Former Red Sox exec inks Phillies ace Zack Wheeler to historic extension



The Philadelphia Phillies continue showing their high-value players the money.

On Monday, they finalized an extension for Zack Wheeler, signing their ace to a three-year extension worth $126 million. The $42 million average annual value is an MLB record-breaking sum for an extension.

After beginning his career with the division-rival New York Mets, Wheeler came to the Phillies as a five-year, $118 million free-agent signing before the 2020 season. Since trading in the blue and orange for red pinstripes, the right-hander has been one of the game’s most dominant and durable starters: over his first four seasons in Philly, his 19.6 Wins Above Replacement outranks all Major League pitchers.

Wheeler owns a 3.06 ERA – fourth-best in the Majors since 2020 – and 1.055 WHIP across 101 regular-season starts for the Phillies, including three complete games and two shutouts, all during his ’21 All-Star season. Despite leading MLB with 213 1/3 innings pitched and the NL with 247 strikeouts and 7.7 WAR in ’21, he finished runner-up to Corbin Burnes – who owned the ERA title but whose 167 innings didn’t even crack the top 10 – for the Cy Young Award.

“He’s been worth every penny,” manager Rob Thomson told reporters last September.

Of course, the man behind the ace’s extension is none other than Dave Dombrowski, Boston’s former president of baseball operations. Since agreeing to take on the same role with the Phillies in December 2020, he’s built the previously-languishing club into a force to be reckoned with.

To do so, he had to convince owner John Middleton to allow him to do something that the Phillies had never done before: exceed the luxury tax. Among Dombrowski’s biggest spends were his re-signing of superstar catcher J.T. Realmuto in January ’21, free-agent contracts to Kyle Schwarber (four years, $79M) and Nick Castellanos (five years, $100M) in March ’22 and Trea Turner (11 years, $300M) and Taijuan Walker (four years, $72M) in December ’22, and an extension for homegrown star Aaron Nola (seven years, $172M) back in November. Now, barely two weeks after declaring a Wheeler extension “a priority for us,” Dombrowski has made it happen.

As with the blockbuster moves Dombrowski made for the Red Sox – including a then-record contract for David Price, the Chris Sale and Craig Kimbrel trades, and signing JD Martinez – the Phillies’ spending sprees began paying dividends almost immediately. A postseason berth was just out of reach in ’21, but they compiled their first winning season since ’11. In ’22, they clinched their first-ever Wild Card berth, ending their National League-leading playoff appearance drought and going from lowly third Wild Card spot to their first pennant since ’09 before losing the World Series to the Houston Astros. They were over the Competitive Balance Threshold again last year, and made the postseason again, but fell to the Arizona Diamondbacks in seven games in the penultimate round. Spotrac currently has them nearly $16 million over this year’s $237 million threshold, as well.

Wheeler has been instrumental to the Phillies’ newfound postseason success. His 2.42 ERA across two Philly postseason runs ranks sixth-best in MLB history (minimum 10 starts). According to Elias Sports, his 0.73 WHIP in his first 10 career postseason starts is not only the lowest mark for any 10-start span in postseason history, but the best career WHIP in postseason history by any pitcher who threw a minimum of 50 postseason innings.

The Red Sox, meanwhile, have eschewed big spending almost entirely since firing Dombrowski in September 2019, opting for almost a full-scale rebuild. Save for Rafael Devers, they’ve parted ways with every member of the ’18 championship team Dombrowski constructed, stripping the payroll and focusing on the farm. They’ve finished last in their division thrice in four seasons, and are projected to three-peat at the bottom of the standings this year. Despite ample space under this year’s luxury tax threshold, no current CBT penalties, and their own publicly-stated roster needs, they’re continuing to operate on a self-imposed budget, earning the ire of their own players, past and present, and executives around the league.

There are no options in Wheeler’s new deal, which keeps him in the City of Brotherly Love through 2027. He’ll also earn 10-and-5 Rights upon completion of the upcoming season; he’s already reached 10 years of Major League service time and with five consecutive seasons with the same team, he’ll be able to veto any trade proposal.

The Wheeler news brightens up an otherwise bittersweet day for Philadelphia sports; after spending his entire 13-year NFL career with the Eagles, Jason Kelce officially announced his retirement on Monday.



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