By Brendan O’Connell

This past week, the World Series champion Red Sox rolled through the streets of Boston to celebrate their fourth title since ending their 86-year drought in 2004. Scores of fans packed the city to thank the squad that overcame the 100-win New York Yankees, 103-win Houston Astros and defending National League champion Los Angeles Dodgers en route to parading around Fenway Park on duck boats.

The Red Sox’ postseason defied expectations and well-established narratives.

Despite underwhelming performances from stars Mookie Betts and Xander Bogaerts, many heroes emerged. ALCS Most Valuable Player and Gold Glove centerfielder Jackie Bradley Jr. provided timely hitting, World Series MVP and journeyman first baseman Steve Pearce took over the final two games of the year and young up-and-comer Rafael Devers drove in runs game after game.

The much-maligned bullpen stepped up after being considered the team’s Achilles heel heading into October. Even with closer Craig Kimbrel performing far less effectively than usual, the relief staff excelled. Cast-off Ryan Brasier and fireballer Matt Barnes each tallied 1.04 ERAs and goggle-sporting Joe Kelly all of a sudden showcased the most electric combination in the league with his triple-digit fastball, wafting changeup and snappy breaking ball. Rookie manager Alex Cora deployed starters in the 8th inning in brilliant fashion to bridge any gaps, with Nathan Eovaldi providing one of the most heroic losing efforts in history with 97 pitches in relief in the 18-inning Game 3 of the World Series.

With ace Chris Sale injured, Rick Porcello, Eovaldi and even Eduardo Rodriguez turned in solid starts time after time, while perennial playoff disappointment David Price flipped the script. After starting his career with an 0-9 record in his first 11 postseason starts, Price finished this October with three consecutive wins with starts of 6 or more innings allowing three or fewer hits and two or fewer runs – and did so on short rest.

With contributions coming from everywhere – on the mound, in the field and in the lineup – President of Baseball Operations Dave Dombrowski faces a difficult offseason.

The task of keeping this championship team a contender will be a tall task. Some roster moves are out of his control and have already been finalized. Price has opted in for the remaining four years and $127 million of his contract, but many other pitchers are free agents this winter. Kimbrel, Eovaldi, Kelly and other talented arms are on the market and will carry a high price tag after their impressive performances. Meanwhile, an aging and ailing Sale is entering the final year of his deal, and his status with the team is sure to be a topic of discussion in the front office.

Other tough decisions include whether or not to bring back veterans Pearce, Drew Pomeranz and Ian Kinsler. Complicating all these decisions is the fact that Boston has little to no wiggle room financially, with $215 million already tied up in next year’s payroll. Furthermore, emerging studs Betts, Bogaerts, Bradley Jr., Andrew Benintendi and others will all reach the market in the coming years, and Boston would surely prefer to re-sign them sooner than later.

The Red Sox’ farm system is largely devoid of MLB-ready prospects to replace the players they will inevitably lose from their roster. As the team finds itself up against the luxury tax – and ceiling of their budget – Dombrowski will have to prove his worth if the Sox are to maintain their edge over high-powered rivals like the Yankees and their current status of champions of baseball. What will they do?