Mark Feinsand is one of the top MLB insiders when it comes to covering free agents during the offseason, and Alex Bregman has been a recent focus in his reporting. In his latest piece, Feinsand explains how what happens with Bregman could directly impact <a href="https://bolavip.com/en/topic/bo-bichette">Bo Bichette</a>’s future and his potential return to the Toronto Blue Jays.



Feinsand was clear in his MLB.com article titled “Where things stand with top 6 free agents,” highlighting a key factor for Toronto and the infielder’s outlook: “Bichette’s future may be tied directly to what happens with <a href="https://bolavip.com/en/topic/alex-bregman">Bregman</a>, as the Blue Jays and Red Sox are in on both players.”



Feinsand also pointed out that the <a href="https://bolavip.com/en/topic/toronto-blue-jays">Blue Jays</a> hold a notable advantage in Bichette’s case, as they would not be required to give up as much in the process: “Toronto, the only club that won’t have to give up Draft picks to sign Bichette, could bring him back to play second base, where he appeared during the World Series, shifting Andrés Giménez to shortstop.”



<h2>Blue Jays aggressively pursuing Bregman</h2>



As Feinsand outlines in his article, Bichette’s future may hinge on where Bregman ultimately signs. If Bregman were to land with the Blue Jays, it could significantly reduce the chances of Bichette returning to Toronto, even though the club has been one of the teams showing the strongest interest in Bregman.



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“Sources believe the Blue Jays and Diamondbacks may be the two most aggressive clubs in the hunt for Bregman, though a Red Sox reunion remains a possibility,” Feinsand wrote in the section focused on Bregman. In that same analysis, he placed Bichette’s market value ahead of players such as Ketel Marte and Eugenio Suárez.



In a separate, earlier report, Jon Heyman noted that <a href="https://bolavip.com/en/mlb/ny-yankees-rumors-team-reportedly-checks-in-on-blue-jays-star-following-imais-decision">three other teams outside of Toronto and Arizona have also “checked in” on Bichette</a>, a development that could raise some concern within the Blue Jays’ front office.

Mark Feinsand explains how Alex Bregman could shape Bo Bichette’s future with the Blue Jays

Mark Feinsand explains how Alex Bregman could shape Bo Bichette’s future with the Blue Jays - Bolavip US

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The <a href="https://bolavip.com/en/topic/toronto-blue-jays">Toronto Blue Jays</a> have added another arm to their pitching staff, though this latest addition is unlikely to see game action in 2026. The move underscores the team’s ongoing roster reshaping as it reportedly pursues key players like Bo Bichette and <a href="https://bolavip.com/en/topic/kyle-tucker">Kyle Tucker</a>.



Josh Winckowski, 27, spent the majority of his career with the <a href="https://bolavip.com/en/topic/boston-red-sox">Boston Red Sox</a>, but missed significant time this year due to an elbow strain that required surgery earlier this month. His new agreement with the Blue Jays was reported by Steve Adams of MLB Trade Rumors, though the team has yet to announce it.



“Source: Right-hander Josh Winckowski is signing a two-year minor league deal with the #BlueJays. Had internal brace surgery earlier this month. Hoping to pitch late in 2026. Plan right now is to build him back up as a starter when he’s healthy,” Adams wrote.



<h2>Winckowski’s career path and background</h2>



Winckowski’s connection to the Blue Jays dates back to 2016, when Toronto originally drafted him out of high school. After a series of trades, he eventually landed with Boston, where he made his major league debut in 2022 as a starter. That season, he posted a 5-7 record with a 5.89 ERA and 44 strikeouts over 70 innings.



<figure class="wp-block-image size-full"><figure class="image"><img loading="lazy" width="1920" height="1080" src="https://ds-images.bolavip.com/news/image?src=https://images.bolavip.com/webp/en/full/BUS_20260101_BUS_554606_Winckowski_79ae3931.webp&amp;width=1920&amp;height=1080" alt="" class="wp-image-554611"></figure><figcaption>Josh Winckowski #25 with the Red Sox pitches the ball. Abigail Dean/Getty Images</figcaption></figure>



In 2023, he transitioned effectively to the bullpen, emerging as one of the Red Sox’s most reliable relievers. He appeared in 60 games, recording a 2.88 ERA and 82 strikeouts across 88 innings. Despite a promising start to 2025, his season ended prematurely due to the elbow injury that now requires rehabilitation.


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<h2>Outlook with the Blue Jays</h2>



The two-year minor league deal gives Winckowski the time to properly recover without immediate pressure to contribute at the big-league level. The move also reunites him with the franchise that first drafted him, offering a fresh start with a club focused on strengthening its roster for both the present and future. 


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The Blue Jays’ front office will likely monitor his recovery closely while continuing their aggressive offseason pursuits, including efforts to retain Bichette and potentially add impact players like Tucker.

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Blue Jays add former Red Sox pitcher recovering from injury amid Bo Bichette, Kyle Tucker chase - Bolavip US

Blue Jays add former Red Sox pitcher while rehabbing injury amid Bichette, Tucker chase

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