Set to retire at end of 2016 season, relive David Ortiz’s biggest playoff hits

With David Ortiz set to retire at the end of the 2016 season, Cliff Corcoran looks back at the Red Sox legend's five biggest postseason hits.

David Ortiz will turn 40 years old on Wednesday, and, according to a tweet from FOX Sports’ Ken Rosenthal on Tuesday, has decided that 2016 will be his final year as an active major-league player. Ortiz has an option on his contract for 2017 that could vest at anywhere from $10 million to $16 million (value based on plate appearances in the coming season) if he were to pass a team physical at the end of the ’16 season, but if he intends to retire, he will likely never take that physical, leaving as much as $16 million on the table.

UPDATE: Ortiz has made it official, announcing his post-2016 retirement in a video for Derek Jeter's website, The Players' Tribune.

Heading into his age-40 season, Ortiz has no more accomplishments to chase. He holds most of the major cumulative records for designated hitters, including most hits (2,023), home runs (447), doubles (509), total bases (3,907), RBIs (1,443), runs scored (1,175), walks (1,091), games played (1,887) and plate appearances (8,248) at the position. He hit his 500th home run on Sept. 12, finishing the season with 503 career round-trippers. Perhaps most significantly, at least in terms of how he will be remembered, Ortiz won three World Series with the Red Sox, a team that had gone 86 years without a championship before his arrival in Boston but has won three times in his 13 years with the team.

Ortiz was a central part of all three of those championship teams and an elite performer in all three of those postseasons. Indeed, even more than his status as one of the two greatest designated hitters of all time (requisite hat-tip to Edgar Martinez), Ortiz will be remembered for his postseason heroics. With that in mind, on the occasion of Tuesday’s news about his impending retirement, here’s my attempt to rank the five biggest hits of Ortiz’s fantastic, Hall of Fame-worthy, career.

1. 2004 ALCS Game 4 walk-off home run

Ortiz holds the all-time record for most postseason walk-off hits with three and is tied with Bernie Williams for most postseason walk-off home runs with two, and all of those hits came in the 2004 postseason as the Red Sox clawed and scratched their way to their first championship in 86 years. This was the most important and remains the most famous of the three. Though Game 4 of the 2004 ALCS is more famous for Dave Roberts’s stolen base and subsequent game-tying run against Mariano Rivera in the bottom of the ninth inning, the Red Sox—who entered that game trailing 0–3 in the best-of-seven ALCS and entered the bottom of the ninth trailing 4–3—didn’t fully avoid elimination in that inning. Despite Bill Mueller reaching third base with just one out in that inning, Rivera managed to keep the game tied, and the Red Sox and Yankees played three more innings, any one of which could have seen New York complete its sweep of the series.

Then came the bottom of the 12th. With the game still tied 4–4 and Paul Quantrill on the mound in relief of Tom Gordon, Manny Ramirez led off with a single, bringing up Ortiz, who had walked and singled in five previous plate appearances in the game. Quantrill fell behind Ortiz 2–1, then hung a slider on the inside half of the plate; Ortiz hit it into the visiting bullpen over the 380-foot sign in rightfield to give the Red Sox the first win in what would prove to be the most dramatic series comeback in major league history.

2. 2004 ALCS Game 5 walk-off single

The very next night, the Red Sox were again fighting to stay alive in extra innings in a 4–4 game that stretched beyond five hours in length following a blown save by the Yankees. In this game, Ortiz had an RBI single in the first and a solo home run in the bottom of the eighth, the latter bringing Boston to within one run of New York, setting up the game-tying rally later that inning. Ortiz had already struck out, walked and been inexplicably caught stealing in extra innings by the time his place in the order came back around in the bottom of the 14th inning. As was the case the previous night, Ramirez was on first base, but this time there were two outs and Johnny Damon was on second; he and Ramirez had both drawn walks against the Yankees’ Esteban Loaiza, who was by this time in his third inning of work.

Loaiza got within one strike of getting out of the jam. However, on a 2–2 pitch—a curveball up and in that appeared to jam Ortiz—the DH flared a broken-bat single into center that brought Damon home with the winning run. That hit ended a five-hour, 49-minute marathon, gave the Red Sox their second win of the series and sent the ALCS back to New York, where Boston would complete its unprecedented comeback on its way to that curse-busting championship.

3. 2003 ALDS Game 4 series-saving double

The 2003 season, Ortiz’s first with the Red Sox, was his coming-out as a star player in the major leagues, and this hit was the first series-altering postseason hit of his career. It came in the bottom of the eighth inning of Game 4 of the division series against the Athletics, Boston’s first postseason series in four years. The A’s had won the first two games of the series in Oakland, and though the Red Sox had won Game 3 on Trot Nixon’s walk-off home run, Boston was losing Game 4, 4–3, in the bottom of the eighth. The Red Sox were four outs away from elimination when Ortiz came to the plate to face A’s closer Keith Foulke, who would record the final out of Boston’s World Series win a year later.

Nomar Garciaparra was on third base via a double and Ramirez’s subsequent single, putting the tying and go-ahead runners on the corners for Ortiz with two outs. Ortiz worked the count full, then crushed a fastball over rightfielder Jermaine Dye’s head to the warning track. The ball ricocheted off the short wall in Fenway Park’s rightfield back past Dye, allowing both runners to score and giving Boston a 5–4 lead. Scott Williamson retired the side in the top of the ninth to nail down that series-tying win, and the Red Sox won Game 5 in Oakland the next day to clinch the series and advance to their memorable ALCS confrontation with the Yankees. By Win Probability Added, that double was the biggest postseason hit of Ortiz’s career, as it improved Boston’s chance of winning this game by 52%.

4. 2013 ALCS Game 2 grand slam

The Tigers won Game 1 of the 2013 ALCS 1–0, then held a 5–1 lead in the eighth inning of Game 2. Will Middlebrooks hit a one-out double in the eighth and Jacoby Ellsbury followed that with a walk, but when Al Alburquerque struck out Shane Victorino for the second out of the inning, those two base runners seemed incidental. Then Dustin Pedroia singled off Alburquerque to load the bases and bring up Ortiz. Tigers manager Jim Leyland countered not with lefty specialist Phil Coke, but with righthanded setup man Joaquin Benoit. Benoit, whose best pitch is a splitter, started Ortiz off with an 86-mph splitter away, and Ortiz, who said after the game that he knew he wasn’t going to get a fastball in that situation, was ready for it. Ortiz deposited the pitch in the Boston bullpen—just beyond the reach of Torii Hunter, who toppled over that short rightfield wall, and past a celebrating police officer—for a game-tying grand slam. The Red Sox won the game on Jarrod Saltalamacchia’s walk-off single in the next inning and won the series in six games on their way to yet another championship.

Ortiz’s grand slam remains one of just three game-tying grand slams in postseason history, joining Ron Cey’s seventh-inning shot off Steve Carlton in the 1977 NLCS and Vladimir Guerrero’s seventh-inning shot off Mike Timlin in Game 3 of the 2004 ALDS between the Angels and Red Sox. The latter was rendered insignificant by yet another clutch postseason home run from Ortiz, one which just happens to be the next hit on this list.

5. 2004 ALDS Game 3 series-clinching walk-off homer

Unlike the first four hits on this list, the Red Sox were not in danger of being eliminated or falling into a deep hole in this series had Ortiz not come to the rescue. Boston had won the first two games of this division series in Anaheim and had a 6–1 lead in this game before the Angels rallied in the seventh, tying the game on Guerrero’s two-out grand slam. The 6–6 tie lasted into the bottom of the 10th inning, when Damon led off with a single and moved to second on a sacrifice bunt by Mark Bellhorn. Francisco Rodriguez, who was still setting up closer Troy Percival that season, struck out Ramirez for the second out of the inning, but with Rodriguez having thrown 38 pitches and the lefty Ortiz due up with the series-winning run in scoring position and two outs, Angels manager Mike Scioscia brought in lefty starter Jarrod Washburn to pitch to Ortiz. Washburn hadn’t made a relief appearances in five years, and this one lasted all of one pitch, a curveball that Ortiz deposited in the Green Monster seats above Fenway Park’s 37-foot-high leftfield wall to send the Red Sox to the ALCS.

Ortiz’s home run is one of just nine series-ending home runs in postseason history, joining famous shots by Bill Mazeroski, Chris Chambliss, Joe Carter, Todd Pratt, Aaron Boone, Chris Burke, Magglio Ordoñez and, most recently, Travis Ishikawa.

Bonus: Ortiz’s biggest regular-season hit

Ortiz has hit 11 walk-off home runs during the regular season. Twice in his career—twice in the 2006 season, to be exact—Ortiz came to the plate with the Red Sox trailing by two runs with two men on and hit a three-run walk-off home run. The second of those came with one out against Indians closer Roberto Hernandez on July 31 of that year. The first came against Rangers closer Akinori Otsuka with two outs and two strikes on June 11 and stands as the biggest hit, by WPA, of his entire career. With one swing, Ortiz took the Red Sox from a mere 10.1% chance of winning to a victory.