is not a one-year fix, and so Cherington's focus should be on a return to prominence that has the capability to last a few years. I'd say 2014 at the earliest for the Red Sox being a legitimate postseason threat. Q: Who do you like for the National League Rookie of the Year Award? Could you have a little love for the Cardinals' Matt Carpenter? - Stephen Shoemaker, Tulsa A: It's a duel down the stretch between Cincinnati's Todd Frazier and Washington's Bryce Harper, with Arizona's Wade Miley lurking - making this yet another season that convinces me there should be Rookie hitter of the year and Rookie pitcher of the year awards in each league. Frazier and Harper each had 18 homers through Monday, and both have been very versatile defensively, playing multiple positions on likely division winners. Frazier has solid advantages in RBI, batting average, slugging percentage and OPS; Harper in runs scored and stolen bases. Miley clearly has been the league's best rookie pitcher, going 15-9 with a 3.07 ERA and 163 hits allowed in 170 innings, pitching half the time in hitter-friendly Chase Field. In some order, those three likely will be on most ballots. Other notables include the Cubs' Anthony Rizzo, who's finishing strong; Milwaukee's Michael Fiers, who has slid under the radar at 9-7-3.05; Frazier's teammate Zack Cozart, and Colorado's Wilin Rosario. But in the latter case, his defensive struggles finally have come to national attention with a recent benching as his passed ball total rose to an alarming 18. This has been going on all season, but the breaking point finally was reached with a four-passed-ball game in Philadelphia over the weekend. Carpenter has made a nice contribution to the Cardinals' league-leading offense, hitting just over .300 - the highest by an NL rookie - in part-time duty. But given the rest of the field, he isn't likely to get any top-three votes. And while we're on the subject, how about the AL field - one of the best in memory: League MVP candidate Mike Trout, Oakland's Yoenis Cespedes (as well as Jarrod Parker, Ryan Cook and Tommy Milone), Texas' Yu Darvish, Tampa's Matt Moore, Seattle's Jesus Montero, Boston's Will Middlebrooks and Baltimore's Wei-Yin Chen. Q: The St. Louis Cardinals presently have five .300 hitters in their lineup. Have there been teams at the end of a season with more .300 hitters? - Larry Gyuricza, Palatine, Ill. A: Multiple .300 hitters in a lineup was a very common occurrence in the game's slugging era of the late 1920s-1930s. In fact, according to Baseball-Reference.com, a total of 26 teams had as many as six .300 hitters in a season between the 1920 and 1938 seasons. Four teams in the 1920s had seven .300 hitters, and the 1930 St. Louis Cardinals had all eight regulars hit at least .300 and batted .314 as a team on their way to an NL pennant. Alas, they lost the World Series to the Philadelphia A's. Moving to more-modern times, the Steroids Era of the late-1980s to early-2000s also saw a proliferation of lineups with multiple .300 hitters. But the only team with six .300 hitters in the same lineup - all of whom with enough plate appearance to qualify for the batting title - was the 1995 Cleveland Indians: DH Eddie Murray, LF Albert Belle, 2B Carlos Baerga, 3B Jim Thome, CF Kenny Lofton and RF Manny Ramirez. Sandy Alomar Jr. also hit exactly .300 in 218 plate appearances, as he platooned behind the plate with Tony Pena. Three teams in the late-1990s had five .300 hitters in their lineup, including one I covered as a beat writer - the 1996 Colorado Rockies. Given the asterisk of playing in pre-humidor Coors Field, they also amassed 221 homers and 201 stolen bases. The five .300-plus hitters were Ellis Burks, Eric Young, Dante Bichette, Andres Galarraga and Vinny Castilla. The 1997 Red Sox (Nomar Garciaparra, Mo Vaughn, John Valentin, Troy O'Leary, Reggie Jefferson) and 1999 Mets (Edgardo Alfonzo, Mike Piazza, Rickey Henderson, Robin Ventura, Roger Cedeno) also had five. So did the 1976 Big Red Machine (George Foster, Joe Morgan, Pete Rose, Ken Griffey Sr., Cesar Geronimo).