The top 10 moments of McCutchen's career

When the Pirates selected Andrew McCutchen in the 2005 Draft, they knew the outfielder had five strong tools and they hoped it would translate to the Majors. How that worked out: Five All-Star nominations, four Silver Sluggers, a Gold Glove Award and ... well, let's save the biggest accolade for the list below.

Though McCutchen left Pittsburgh in 2018 when the club traded him to the Giants, he always come back to a standing ovation at PNC Park no matter which uniform wore as a visitor. And why wouldn't he after what he did to revitalize the club after a long stretch of losing seasons?

And now, he'll be back as a member of the home team. McCutchen and the Pirates agreed to a one-year contract on Friday, per a source, meaning that he will have a chance to submit some new entries for this list in 2023, all while wearing the black and yellow.

Most of the top moments of McCutchen's career have come with the Bucs, but a few have come with other clubs. A few of the moments on this list are meant to illustrate the many facets of his game and personality beyond the incredible offense he produces. Here is a look at 10 of the best moments from McCutchen's career.

1. Best of the best
Nov. 14, 2013

Entering 2013, the Pirates had not had a player win the NL MVP Award since 1992, when Barry Bonds claimed his second for the Bucs. It was the longest drought for Pittsburgh without an MVP Award since 1960, when Dick Groat broke a 33-year skid.

The droughts also correlated to a long Pirates postseason drought. When McCutchen won the 2013 NL MVP Award, garnering 28 of the 30 first-place votes, he cemented himself as the prime figure in a three-year run of postseason appearances and pivoted from being simply a face of the franchise into a face of the franchise’s success.

2. A reason to root
Aug. 25, 2009

The 2009 Pittsburgh Pirates team was one of the worst so far in the 21st century on paper, with the fifth-worst winning percentage of any team from 2000-21 (.385). But in retrospect, those struggles were a little less heavy to carry for a fanbase as a star came into being.

McCutchen debuted in 2009, and it would have been easy to pick his first hit or his first home run as a top moment of his career. Maybe the bigger moment from that season was his first walk-off homer on this date.

Pirates closer Matt Capps blew a save attempt in the top of the ninth, giving the Phils a 4-3 lead. That kind of blow usually crushed a team like the Pirates, who had the third-lowest OPS in the Majors that year. But after Brandon Moss knocked an RBI single against a struggling Brad Lidge, Cutch hit a deep drive to center to win it and jumped into the home-plate festivities at full speed. Here was a reason to cheer.

3. Among the greats
Sept. 13, 2017

As of the end of 2022 season, McCutchen ranked tied for 171st all time in home runs with 287. Of that total, 203 came in Pittsburgh.

McCutchen crossed the 200-homer threshold on this date at Milwaukee’s then-named Miller Park, making him the fourth Pirate in franchise history to hit 200 home runs with the club. Ahead of him on the franchise leaderboard are some legendary names: Willie Stargell (475), Ralph Kiner (301) and Roberto Clemente (240). Now McCutchen will have the chance to hit No. 300 as a Pirate, if he can go deep at least 13 times in 2023.

4. Outta here!
April 7, 2018

McCutchen did not have the strongest first week with the Giants after his trade in 2018, going 2-for-24 in his first six games. But those in attendance at Oracle Park (called AT&T Park at the time) for the season’s first rivalry game with the Dodgers would trade those struggles for a night like April 7, 2018, every single time.

Over his first four at-bats, McCutchen notched four hits, drove in a run and scored once. However, with the winning run at second base and two outs in the ninth inning, McCutchen grounded out to send the game to extra innings.

McCutchen was determined not to let that happen again when it came down to him once again in the 14th inning, as he sought his sixth hit. He worked a 12-pitch at-bat against Wilmer Font, then got a fastball that wasn’t elevated and sent it to left field for a walk-off three-run homer with one of his most iconic celebrations to date.

"It's one of those Giants-Dodgers games that will be talked about,” former Giants manager Bruce Bochy said.

5. Leaving a lasting impression
Sept. 26, 2017

When the Pirates played the Orioles at PNC Park in late September of 2017, fans didn’t know it would be their last chance -- at least for a while -- to see a franchise great take the home field in a Bucs uniform. On Jan. 15 in the following offseason, McCutchen was dealt to the Giants for Bryan Reynolds and Kyle Crick.

In that two-game set against the O’s, McCutchen decided to open it with a show. He opened the scoring with an RBI double in the first inning, then hit a grand slam in the second inning. O’s starter Kevin Gausman began to settle in a bit more after that, not allowing another hit until McCutchen led off the fifth with a single before he scored on a groundout.

McCutchen was a triple shy of the cycle, yet in his final at-bat of the day in the sixth inning, he swung for the fences once again to hit a three-run blast over the Clemente Wall. In what was effectively his send-off from PNC Park, he notched a career-high eight RBIs and gave the fans a memory to cherish.

6. 'Oh my God!'
July 11, 2015

The Pirates’ game against the Cardinals on this date may have been one of the weirdest set of circumstances McCutchen found himself the hero in.

By the second inning, Bucs manager Clint Hurdle and catcher Francisco Cervelli had been ejected for arguing a foul-tip call. St. Louis scored its second run in the fifth on a botched fielding attempt. The Pirates finally scratched a run across thanks to a home run from starting pitcher A.J. Burnett, which marked his first in a decade.

Somehow, the Pirates got the game to extra innings and stretched the bout to the 14th inning. With the team down by a run, McCutchen launched a two-run walk-off homer that sent PNC Park and Pittsburgh’s TV booth into a frenzy for one of the most iconic calls of McCutchen’s tenure with the Pirates.

7. A pair of gloves
May 31, 2015

Outside of McCutchen’s excellence on the baseball field, it’s important to note what makes him one of today’s game’s “good guys.”

McCutchen was known in the dugout as someone ready to bust a move at any time and celebrate the small things. He’d been hit by 77 pitches through 2021, yet he’s never been one to charge the mound. He makes jokes and shares smiles on his social media platforms, which are relatively active compared to others in the league.

Marry that spirit with the faith he inspires through his play, and you get a moment like that on May 31 at Petco Park. McCutchen sees two young Pirates fans celebrating in the outfield seats, so he trots over, hands them his batting gloves and shakes hands with them before heading to the clubhouse. You can see the boy yelling a popular sentiment among the Bucs’ faithful fans: “I love you, man! I love you!”

8. Making it look easy
May 22, 2014

McCutchen is not one of the statistically great defensive outfielders of this generation, but in Pittsburgh, he made a bunch of standout plays in center field. Perhaps none were better than his win-sealing snag against the Nationals on this date.

With the go-ahead run at the plate and two outs, Pirates closer Mark Melancon allowed Anthony Rendon to hit a well-struck liner to center field, short of where McCutchen was positioned. Sprinting diagonally to his right with little time to spare, he readjusted his body as he was low to the ground and tucked his glove into his left side to make it look much easier than it was.

Even Josh Harrison had to bow down for the effort, which sealed the second win in a stretch of victories that put the Pirates back on track to reach the postseason again.

9. Run, run, run
Sept. 10, 2014

McCutchen hasn’t stolen more than 15 bases in a season since 2014, but coming up, he was one of the speediest prospects in the Pirates’ system. He averaged nearly 24 stolen bases a season from ‘09-14, but his speed played out in other ways, too.

A key example came on this date, when the Pirates faced the Phillies at Citizens Bank Park. McCutchen hit a long fly ball off the wall in left-center field, which ricocheted past the leaping outfielder Ben Revere toward right field. Cutch made the effort look breezy, standing up as he touched home plate for an inside-the-park homer that tied the game.

10. Ring my bell
July 26, 2021

McCutchen spent 2019-21 on the other side of the state from his first team, the Pirates, as the Phillies offered him a three-year, $50 million contract in the ‘18-19 offseason -- the same winter Bryce Harper signed his mega-contract with the club.

Though his production on offense dipped a bit compared to his glory years with the Pirates, McCutchen, ever the entertainer, still produced memorable moments in Philadelphia. The most exciting came on this date, when the Phillies found themselves down two runs in the bottom of the ninth facing closer Brad Hand, who led the Majors in saves in 2020. But with runners on the corners, Cutch swung on the first pitch and clocked a home run into the right-field seats to win the game.