Major League Baseball’s Winter Meetings certainly will be different this year. Instead of the entire industry swarming the Omni Dallas Hotel, the annual event will occur virtually due to the coronavirus pandemic.

But despite the substantial changes, this week should be an important one for the Pirates.

A year ago, general manager Ben Cherington talked about the Winter Meetings as a time to learn, to hold staff meetings and discuss processes. It was a measured and necessary approach. Given what has transpired since then, it’s reasonable to expect a little more action this time around.

Exactly what should fans expect? Let’s take a look.

Make some trades

It simply wasn’t smart to do this sort of stuff in 2019. Cherington wanted to know more about what he had, and if the 2020 season was any indication, it’s not nearly as much as he’d like. So the time has probably come to mortgage a few arbitration-eligible veterans into younger prospects the Pirates can develop.

The three smartest fits for the Pirates in this particular conversation are Joe Musgrove, Adam Frazier and Richard Rodriguez.

Musgrove, who had a career-low 3.86 ERA in 39 2/3 innings this past season, saw his strikeouts per nine spike to 12.48. His previous best was 8.30 in 2019. For a 28-year-old with strong leadership traits and a projected arbitration figure around $4 million, this one shouldn’t be hard. The only change could be if the Pirates and Musgrove found common ground on a long-term contract extension.

In Frazier’s case, it doesn’t make sense for the Pirates to offer a long-term deal because of the middle-infield prospects they have in their system — Nick Gonzales, Oneil Cruz and Liover Peguero, all in the top five. Cherington could’ve moved Frazier had he wanted to last year. While Frazier endured some offensive struggles (.661 OPS compared to career mark of .749) in 2020, he was also a Gold Glove finalist for a second consecutive year and showed flexibility by occasionally manning left field.

Bottom line, there should be at least two deals for Cherington to make, plus potentially a third with Rodriguez, the Pirates’ wins (3) and saves (4) leader, as well as someone whose WHIP (0.80) was the fifth-lowest among National League relievers with at least 20 innings pitched. Rodriguez also averaged a career-best 13.11 strikeouts per nine.

Learn the landscape

There are two key components to the baseball landscape that everyone probably should’ve learned for sure a long time ago: the identity and structure of all 120 minor-league affiliates, as well as a definitive answer on whether or not the designated hitter will remain in the NL.

According to sources, the expectation is for the Pirates to retain four affiliates: Class AAA Indianapolis, Class AA Altoona, High-A Bradenton and Class A Greensboro. However, nothing has been finalized.

As for the DH, Cherington has maintained that any and all communication he’s received from the league would indicate that the DH is not coming back, though MLB has not told the public anything definitive. The expectation is for both things to be finalized next week amid the (virtual) Winter Meetings.

Add an outfielder

Cherington told the Post-Gazette last week that he expects to address his outfield depth at some point this offseason, though he didn’t specify how he expected that to happen. It’s certainly needed as Cole Tucker — who’s battling to become the starting shortstop — offers the most experience of any potential outfielder aside from Bryan Reynolds, Anthony Alford or Gregory Polanco.

Tucker (247 2/3 ) actually has more MLB innings in the outfield than Alford (214), though Tucker only started playing the position in 2020. So, getting someone with a little more experience is probably prudent.

Who might they sign, you ask?

Coming off a 2.5 fWAR season, Kevin Pillar would be a dream option for many Pirates fans. Cherington knows him extremely well from their time together in Toronto, while Pillar, 32, remains one of the better defensive outfielders in baseball. He also produced a career-high .798 OPS in 2020.

After completing a one-year deal for a non-pro-rated $4.25 million, it’s hard to see Pillar taking a pay cut. It’s also hard seeing the Pirates spend perhaps three times as much as they gave Jarrod Dyson in 2019 when they’re coming off a 19-41 season.

Assuming Pillar doesn’t work out, there are several options that better fit within the Pirates’ price range. Delino DeShields, Tyler Naquin and Ben Gamel are all between 28 and 30 and produced between .7 and 1.1 fWAR in 2020. They have experience in center field, too.

A really intriguing option might be former Rockie David Dahl. Colorado non-tendered its 2012 first-round pick after he hit just .183 in 24 games and battled a shoulder injury. But from 2016-19, Dahl put up some really good numbers: a .297/.346/.521 slash line, as well as an average of 38 home runs, 133 RBIs, 140 runs, 51 doubles and 12 triples in 240 games.

The market will obviously matter, but it could be a chance for the Pirates to buy low on a talented young player.

Finish strong

The Winter Meetings always conclude with the Rule 5 draft. Last year, the Pirates chose not to pick anyone, although that’s unlikely to repeat considering Pittsburgh holds the No. 1 overall pick.

And again unlike 2019, there are some intriguing prospects for the Pirates to potentially add.

—Garrett Whitlock is a hard-throwing righty in the Yankees system. MLB Pipeline current ranks him No. 19, and he’s coming off Tommy John surgery. But he’s got an excellent sinker-slider combo — something pitching coach Oscar Marin seems to like — and he’s been developed as a starter, meaning they could stash him in the bullpen and have him pitch lower-leverage innings to get comfortable.

—Catching prospects will remain a conversation topic until the Pirates have a few. Two of the more intriguing options: Julio E. Rodriguez (Cardinals No. 15) and Payton Henry (Brewers No. 15). Henry had 14 homers and 75 RBIs at High-A in 2019, while Rodriguez — who reached Class AA in 2019 — is considered an above-average defender. The issue would be keeping either on the roster when the Pirates are seemingly set with Jacob Stallings and Michael Perez.

—Here’s who might make the most sense: Buddy Reed, an athletic outfielder from the … well, Athletics. Reed is a switch-hitter and former two-sport athlete, similar to Alford. His scout grades (20-80 scale) are 60 for his arm, 65 for his fielding and 70 for his speed. Reed stole 51 bases in 2018 split between two levels. He had 14 homers and 50 RBIs in 2019 at Class AA. The issue? He hit just .228 and struck out way too much (126 in 423 plate appearances or roughly 30% of the time). But if you let Reed get comfortable by emphasizing defense and live with the offense as a work in progress, there may be a dangerous player under there.

—Will Benson, an outfielder in the Indians system, could garner a second look. He was the 14th overall pick in 2016 and led the Midwest League with 22 homers in 2018. But like many, he hasn’t made enough consistent contact (31% strikeout rate, .212 average) in the minor leagues.

— Alex Speas is a hard-throwing righty in the Rangers system, a pitcher Marin should know well from his days there. Speas has topped out at 102 mph, but he often doesn’t know where the heck it’s going (6.9 walks per nine).

— The last name to know is Jose Alberto Rivera, a righty in the Astros system. He’s actually considered Houston’s 14th-best prospect by MLB Pipeline and was scouted by Pirates special assistant Oz Ocampo, meaning there’s some intel there. Rivera has seen his velocity climb a good 5 mph over the past two-plus years while striking out 95 in 75 2/3 innings at Class A in 2019.