Jon Lester

What if A's hadn't traded Yoenis Cespedes for Jon Lester back in 2014?

What if A's hadn't traded Yoenis Cespedes for Jon Lester back in 2014?

Editor's note: Twice a week, NBC Sports Bay Area will look back on biggest "What If?" moments in Bay Area sports history in our "Hindsight 2020" series. The second installment: What if the A's hadn't traded Yoenis Cespedes for Jon Lester in 2014?

Billy Beane added to the A’s starting rotation in 2014 with a massive midsummer trade, acquiring pitcher Jeff Samardzija on July 5 to strengthen a roster already performing better than any in major league baseball.

The A’s reversed field somewhat and became buyers in the trade market, a surefire sign they were going for it. Their offense could rake and a solid staff that got a lot better with a major transaction. That blockbuster seemed to be the A’s move.

But that’s why everyone was so shocked by what happened the day of the trade deadline.

Beane, then the A's general manager (he's since been promoted to VP of baseball operations), shipped star outfielder Yoenis Cespedes and a competitive balance pick to the Boston Red Sox for Jon Lester, Jonny Gomes and cash. It was a move that, even in today’s modern media landscape where nothing stays secret for long, was considered a legitimate shock.

“They made the Samardzija trade before that, and that was big deal for a starter who could help down the stretch,” A’s play-by-play broadcaster Glen Kuiper said in an interview with NBC Sports California’s Brodie Brazil. “They made a big trade and that seemed like the one even though it came in early July. You just weren’t expecting another trade, especially another trade for a starting pitcher. That’s another reason why it surprised people.”

Lester gave the A’s a bonafide ace in the prime of his career -- though clearly a rental -- and cost a star outfielder in the prime of his career with another year remaining on his contract.

“My mind is blown,” then-A’s outfielder Josh Reddick told the San Francisco Chronicle right after the trade. “I’m still trying to wrap my mind around this. Never in my wildest dreams did I think we would give up ‘Cespy.’ But it makes sense in the long run to get another guy who is an ace.”

The A’s led the league in runs scored at the time. Beane built up the rotation during the season to include Lester, Sonny Gray, Scott Kazmir, Samardzija and Hammel. They already had Sean Doolittle in the closer’s role and seemed primed to finish the 2014 campaign as well as they started it.

They also acquired outfielder Sam Fuld back from the Minnesota Twins for Tommy Millone, reinforcing the outfield along with Gomes.

The adjusted roster did not produce great results. They had baseball’s best record on July 31 but floundered through a 12-17 record in August and a 10-13 September. The Los Angeles Angels surged in the opposite direction following an excellent July, with a 34-21 record the last two months.

That left the A’s clinging to a wild card spot and a one-game playoff. Lester was on the mound for the game he was acquired to pitch, but the A’s fell short, collapsing in the late innings as the Kansas City Royals stormed back and won in walk-off fashion in the 12th inning.

The season’s disappointing end put the A’s moves, the Cespedes trade in particular, in a negative light through hindsight.

Beane made one point clear to reporters after the A’s season ended: His team wouldn’t have made the playoffs without Lester. He’s probably right, considering Lester had a 2.35 ERA and the lowest WHIP of his career (1.07), over 76.2 innings in 11 starts. He even took a lead into the eighth inning of the wild-card game before it slipped away.

The trade’s detractors will point to the fact the A’s offense fell apart in mid-August and never got its groove back, but it’s hard to certainly say the Green and Gold made a misstep -- especially when viewed in context.

"The Angels were going to catch us," Beane told reporters after the season, via ESPN. "They played nearly .700 ball from a certain point. If you go back to my quotes from when we made those trades, despite the fact of where we were, at no point were those trades made for the playoffs. I was adamant about it. I could feel the Angels breathing down our necks.

"What I didn't reveal was that I was also concerned about us, which was the point of the trades. I have said this many times: It's not where you are, it's where you're headed. And I like to think being here every day, I have a feel for where we're headed."

If we’re going to project what might’ve happened if Beane didn’t trade Cespedes for Lester, maybe the GM is right. Maybe the A’s falter down the stretch and don’t reach the postseason.

Or ... maybe the keep their high-octane offense going down the stretch. There was no doubt the A's missed Cespedes after he was gone, on the field and in the clubhouse. He was a true cleanup hitter who made everyone around him better.

“I’ll never forget talking about him with Bob Melvin later, maybe a couple of years ago. Cespedes didn’t speak much of any English, but Bob said he was a leader,” Kuiper said. “He was a leader because he wanted the spotlight on himself. He wanted it. When you have a guy who is great and wants to be in the spotlight, it takes a lot of pressure off the guys around him. In that case it was (Brandon) Moss and (Josh) Donaldson and (Josh) Reddick.

"He had no problem taking it on and living in the spotlight. When he went out of the mix in trade, the spotlight shifted to those other guys. Then it was up to them to handle it. This is an in-depth, clubhouse way to look at it but, if you think about it, it makes a lot of sense.”

Losing a fan favorite and a productive player never goes over well with the fanbase, especially considering the trade’s surprise element and the fact that the slugger had another year left under his contract.

Cespedes bounced around after the A’s trade. Boston shipped him to Detroit after the 2014 season, and then the Tigers moved him to the New York Mets at the 2015 trade deadline.

[RELATED: Hindsight 2020 - What if Warriors had traded Klay for Love?]

It’s impossible to imagine the A’s would’ve inked him to a three-year, $75 million deal the New York club gave him before the 2016 season, a contract that included an opt-out clause after that campaign he exercised. Cespedes signed a four-year, $110 million contract with the Mets that he has been injured throughout. The A’s would have lost him to free agency or a trade with far less return than Lester.

The left-hander was a rental from the start, eventually leaving for the Chicago Cubs after the season on a massive, $155 million deal. Gomes didn’t stick around after the season, so no team came out ahead in the long run.

There’s disappointment in the 2014 season’s final results, but it’s clear what the A’s were trying to do by reaching the postseason with the pitching required to take them on a run.

“I will say, though, that the A’s had a plan,” Kuiper said. “We knew we’re good enough to get into the postseason and we needed an ace, a No. 1 guy. As it worked out, they had Lester for the wild card game. It didn’t work out as they had hoped, but if you look at the A’s plan, it all lined up for Lester.

"He pitched in the wild card game and threw pretty well up until late in the game. It got one inning away from working, but Lester ran out of gas a little bit.”

Why Giants' Madison Bumgarner is 'most fascinating' in MLB free agency

Why Giants' Madison Bumgarner is 'most fascinating' in MLB free agency

The Giants will try to re-sign Madison Bumgarner if they can, but it's going to be costly.

While the three-time World Series champion isn't the same pitcher he used to be, Bumgarner will have no shortage of suitors on a free-agent market that includes some high-profile names.

And while Gerrit Cole, Anthony Rendon and Stephen Strasburg are stealing the headlines and expected to receive the largest paydays, Bumgarner exists as the "most fascinating" free agent outside of those three, according to ESPN's Jeff Passan.

"Madison Bumgarner has been so good for so long, it's easy to lose appreciation of what he has been and what he might become," Passan wrote. "In a lot of ways, Bumgarner's career numbers mirror those of another left-hander who signed a long-term deal before his age-30 season: Jon Lester. 

"Bumgarner comes with more mileage than Lester and didn't have nearly the same walk season, but the stuff itself is very similar. Lester's fastball velocity going into free agency: 91.8 mph. Bumgarner's last season: 91.4 mph. Lester's cutter: 87.8 mph. Bumgarner's slider: 87.3 mph. Both throw a looping curveball and a changeup too."

Lester signed a six-year, $155 million contract with the Cubs after the 2014 season. While Passan doesn't necessarily expect Bumgarner to receive an identical offer, he rejects the notion that MadBum has precipitously fallen off.

"The idea that Bumgarner is some diminished version of himself is ludicrous," Passan continued. "His 207 2/3 innings last season illustrate that, as do his 203 strikeouts and nearly 5-to-1 walk rate. All that from the best pitcher in World Series history? That should play."

[RELATED: What Giants giving qualifying offers to MadBum, Smith mean]

MLB Trade Rumors predicts Bumgarner will sign for substantially less than Lester did. However, it only takes one team, and that still could be San Francisco.

A's vs. Cubs lineups: Khris Davis out again as Jon Lester takes the mound

A's vs. Cubs lineups: Khris Davis out again as Jon Lester takes the mound

The A's will try to even their interleague series with the Cubs on Tuesday night at Wrigley Field in Chicago.

With no designated hitter in the National League ballpark, Khris Davis will once again sit out, though he will be available to pinch-hit, as he did Monday night when he drew a walk. Chad Pinder will start at second base in place of Jurickson Profar and bat fifth in the order.

Dustin Garneau will be behind the plate and hit eighth. The veteran catcher went 2-for-3 with a double and two RBI in his first game back with the A's on Sunday.

It will be a battle of southpaws on the mound as Brett Anderson takes on Jon Lester. Anderson, 31, enters with a 9-7 record and 4.04 ERA in 22 starts this season. He has a 1.80 ERA in two career starts against the Cubs.

[RELATED: Watch A's Nick Martini's family go wild after homer vs. hometown Cubs]

Lester, 35, is also 9-7 this year with a 3.86 ERA in 21 starts. He is 6-4 with a 3.56 ERA in 15 career starts against the A's. Of course, Lester made 11 starts for Oakland back in 2014, going 6-4 with a 2.35 ERA.

Here are the full lineups for the A's-Cubs game, which will be broadcast on NBC Sports California and the MyTeams app. Coverage begins at 4:30 p.m. PT, with first pitch at 5:05.

Oakland A's (64-49)
Marcus Semien, SS
Matt Chapman, 3B
Matt Olson, 1B
Mark Canha, CF
Chad Pinder, 2B
Stephen Piscotty, RF
Robbie Grossman, LF 
Dustin Garneau, C
Brett Anderson, LHP (9-7, 4.04 ERA)

Chicago Cubs (61-51)
Jason Heyward, RF
Nicholas Castellanos, LF
Kris Bryant, 3B
Anthony Rizzo, 1B
Javy Báez, SS
Albert Almora Jr., CF
David Bote, 2B
Victor Caratini, C
Jon Lester, LHP (9-7, 3.86 ERA)