The MLB Winter Meetings kicked off on Sunday, and will last until Wednesday December 7. There is already plenty going on, with the potential of even more excitement throughout the week.

With all of the GMs packed into one hotel, along with agents, there are several big name free agents that have yet to sign that we could see deals made for. There are also several trade rumors going on right now, including one with a familiar name.

Here are a few things that we know are going to happen this week, along with a few potential highlights.

– Major League Baseball will host its first ever lottery to determine the draft position on Tuesday. The Pirates will have a 16.5% chance of getting the first overall pick, tied with the Washington Nationals and Oakland Athletics for the highest odds.

Of course when it comes to draft position, maybe the exact position isn’t as important but it does have big implications on the bonus pool, and we saw what the Pirates did in 2021 with the top pick.

Ethan Hullihen recently did a full breakdown of the draft lottery system, as well as the Pirates’ full odds.

– Wednesday will bring the Rule 5 draft at 5 PM EST, which we’ve had plenty of coverage here leading up to it. The Pirates cleared up a couple of roster spots going into the weekend, which opens up the possibility of them selecting a player. 

While there is a lot of Rule 5 build up over the concern of losing a prospect, a lot of times the entire event falls flat. The odds that a player sticking with the organization that drafted them is very rare, and even if they do, the impact is generally minimal.

– The biggest thing that will be of note is any ground that is made, or any foundation set on a potential Bryan Reynolds trade. The outfielder requested a trade this weekend, and things seem dire in any hopes to change his mind. There are already teams who have expressed interest.

That being said, the Pirates don’t have to trade him. He’s already under contract for the upcoming season, and will be under team control beyond that. This would of course be a perfect time to get some feelers about what his current value is, however, and a potential trade of Sean Murphy could also give the Pirates an idea.

Update on Sean Murphy: it still appears Oakland is close to a trade, but the Braves are NOT going to be the acquiring team, per source. The Cardinals, Rays, Guardians and Red Sox are among the teams that have been connected to Murphy in recent weeks.

— Mark Feinsand (@Feinsand) December 4, 2022

If the Pirates are going to trade Reynolds, they are already going to catch some bad backlash for it, so holding out to make sure they get their absolute best return would be the ideal route to take.

– Ben Cherington could also look to make another trade, or even sign a free agent. Catcher, starting pitcher, and (depending on Reynolds) outfielder could be targets for the Pirates.

Highlight of the Day

Pirates Prospects Daily

By Tim Williams

**There is going to be a lot of talk about Bryan Reynolds this week, and I rounded up the early rumors surrounding the All-Star outfielder. Right now he’s drawn interest from the Yankees, Rockies, and Braves.

**One of the highest traffic articles this time of year is anything with the phrase “Rule 5”. Ethan Hullihen looked at who the Pirates selected and lost over the last decade, and if you didn’t notice the trend, it shows that while the Rule 5 draft is fun and interesting, it is far from significant. I’ll have a column on this phenomena on Wednesday.

**John Dreker has the latest Pirates winter league updates, where 16 Pirates saw action. If you missed it, check out his latest Pirates Winter Report on Rodolfo Castro.

**Missed yesterday? Anthony wrote about the Bryan Reynolds trade rumors, and how the split between him and the Pirates might be inevitable.

Song of the Day

Pirates Prospects Weekly

Ethan Hullihen broke down the history of the Pirates’ Rule 5 picks — selected and lost — over the last ten years. I’ll have some additional thoughts on the draft this week.

Pirates Business: A History of Pittsburgh Pirates Rule 5 Selections

I’ll have First Pitch at noon on Monday, giving my thoughts on the Pirates outlook heading into the meetings.